Synthesis, characterization and antimicrobial evaluation of some new schiff, mannich and acetylenic Mannich bases incorporating a 1,2,4-triazole nucleus.

PubMed

Aouad, Mohamed R

2014-11-18

A series of Schiff and Mannich bases derived from 4-amino-5-(3-fluoro-phenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione were synthesized. The alkylation of 4-phenyl-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione with propargyl bromide afforded the corresponding thiopropargylated derivative which upon treatment with the appropriate secondary amines in the presence of CuCl2 furnished the desired acetylenic Mannich bases. The synthesized compounds were characterized on the basis of their spectral (IR, 1H- and 13C-NMR) data and evaluated for their biological activities. Some of the compounds were found to exhibit significant antimicrobial activity.

40 CFR 721.10321 - Bis[phenyl, 2H-1,3-benzoxazine]derivative (generic).

Code of Federal Regulations, 2014 CFR

2014-07-01

... Specific Chemical Substances § 721.10321 Bis[phenyl, 2H-1,3-benzoxazine]derivative (generic). (a) Chemical... as bis[phenyl, 2H-1,3-benzoxazine]derivative (PMN P-03-194) is subject to reporting under this... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Bis[phenyl, 2H-1,3-benzoxazine...

40 CFR 721.10321 - Bis[phenyl, 2H-1,3-benzoxazine]derivative (generic).

Code of Federal Regulations, 2013 CFR

2013-07-01

... Specific Chemical Substances § 721.10321 Bis[phenyl, 2H-1,3-benzoxazine]derivative (generic). (a) Chemical... as bis[phenyl, 2H-1,3-benzoxazine]derivative (PMN P-03-194) is subject to reporting under this... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Bis[phenyl, 2H-1,3-benzoxazine...

40 CFR 721.10321 - Bis[phenyl, 2H-1,3-benzoxazine]derivative (generic).

Code of Federal Regulations, 2012 CFR

2012-07-01

... Specific Chemical Substances § 721.10321 Bis[phenyl, 2H-1,3-benzoxazine]derivative (generic). (a) Chemical... as bis[phenyl, 2H-1,3-benzoxazine]derivative (PMN P-03-194) is subject to reporting under this... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Bis[phenyl, 2H-1,3-benzoxazine...

40 CFR 721.10539 - Bis[phenyl-2H-1,3-benzoxazine]derivative (generic).

Code of Federal Regulations, 2014 CFR

2014-07-01

... Specific Chemical Substances § 721.10539 Bis[phenyl-2H-1,3-benzoxazine]derivative (generic). (a) Chemical... as bis[phenyl-2H-1,3-benzoxazine]derivative (PMN P-02-653) is subject to reporting under this section... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Bis[phenyl-2H-1,3-benzoxazine...

40 CFR 721.10539 - Bis[phenyl-2H-1,3-benzoxazine]derivative (generic).

Code of Federal Regulations, 2013 CFR

2013-07-01

... Specific Chemical Substances § 721.10539 Bis[phenyl-2H-1,3-benzoxazine]derivative (generic). (a) Chemical... as bis[phenyl-2H-1,3-benzoxazine]derivative (PMN P-02-653) is subject to reporting under this section... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Bis[phenyl-2H-1,3-benzoxazine...

Crystal structure of fac-[2-(4-methyl-5-phenyl-pyridin-2-yl)phenyl-κ2C1,N]bis-[2-(pyridin-2-yl)phenyl-κ2C1,N]iridium(III).

PubMed

Lee, Chi-Heon; Moon, Suk-Hee; Park, Ki-Min; Kang, Youngjin

2016-12-01

In the title compound, [Ir(C 11 H 8 N) 2 (C 18 H 14 N)], the Ir III ion adopts a distorted octa-hedral coordination environment defined by three C , N -chelating ligands, one stemming from a 2-(4-phenyl-5-methyl-pyridin-2-yl)phenyl ligand and two from 2-(pyridin-2-yl)phenyl ligands, arranged in a facial manner. The Ir III ion lies almost in the equatorial plane [deviation = 0.0069 (15) Å]. In the crystal, inter-molecular π-π stacking inter-actions, as well as inter-molecular C-H⋯π inter-actions, are present, leading to a three-dimensional network.

Molecular structure, FT-IR, vibrational assignments, HOMO-LUMO, MEP, NBO analysis and molecular docking study of ethyl-6-(4-chlorophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate.

PubMed

Sheena Mary, Y; Yohannan Panicker, C; Sapnakumari, M; Narayana, B; Sarojini, B K; Al-Saadi, Abdulaziz A; Van Alsenoy, Christian; War, Javeed Ahmad

2015-03-05

The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of ethyl-6-(4-chlorophenyl)-4-(4-fluoro-phenyl)-2-oxocyclohex-3-ene-1-carboxylate have been investigated experimentally and theoretically using Gaussian09 software. The title compound was optimized using the HF and DFT levels of theory. The geometrical parameters are in agreement with the XRD data. The stability of the molecule has been analyzed by NBO analysis. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. Molecular electrostatic potential was performed by the DFT method. As can be seen from the MEP map of the title compound, regions having the negative potential are over the electro negative atoms, the region having the positive potential are over the phenyl rings and the remaining species are surrounded by zero potential. First hyperpolarizability is calculated in order to find its role in non linear optics. The title compound binds at the active sites of both CypD and β-secretase and the molecular docking results draw the conclusion that the compound might exhibit β-secretase inhibitory activity which could be utilized for development of new anti-alzheimeric drugs with mild CypD inhibitory activity. Copyright © 2014 Elsevier B.V. All rights reserved.

40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is subject...

40 CFR 721.275 - Halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Halogenated-N-(2-propenyl)-N... New Uses for Specific Chemical Substances § 721.275 Halogenated-N-(2-propenyl)-N-(substituted phenyl... identified generically as halogenated-N-(2-propenyl)-N-(substituted phenyl) acetamide (P-83-1085) is subject...

40 CFR 721.2465 - Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate.

Code of Federal Regulations, 2013 CFR

2013-07-01

...)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate. 721.2465 Section 721.2465 Protection of...-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate. (a) Chemical substance and significant...-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate (PMN P-00-1195; CAS No. 26694-69-9) is...

40 CFR 721.2465 - Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate.

Code of Federal Regulations, 2012 CFR

2012-07-01

...)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate. 721.2465 Section 721.2465 Protection of...-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate. (a) Chemical substance and significant...-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate (PMN P-00-1195; CAS No. 26694-69-9) is...

40 CFR 721.2465 - Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate.

Code of Federal Regulations, 2011 CFR

2011-07-01

...)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate. 721.2465 Section 721.2465 Protection of...-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate. (a) Chemical substance and significant...-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate (PMN P-00-1195; CAS No. 26694-69-9) is...

40 CFR 721.2465 - Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate.

Code of Federal Regulations, 2014 CFR

2014-07-01

...)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate. 721.2465 Section 721.2465 Protection of...-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate. (a) Chemical substance and significant...-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate (PMN P-00-1195; CAS No. 26694-69-9) is...

Esterification of phenyl acetic acid with p-cresol using metal cation exchanged montmorillonite nanoclay catalysts

PubMed Central

Bhaskar, M.; Surekha, M.; Suma, N.

2018-01-01

The liquid phase esterification of phenyl acetic acid with p-cresol over different metal cation exchanged montmorillonite nanoclays yields p-cresyl phenyl acetate. Different metal cation exchanged montmorillonite nanoclays (Mn+ = Al3+, Zn2+, Mn2+, Fe3+, Cu2+) were prepared and the catalytic activity was studied. The esterification reaction was conducted by varying molar ratio of the reactants, reaction time and catalyst amount on the yield of the ester. Among the different metal cation exchanged catalysts used, Al3+-montmorillonite nanoclay was found to be more active. The characterization of the material used was studied under different techniques, namely X-ray diffraction, scanning electron microscopy and thermogravimetric analysis. The product obtained, p-cresyl phenyl acetate, was identified by thin-layer chromotography and confirmed by Fourier transform infrared, 1H NMR and 13C NMR. The regeneration activity of used catalyst was also investigated up to fourth generation. PMID:29515855

Esterification of phenyl acetic acid with p-cresol using metal cation exchanged montmorillonite nanoclay catalysts.

PubMed

Bhaskar, M; Surekha, M; Suma, N

2018-02-01

The liquid phase esterification of phenyl acetic acid with p -cresol over different metal cation exchanged montmorillonite nanoclays yields p -cresyl phenyl acetate. Different metal cation exchanged montmorillonite nanoclays (M n +  = Al 3+ , Zn 2+ , Mn 2+ , Fe 3+ , Cu 2+ ) were prepared and the catalytic activity was studied. The esterification reaction was conducted by varying molar ratio of the reactants, reaction time and catalyst amount on the yield of the ester. Among the different metal cation exchanged catalysts used, Al 3+ -montmorillonite nanoclay was found to be more active. The characterization of the material used was studied under different techniques, namely X-ray diffraction, scanning electron microscopy and thermogravimetric analysis. The product obtained, p -cresyl phenyl acetate, was identified by thin-layer chromotography and confirmed by Fourier transform infrared, 1 H NMR and 13 C NMR. The regeneration activity of used catalyst was also investigated up to fourth generation.

LIQUID CHROMATOGRAPHIC DETERMINATION OF 5-(METHYLAMINO)-2-PHENYL-4-[3-(TRIFLUROMETHYL) PHENYL]-3-(2H)-FURANONE IN SOIL

EPA Science Inventory

A rapid, sensitive method is described for the determination of 5-(methylamino)-2-phenyl-4-[3-(trifluromethyl)phenyl]-3-(2H)-furanone RE-40885) concentrations in three soil types. he method consists of extraction of soil samples with methanol, filtration, liquid chromatographic s...

Studies on complex π-π and T-stacking features of imidazole and phenyl/p-halophenyl units in series of 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carboxamides and their carbonitrile derivatives: Role of halogens in tuning of conformation

NASA Astrophysics Data System (ADS)

Das, Aniruddha

2017-11-01

5-amino-1-(phenyl/p-halophenyl)imidazole-4-carboxamides (N-phenyl AICA) (2a-e) and 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carbonitriles (N-phenyl AICN) (3a-e) had been synthesized. X-ray crystallographic studies of 2a-e and 3a-e had been performed to identify any distinct change in stacking patterns in their crystal lattice. Single crystal X-ray diffraction studies of 2a-e revealed π-π stack formations with both imidazole and phenyl/p-halophenyl units in anti and syn parallel-displaced (PD)-type dispositions. No π-π stacking of imidazole occurred when the halogen substituent is bromo or iodo; π-π stacking in these cases occurred involving phenyl rings only. The presence of an additional T-stacking had been observed in crystal lattices of 3a-e. Vertical π-π stacking distances in anti-parallel PD-type arrangements as well as T-stacking distances had shown stacking distances short enough to impart stabilization whereas syn-parallel stacking arrangements had got much larger π-π stacking distances to belie any syn-parallel stacking stabilization. DFT studies had been pursued for quantifying the π-π stacking and T-stacking stabilization. The plotted curves for anti-parallel and T-stacked moieties had similarities to the 'Morse potential energy curve for diatomic molecule'. The minima of the curves corresponded to the most stable stacking distances and related energy values indicated stacking stabilization. Similar DFT studies on syn-parallel systems of 2b corresponded to no π-π stacking stabilization at all. Halogen-halogen interactions had also been observed to stabilize the compounds 2d, 2e and 3d. Nano-structural behaviour of the series of compounds 2a-e and 3a-e were thoroughly investigated.

Various applications of immobilized glucose oxidase and polyphenol oxidase in a conducting polymer matrix.

PubMed

Cil, M; Böyükbayram, A E; Kiralp, S; Toppare, L; Yağci, Y

2007-06-01

In this study, glucose oxidase and polyphenol oxidase were immobilized in conducting polymer matrices; polypyrrole and poly(N-(4-(3-thienyl methylene)-oxycarbonyl phenyl) maleimide-co-pyrrole) via electrochemical method. Fourier transform infrared and scanning electron microscope were employed to characterize the copolymer of (N-(4-(3-thienyl methylene)-oxycarbonyl phenyl) maleimide) with pyrrole. Kinetic parameters, maximum reaction rate and Michealis-Menten constant, were determined. Effects of temperature and pH were examined for immobilized enzymes. Also, storage and operational stabilities of enzyme electrodes were investigated. Glucose and polyphenol oxidase enzyme electrodes were used for determination of the glucose amount in orange juices and human serum and phenolic amount in red wines, respectively.

Crystal structures of 4-meth-oxy-N-(4-methyl-phenyl)benzene-sulfonamide and N-(4-fluoro-phenyl)-4-meth-oxy-benzene-sulfonamide.

PubMed

Rodrigues, Vinola Z; Preema, C P; Naveen, S; Lokanath, N K; Suchetan, P A

2015-11-01

Crystal structures of two N-(ar-yl)aryl-sulfonamides, namely, 4-meth-oxy-N-(4-methyl-phen-yl)benzene-sulfonamide, C14H15NO3S, (I), and N-(4-fluoro-phen-yl)-4-meth-oxy-benzene-sulfonamide, C13H12FNO3S, (II), were determined and analyzed. In (I), the benzene-sulfonamide ring is disordered over two orientations, in a 0.516 (7):0.484 (7) ratio, which are inclined to each other at 28.0 (1)°. In (I), the major component of the sulfonyl benzene ring and the aniline ring form a dihedral angle of 63.36 (19)°, while in (II), the planes of the two benzene rings form a dihedral angle of 44.26 (13)°. In the crystal structure of (I), N-H⋯O hydrogen bonds form infinite C(4) chains extended in [010], and inter-molecular C-H⋯πar-yl inter-actions link these chains into layers parallel to the ab plane. The crystal structure of (II) features N-H⋯O hydrogen bonds forming infinite one dimensional C(4) chains along [001]. Further, a pair of C-H⋯O inter-molecular inter-actions consolidate the crystal packing of (II) into a three-dimensional supra-molecular architecture.

cis-Bis(O-methyl-dithio-carbonato-κ(2) S,S')bis-(tri-phenyl-phosphane-κP)ruthenium(II).

PubMed

Valerio-Cárdenas, Cintya; Hernández-Ortega, Simón; Reyes-Martínez, Reyna; Morales-Morales, David

2013-01-01

In the title compound, [Ru(CH3OCS2)2(C18H15P)2], the Ru(II) atom is in a distorted octa-hedral coordination by two xanthate anions (CH3OCS2) and two tri-phenyl-phosphane (PPh3) ligands. Both bidentate xanthate ligands coordinate the Ru(II) atom with two slightly different Ru-S bond lengths but with virtually equal bite angles [71.57 (4) and 71.58 (3)°]. The packing of the complexes is assured by C-H⋯O and C-H⋯π inter-actions.

Electrochemical synthesis, characterization and electrochromic properties of a copolymer based on 1,4-bis(2-thienyl)naphthalene and pyrene

NASA Astrophysics Data System (ADS)

Wang, Bin; Zhao, Jinsheng; Cui, Chuansheng; Wang, Min; Wang, Zhong; He, Qingpeng

2012-05-01

Electrochemical copolymerization of 1,4-bis(2-thienyl)naphthalene (BTN) with pyrene is carried out in acetonitrile (ACN) solution containing sodium perchlorate (NaClO4) as a supporting electrolyte. Characterizations of the resulting copolymer P(BTN-co-pyrene) are performed by cyclic voltammetry (CV), UV-vis spectroscopy, Fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM). The P(BTN-co-pyrene) film has distinct electrochromic properties and exhibits three different colors (yellowish green, green and blue) under various potentials. Maximum contrast (ΔT%) and response time of the copolymer film are measured as 37.8% and 1.71 s at 687 nm. An electrochromic device (ECD) based on P(BTN-co-pyrene) and poly(3,4-ethylenedioxythiophene) (PEDOT) is constructed and characterized. Neutral state of device shows green color while oxidized state reveals blue color. This ECD shows a maximum optical contrast (ΔT%) of 24.4% with a response time of 0.43 s at 635 nm. The coloration efficiency (CE) of the device is calculated to be 349 cm2 C-1 at 635 nm. In addition, the ECD also has satisfactory optical memories and redox stability.

Spectrophotometric determination of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid in pure form and in pharmaceuticals

NASA Astrophysics Data System (ADS)

Bazel, Yaroslav; Hunka, Iryna; Kormosh, Zholt; Andruch, Vasil

2009-12-01

A new sensitive and selective spectrophotometric method has been developed for the determination of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid in pharmaceuticals in the presence of nicotinic acid. The method is based on the reaction of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid with 1,3,3-trimethyl-5-phenyl-2-[3-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-propenyl]-3 H-indolium chloride (PIC) followed by the extraction of the formed ion associate into toluene and spectrophotometric detection at 581 nm. Appropriate experimental conditions were found to be pH 7.8-9.8 and 3.6 × 10 -4 mol L -1 of PIC. The molar absorptivity is 5.0 × 10 -4 L mol -1 cm -1. The absorbance obeys Beer's law in the range 0.61-12.60 μg mL -1 of [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid, and the detection limit calculated from a blank test was 0.20 μg mL -1.

Protection of 2-(3-Thienyl)ethanol with 3-Thienylacetic Acid and Hard Cross- Linked Conducting Films by Electropolymerization of the Ester

NASA Technical Reports Server (NTRS)

Leventis, Nicholas; Dass, Amala; Mulik, Sudir; Sotiriou-Leventis, Chariklia

2005-01-01

The ester (compound 1) of 2-(3-thienyl)ethanol (T-etOH) with 3-thienylacetic acid was synthesized as a monomer whose two thiophene groups could be electropolymerized independently, becoming members of different polymer chains in a highly-crosslinked highly-insoluble polymer. Indeed, 1 was electropolymerized successfully alone and together with 3-methylthiophene (3MeT). Films of poly(1) are hard (3H, as opposed to less than 6B for poly(3MeT)), and the close proximity of the polymeric strands creates pi-stacking interactions. The behavior of 1 suggests that by: (a) limiting the potential used for the oxidation of monomeric esters of T-etOH at the foot of their oxidation waves (less than 1.8 V vs. Ag/AgCl); and, (b) compensating for the decrease in the electrogenerated radical concentration by increasing the monomer concentration, practically all esters of T-etOH should be electropolymerizable. This was confirmed by durable film formation from the archetypical ester of T-etOH, the 2-(3-thienyl)ethyl acetate (T-etOAc), whose homo-electropolymerization is reported for the first time.

Vibrational spectroscopy (FT-IR and Laser-Raman) investigation, and computational (M06-2X and B3LYP) analysis on the structure of 4-(3-fluorophenyl)-1-(propan-2-ylidene)-thiosemicarbazone.

PubMed

Sert, Yusuf; Miroslaw, Barbara; Çırak, Çağrı; Doğan, Hatice; Szulczyk, Daniel; Struga, Marta

2014-07-15

In this study, the experimental and theoretical vibrational spectral analysis of 4-(3-fluorophenyl)-1-(propan-2-ylidene)-thiosemicarbazone have been carried out. The experimental FT-IR (4000-400 cm(-1)) and Laser-Raman spectra (4000-100 cm(-1)) have been recorded for the solid state samples. The theoretical vibrational frequencies and the optimized geometric parameters (bond lengths and angles) have been calculated for gas phase using density functional theory (DFT/B3LYP: Becke, 3-parameter, Lee-Yang-Parr) and M06-2X (the highly parametrized, empirical exchange correlation function) quantum chemical methods with 6-311++G(d,p) basis set. The diversity in molecular geometry of fluorophenyl substituted thiosemicarbazones has been discussed based on the X-ray crystal structure reports and theoretical calculation results from the literature. The assignments of the vibrational frequencies have been done on the basis of potential energy distribution (PED) analysis by using VEDA4 software. A good correlation was found between the computed and experimental geometric and vibrational data. In addition, the highest occupied (HOMO) and lowest unoccupied (LUMO) molecular orbital energy levels and other related molecular energy values of the compound have been determined using the same level of theoretical calculations. Copyright © 2014 Elsevier B.V. All rights reserved.

Synthesis of (+)-Didemniserinolipid B: Application of a 2-Allyl-4-fluorophenyl Auxiliary for Relay Ring-Closing Metathesis

PubMed Central

Marvin, Christopher C.; Voight, Eric A.; Suh, Judy M.; Paradise, Christopher L.; Burke, Steven D.

2009-01-01

The synthesis of didemniserinolipid B utilizing a ketalization/ring-closing metathesis (K/RCM) strategy is described. In the course of this work, a novel 2-allyl-4-fluorophenyl auxiliary for relay ring-closing metathesis (RRCM) was developed which increased the yield of the RCM. The resulting 6,8-dioxabicyclo[3.2.1]octene core was selectively functionalized by complimentary dihydroxylation and epoxidation routes to install the C10 axial alcohol. This bicyclic ketal core was further functionalized by etherification and an alkene cross metathesis with an unsaturated α-phenylselenyl ester en route to completing the total synthesis. PMID:18811201

Synthesis and NLO studies of novel (2E)-1-(2-bromo-4,5-dimethoxyphenyL)-3-(3-Bromo-4-Fluorophenyl)Prop-2-en-1-one single crystal

NASA Astrophysics Data System (ADS)

Shruthi, C.; Ravindrachary, V.; Prasad, D. Jagadeesh; Guruswamy, B.; Hegde, Shreedatta

2017-05-01

A novel organic nonlinear optical (NLO) material (2E)-1-(2-Bromo-4,5-Dimethoxyphenyl)-3-(3-Bromo-4-Fluorophenyl)Prop-2-en-1-one has been synthesized using Claisen-Schmidth condensation method. The chemical structure of the compound was confirmed by recording its FT-IR spectrum and the functional groups were identified. Single crystals were grown by slow evaporation method and the single crystal XRD study reveals that the compound crystallizes in the monoclinic crystal system with a space group -P 2yn. The observed cell parameters are a = 9.346(5) A°, b = 12.953(7) A°, c = 14.355(8) A°, α = 90°, β = 108.379°(9), γ = 90°. UV-Visible study shows that the compound is transparent in the entire visible region and the absorption takes place in the UV range. The Non linear optical efficiency of the crystal was estimated and it is found to be 0.5 times that of standard KDP crystal.

O-Phenyl Carbamate and Phenyl Urea Thiiranes as Selective Matrix Metalloproteinase-2 Inhibitors that Cross the Blood-Brain Barrier

PubMed Central

Gooyit, Major; Song, Wei; Mahasenan, Kiran V.; Lichtenwalter, Katerina; Suckow, Mark A.; Schroeder, Valerie A.; Wolter, William R.; Mobashery, Shahriar; Chang, Mayland

2013-01-01

Brain metastasis occurs in 20% to 40% of cancer patients. Treatment is mostly palliative and the inability of most drugs to penetrate the brain presents one of the greatest challenges in the development of therapeutics for brain metastasis. Matrix metalloproteinase-2 (MMP-2) plays important roles in invasion and vascularization of the central nervous system and represents a potential target for treatment of brain metastasis. Carbonate, O-phenyl carbamate, urea, and N-phenyl carbamate derivatives of SB-3CT, a selective and potent gelatinase inhibitor were synthesized and evaluated. The O-phenyl carbamate and urea variants were selective and potent inhibitors of MMP-2. Carbamate 5b was metabolized to the potent gelatinase inhibitor 2, which was present at therapeutic concentrations in the brain. In contrast, phenyl urea 6b crossed the blood-brain barrier, however higher doses would result in therapeutic brain concentrations. Carbamate 5b and urea 6b show potential for intervention of MMP-2-dependent diseases, such as brain metastasis. PMID:24028490

Synthetic, Infrared, 1Hand 13CNMR Spectral Studies on N-(p-Substituted Phenyl)-p-Substituted Benzenesulphonamides, p-X'C6H4SO2NH- (p-XC6H4), where X' or X = H, CH3, C2H5, F, Cl or Br

NASA Astrophysics Data System (ADS)

Gowda, B. Thimme; Jayalakshmi, K. L.; Shetty, Mahesha

2004-05-01

Thirty N-(p-substituted phenyl)-p-substituted benzenesulphonamides of the general formula, p-X'C6H4SO2NH(p-XC6H4), where X' or X = H, CH3, C2H5, F, Cl or Br, are synthesised and their infrared spectra in the solid state and 1H and 13C NMR spectra in solution are measured. The N-H stretching vibrational frequencies, νN-H vary in the range 3334 - 3219 cm-1, while the asymmetric and symmetric SO2 vibrations appear in the ranges 1377 - 1311 cm-1 and 1182 - 1151 cm-1, respectively. The compounds exhibit S-N and C-N stretching vibrational absorptions in the ranges 937 - 898 cm-1 and 1310 - 1180 cm-1, respectively. There are no particular trends in the variation of these frequencies on substitution with either electron withdrawing or electron donating groups. The 1H and 13C chemical shifts of N-(p-substituted phenyl)-p-substituted benzenesulphonamides, are assigned to various protons and carbons of the two benzene rings. Further, incremental shifts of the ring protons and carbons due to -SO2NH(p-XC6H4) groups in the compounds of the formula, C6H5SO2NH(p-XC6H4), and p-X'C6H4SO2- and p-X'C6H4SO2NH- groups in the compounds of the formula, p-X'C6H4SO2NH(C6H5) are computed and used to calculate the 1H and 13C chemical shifts of the parallely substituted compounds of the general formula p-X'C6H4SO2NH(p-XC6H4). The computed values agree well with the observed chemical shifts. The above incremental shifts are found to correlate with the Hammett substituent parameters.

Donor-acceptor-donor thienyl/bithienyl-benzothiadiazole/quinoxaline model oligomers: experimental and theoretical studies.

PubMed

Pina, João; de Melo, J Seixas; Breusov, D; Scherf, Ullrich

2013-09-28

A comprehensive spectral and photophysical investigation of four donor-acceptor-donor (DAD) oligomers consisting of electron-deficient 2,1,3-benzothiadiazole or quinoxaline moieties linked to electron-rich thienyl or bithienyl units has been undertaken. Additionally, a bis(dithienyl) substituted naphthalene was also investigated. The D-A-D nature of these oligomers resulted in the presence of an intramolecular charge transfer (ICT) state, which was further substantiated by solvatochromism studies (analysis with the Lippert-Mataga formalism). Hereby, significant differences have been obtained for the fluorescence quantum yields of the oligomers in the non-polar solvent methylcyclohexane vs. the polar ethanol. The study was further complemented with the determination of the optimized ground-state molecular geometries for the oligomers together with the prediction of the lowest vertical one-electron excitation energy and the relevant molecular orbital contours using DFT calculations. The electronic transitions show a clear HOMO to LUMO charge-transfer character. In contrast to the thiophene oligomers (the oligothiophenes with n = 1-7), where the intersystem crossing (ISC) yield decreases with n, the studied DAD oligomers were found to show an increase in the ISC efficiency with the number of (donor) thienyl units.

Synthesis and antimicrobial evaluation of ester-linked 1,4-disubstituted 1,2,3-triazoles with a furyl/thienyl moiety.

PubMed

Kaushik, C P; Luxmi, Raj; Singh, Dharmendra; Kumar, Ashwani

2017-02-01

Twenty ester-linked 1,4-disubstituted 1,2,3-triazoles having a furyl/thienyl moiety have been synthesized from heteroaryl prop-2-yn-1-yl carboxylate and aromatic azides via a Cu(I) catalyzed 1,3-dipolar cycloaddition. All the synthesized compounds were characterized by FTIR, [Formula: see text]H NMR, [Formula: see text]C NMR spectroscopy and HRMS. Synthesized triazoles were tested in vitro for antimicrobial evaluation against Gram-negative bacteria-Escherichia coli, Enterobacter aerogenes and Klebsiella pneumoniae; Gram-positive bacteria-Staphylococcus aureus and two fungal strains-Candida albicans and Aspergillus niger, reflecting moderate to good activity. The structure of compound 6f was also confirmed by X-ray crystallography (CCDC 1469326).

A repertoire of pyridinium-phenyl-methyl cross-talk through a cascade of intramolecular electrostatic interactions.

PubMed

Acharya, P; Plashkevych, O; Morita, C; Yamada, S; Chattopadhyaya, J

2003-02-21

Direct intramolecular cation-pi interaction between phenyl and pyridinium moieties in 1a(+) has been experimentally evidenced through pH-dependent (1)H NMR titration. The basicity of the pyridinyl group (pK(a) 2.9) in 1a can be measured both from the pH-dependent chemical shifts of the pyridinyl protons as well as from the protons of the neighboring phenyl and methyl groups as a result of electrostatic interaction between the phenyl and the pyridinium ion in 1a(+) at the ground state. The net result of this nearest neighbor electrostatic interaction is that the pyridinium moiety in 1a becomes more basic (pK(a) 2.92) compared to that in the standard 2a (pK(a) 2.56) as a consequence of edge-to-face cation (pyridinium)-pi (phenyl) interaction, giving a free energy of stabilization (DeltaDeltaG(o)pKa) of -2.1 kJ mol(-1). The fact that the pH-dependent downfield shifts of the phenyl and methyl protons give the pK(a) of the pyridine moiety of 1a also suggests that the nearest neighbor cation (pyridinium)-pi (phenyl) interaction also steers the CH (methyl)-pi (phenyl) interaction in tandem. This means that the whole pyridine-phenyl-methyl system in 1a(+) is electronically coupled at the ground state, cross-modulating the physicochemical property of the next neighbor by using the electrostatics as the engine, and the origin of this electrostatics is a far away point in the molecule-the pyridinyl-nitrogen. The relative chemical shift changes and the pK(a) differences show that the cation (pyridinium)-pi (phenyl) interaction is indeed more stable (DeltaDeltaG(o)pKa = -2.1 kJ mol(-1)) than that of the CH (methyl)-pi (phenyl) interaction (DeltaDeltaG(o)pKa = -0.8 kJ mol(-1)). Since the pK(a) of the pyridine moiety in 1a is also obtained through the pH-dependent shifts of both phenyl and methyl protons, it suggests that the net electrostatic mediated charge transfer from the phenyl to the pyridinium and its effect on the CH (methyl)-pi (phenyl) interaction corresponds to DeltaG(o)p

2,2-Bis[(2-halo-4-aminophenoxy)phenyl]-hexafluoropropane

NASA Technical Reports Server (NTRS)

Jones, Robert J. (Inventor); Chang, Glenn E. C. (Inventor)

1985-01-01

There are provided the aromatic diamines 2,2-bis-[(2-halo-4-aminophenoxy)-phenyl]hexafluoropropane, where the attached ortho halogen is preferably chlorine, and 4,4'-bis(4-aminophenoxy)biphenyl, as novel monomers for polyimide polymerizations. The former, when reacted with 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, provides a polyimide having exceptional high-temperature performance. The latter diamine is a low-cost monomer for polyimide production.

Synthesis and photovoltaic properties of 2,6-bis(2-thienyl) benzobisazole and 4,8-bis(thienyl)-benzo[1,2- B :4,5- B' ]dithiophene copolymers

DOE Office of Scientific and Technical Information (OSTI.GOV)

Bhuwalka, Achala; Ewan, Monique D.; Elshobaki, Moneim

2015-08-22

In an effort to design efficient low-cost polymers for use in organic photovoltaic cells the easily prepared donor–acceptor–donor triad of a either cis-benzobisoxazole, trans-benzobisoxazole or trans-benzobisthiazole flanked by two thiophene rings was combined with the electron-rich 4,8-bis(5-(2-ethylhexyl)-thien-2-yl)-benzo[1,2-b:4,5-b']dithiophene. The electrochemical, optical, morphological, charge transport, and photovoltaic properties of the resulting terpolymers were investigated. Although the polymers differed in the arrangement and/or nature of the chalcogens, they all had similar highest occupied molecular orbital energy levels (-5.2 to -5.3 eV) and optical band gaps (2.1–2.2 eV). However, the lowest unoccupied molecular orbital energy levels ranged from -3.1 to -3.5 eV. When themore » polymers were used as electron donors in bulk heterojunction photovoltaic devices with PC71BM ([6,6]-phenyl C71-butyric acid methyl ester) as the acceptor, the trans-benzobisoxazole polymer had the best performance with a power conversion efficiency of 2.8%.« less

Discovery of N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine derivatives as novel CK1 inhibitors using common-feature pharmacophore model based virtual screening and hit-to-lead optimization.

PubMed

Yang, Ling-Ling; Li, Guo-Bo; Yan, Heng-Xiu; Sun, Qi-Zheng; Ma, Shuang; Ji, Pan; Wang, Ze-Rong; Feng, Shan; Zou, Jun; Yang, Sheng-Yong

2012-10-01

Aberrant activation of casein kinase 1 (CK1) has been demonstrated to be implicated in the pathogenesis of cancer and various central nervous system disorders. Discovery of CK1 inhibitors has thus attracted much attention in recent years. In this account, we describe the discovery of N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine derivatives as novel CK1 inhibitors. An optimal common-feature pharmacophore hypothesis, termed Hypo2, was firstly generated, followed by virtual screening using Hypo2 against several chemical databases. One of the best hit compounds, N6-(4-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine, was chosen for the subsequent hit-to-lead optimization under the guide of Hypo2, which led to the discovery of a new lead compound (1-(3-(3-amino-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-3-(3-chloro-4-fluorophenyl)urea) that potently inhibits CK1 with an IC(50) value of 78 nM. Copyright © 2012 Elsevier Masson SAS. All rights reserved.

3-Methyl-7-(2-thienyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione: pi-stacked bilayers built from N-H...O, C-H...O and C-H...pi hydrogen bonds.

PubMed

Trilleras, Jorge; Quiroga, Jairo; Cobo, Justo; Glidewell, Christopher

2009-06-01

In the title compound, C(12)H(9)N(3)O(2)S, the thienyl substituent is disordered over two sets of sites with occupancies of 0.749 (3) and 0.251 (3). A combination of N-H...O, C-H...O and C-H...pi hydrogen bonds links the molecules into bilayers and these bilayers are themselves linked into a continuous structure by pi-pi stacking interactions.

Structure-activity relationships of substituted N-benzyl piperidines in the GBR series: Synthesis of 4-(2-(bis(4-fluorophenyl)methoxy)ethyl)-1-(2-trifluoromethylbenzyl)piperidine, an allosteric modulator of the serotonin transporter.

PubMed

Boos, Terrence L; Greiner, Elisabeth; Calhoun, W Jason; Prisinzano, Thomas E; Nightingale, Barbara; Dersch, Christina M; Rothman, Richard B; Jacobson, Arthur E; Rice, Kenner C

2006-06-01

A series of 4-(2-(bis(4-fluorophenyl)methoxy)ethyl)-(substituted benzyl) piperidines with substituents at the ortho and meta positions in the aromatic ring of the N-benzyl side chain were synthesized and their affinities and selectivities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) were determined. One analogue, 4-(2-(bis(4-fluorophenyl)methoxy)ethyl)-1-(2-trifluoromethylbenzyl)piperidine (the C(2)-trifluoromethyl substituted compound), has been found to act as an allosteric modulator of hSERT binding and function. It had little affinity for any of the transporters. Several compounds showed affinity for the DAT in the low nanomolar range and displayed a broad range of SERT/DAT selectivity ratios and very little affinity for the NET. The pharmacological tools provided by the availability of compounds with varying transporter affinity and selectivity could be used to obtain additional information about the properties a compound should have to act as a useful pharmacotherapeutic agent for cocaine addiction and help unravel the pharmacological mechanisms relevant to stimulant abuse.

Inserting Thienyl Linkers into Conjugated Molecules for Efficient Multilevel Electronic Memory: A New Understanding of Charge-Trapping in Organic Materials.

PubMed

Li, Yang; Li, Hua; He, Jinghui; Xu, Qingfeng; Li, Najun; Chen, Dongyun; Lu, Jianmei

2016-03-18

The practical application of organic memory devices requires low power consumption and reliable device quality. Herein, we report that inserting thienyl units into D-π-A molecules can improve these parameters by tuning the texture of the film. Theoretical calculations revealed that introducing thienyl π bridges increased the planarity of the molecular backbone and extended the D-A conjugation. Thus, molecules with more thienyl spacers showed improved stacking and orientation in the film state relative to the substrates. The corresponding sandwiched memory devices showed enhanced ternary memory behavior, with lower threshold voltages and better repeatability. The conductive switching and variation in the performance of the memory devices were interpreted by using an extended-charge-trapping mechanism. Our study suggests that judicious molecular engineering can facilitate control of the orientation of the crystallite in the solid state to achieve superior multilevel memory performance. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

cis-Bis(O-methyl­dithio­carbonato-κ2 S,S′)bis­(tri­phenyl­phosphane-κP)ruthenium(II)

PubMed Central

Valerio-Cárdenas, Cintya; Hernández-Ortega, Simón; Reyes-Martínez, Reyna; Morales-Morales, David

2013-01-01

In the title compound, [Ru(CH3OCS2)2(C18H15P)2], the RuII atom is in a distorted octa­hedral coordination by two xanthate anions (CH3OCS2) and two tri­phenyl­phosphane (PPh3) ligands. Both bidentate xanthate ligands coordinate the RuII atom with two slightly different Ru—S bond lengths but with virtually equal bite angles [71.57 (4) and 71.58 (3)°]. The packing of the complexes is assured by C—H⋯O and C—H⋯π inter­actions. PMID:24046578

Copper(II) complexes of N-(2-{[(2E)-2-(2-Hydroxy-(5-substituted)-benzylidene)-hydrazino]carbonyl}phenyl)benzamide ligands and heterocyclic coligands

NASA Astrophysics Data System (ADS)

Chavan, S. S.; Sawant, V. A.; Jadhav, A. N.

2014-01-01

Some copper(II) complexes of the type [Cu(L1-3)(phen]ṡCH2Cl2 (1a-3a) and [Cu(L1-3) (bipy)]ṡCH2Cl2 (1b-3b) (where L1 = N-(2-{[(2E)-2-(2-Hydroxy-benzylidene)-hydrazino]carbonyl}phenyl)benzamide, L2 = N-(2-{[(2E)-2-(2-Hydroxy-(5-bromo)-benzylidene)-hydrazino]carbonyl}phenyl)benzamide, L3 = N-(2-{[(2E)-2-(2-Hydroxy-(5-methoxy)-benzylidene)-hydrazino]carbonyl}phenyl)benzamide; phen = 1,10-phenanthroline, bipy = 2,2‧-bipyridine) have been prepared and characterized on the basis of elemental analyses, IR, UV-Vis and EPR spectral studies. IR spectra indicate that the ligand L1-3 exists in the keto form in the solid state, while at the time of complexation, it tautomerises into enol form. The single crystal X-ray diffraction study of the representative complex [Cu(L1) (phen)]ṡCH2Cl2 (1a) reveals the distorted square pyramidal geometry around copper(II). Crystal data of (1a): space group = P21/n, a = 11.5691(16) Å, b = 11.0885(15) Å, c = 24.890(4) Å, V = 3166.2(8) Å3, Z = 4. The electrochemical behavior of all the complexes indicate that the phen complexes appears at more positive potential as compared to those for bipy complexes, as a consequence of its stronger π acidic character. All the complexes exhibit blue-green emission as a result of the fluorescence from the intra-ligand (π → π∗) emission excited state.

In search of selective P2 receptor ligands: interaction of dihydropyridine derivatives at recombinant rat P2X(2) receptors.

PubMed

Jacobson, K A; Kim, Y C; King, B F

2000-07-03

1,4-Dihydropyridines are regarded as privileged structures for drug design, i.e. they tend to bind to a wide variety of receptor sites. We have shown that upon appropriate manipulation of the substituent groups on a 1,4-dihydropyridine template, high affinity and selectivity for the A(3) subtype of adenosine receptors ('P1 receptors') may be attained. In the present study we have begun to extend this approach to P2 receptors which are activated by ATP and other nucleotides. Nicardipine, a representative dihydropyridine, used otherwise as an L-type calcium channel blocker, was shown to be an antagonist at recombinant rat P2X(2) (IC(50)=25 microM) and P2X(4) (IC(50) approximately 220 microM) receptors expressed in Xenopus oocytes. Thus, this class of compounds represents a suitable lead for enhancement of affinity through chemical synthesis. In an attempt to modify the 1,4-dihydropyridine structure with a predicted P2 receptor recognition moiety, we have replaced one of the ester groups with a negatively charged phosphonate group. Several 4-phenyl-5-phosphonato-1,4-dihydropyridine derivatives, MRS 2154 (2, 6-dimethyl), MRS 2155 (6-methyl-2-phenyl), and MRS 2156 (2-methyl-6-phenyl), were synthesized through three component condensation reactions. These derivatives were not pure antagonists of the effects of ATP at P2X(2) receptors, rather were either inactive (MRS 2156) or potentiated the effects of ATP in a concentration-dependent manner (MRS 2154 in the 0.3-10 microM range and MRS 2155 at >1 microM). Antagonism of the effects of ATP at P2X(2) receptor superimposed on the potentiation was also observed at >10 microM (MRS 2154) or 0.3-1 microM (MRS 2155). Thus, while a conventional dihydropyridine, nicardipine, was found to antagonize rat P2X(2) receptors ninefold more potently than P2X(4) receptors, the effects of novel, anionic 5-phosphonate analogues at the receptor were more complex.

Synthesis and In Vitro Cytotoxicity of the 4-(Halogenoanilino)-6-bromoquinazolines and Their 6-(4-Fluorophenyl) Substituted Derivatives as Potential Inhibitors of Epidermal Growth Factor Receptor Tyrosine Kinase

PubMed Central

Paumo, Hugues K.

2017-01-01

Series of the 2-unsubstituted and 2-(4-chlorophenyl)–substituted 4-anilino-6-bromoquinazolines and their 6-(4-fluorophenyl)–substituted derivatives were evaluated for in vitro cytotoxicity against MCF-7 and HeLa cells. The 2-unsubstituted 4-anilino-6-bromoquinazolines lacked activity, whereas most of their 2-(4-chlorophenyl) substituted derivatives were found to exhibit significant cytotoxicity and selectivity against HeLa cells. Replacement of bromine with 4-fluorophenyl group for the 2-unsubstituted 4-anilinoquinazolines resulted in superior activity against HeLa cells compared to Gefitinib. The presence of a 4-fluorophenyl group in the 2-(4-chlorophenyl) substituted derivatives led to increased cytotoxicity against HeLa cells, except for the 3-chloroanilino derivative. The most active compounds, namely, 3g, 3l, and 4l, were found to exhibit a moderate to significant inhibitory effect against epidermal growth factor receptor tyrosine kinase (EGFR-TK). The EGFR molecular docking model suggested that these compounds are nicely bound to the region of EGFR. PMID:29156606

(13)C NMR substituent-induced chemical shifts in 4-(substituted phenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-ones (thiones).

PubMed

Kara, Yesim Saniye

2015-01-01

In the present, study mostly novel ten 4-(substituted phenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-ones and ten 4-(substituted phenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-thiones were synthesized. These oxadiazole derivatives were characterized by IR, (1)H NMR, (13)C NMR and elemental analyses. Their (13)C NMR spectra were measured in Deuterochloroform (CDCl3). The correlation analysis for the substituent-induced chemical shift (SCS) with Hammett substituent constants (σ), Brown Okamoto substituent constants (σ(+), σ(-)), inductive substituent constants (σI) and different of resonance substituent constants (σR, σR(o)) were performed using SSP (single substituent parameter), DSP (dual substituent parameter) and DSP-NLR (dual substituent parameter-non-linear resonance) methods, as well as single and multiple regression analysis. Negative ρ values were found for all correlations (reverse substituent effect). The results of all statistical analyses, (13)C NMR chemical shift of CN, CO and CS carbon of oxadiazole rings have shown satisfactory correlation. Copyright © 2015 Elsevier B.V. All rights reserved.

Crystal structure of 3-{1′-[3,5-bis­(tri­fluoro­meth­yl)phen­yl]ferrocenyl}-4-bromo­thio­phene

PubMed Central

Poppitz, Elisabeth A.; Korb, Marcus; Lang, Heinrich

2014-01-01

The mol­ecular structure of the title compound, [Fe(C9H6BrS)(C13H7F6)], consists of a ferrocene backbone with a bis­(tri­fluoro­meth­yl)phenyl group at one cyclo­penta­dienyl ring and a thio­phene heterocycle at the other cyclo­penta­dienyl ring. The latter is disordered over two sets of sites in a 0.6:0.4 ratio. In the crystal structure, intra­molecular π–π inter­actions between the thienyl and the phenyl substituent [centroid–centroid distance 3.695 (4) Å] and additional weak T-shaped π–π inter­actions between the thienyl and the phenyl-substituted cyclo­penta­dienyl ring [4.688 (6) Å] consolidate the crystal packing. PMID:25484662

Single‐Molecule Conductance Studies of Organometallic Complexes Bearing 3‐Thienyl Contacting Groups

PubMed Central

Bock, Sören; Al‐Owaedi, Oday A.; Eaves, Samantha G.; Milan, David C.; Lemmer, Mario; Skelton, Brian W.; Osorio, Henrry M.; Nichols, Richard J.; Higgins, Simon J.; Cea, Pilar; Long, Nicholas J.; Albrecht, Tim

2017-01-01

Abstract The compounds and complexes 1,4‐C6H4(C≡C‐cyclo‐3‐C4H3S)2 (2), trans‐[Pt(C≡C‐cyclo‐3‐C4H3S)2(PEt3)2] (3), trans‐[Ru(C≡C‐cyclo‐3‐C4H3S)2(dppe)2] (4; dppe=1,2‐bis(diphenylphosphino)ethane) and trans‐[Ru(C≡C‐cyclo‐3‐C4H3S)2{P(OEt)3}4] (5) featuring the 3‐thienyl moiety as a surface contacting group for gold electrodes have been prepared, crystallographically characterised in the case of 3–5 and studied in metal|molecule|metal junctions by using both scanning tunnelling microscope break‐junction (STM‐BJ) and STM‐I(s) methods (measuring the tunnelling current (I) as a function of distance (s)). The compounds exhibit similar conductance profiles, with a low conductance feature being more readily identified by STM‐I(s) methods, and a higher feature by the STM‐BJ method. The lower conductance feature was further characterised by analysis using an unsupervised, automated multi‐parameter vector classification (MPVC) of the conductance traces. The combination of similarly structured HOMOs and non‐resonant tunnelling mechanism accounts for the remarkably similar conductance values across the chemically distinct members of the family 2–5. PMID:27897344

Copper(II) complexes of N-(2-{[(2E)-2-(2-Hydroxy-(5-substituted)-benzylidene)-hydrazino]carbonyl}phenyl)benzamide ligands and heterocyclic coligands.

PubMed

Chavan, S S; Sawant, V A; Jadhav, A N

2014-01-03

Some copper(II) complexes of the type [Cu(L1-3)(phen]·CH2Cl2 (1a-3a) and [Cu(L1-3) (bipy)]·CH2Cl2 (1b-3b) (where L1=N-(2-{[(2E)-2-(2-Hydroxy-benzylidene)-hydrazino]carbonyl}phenyl)benzamide, L2=N-(2-{[(2E)-2-(2-Hydroxy-(5-bromo)-benzylidene)-hydrazino]carbonyl}phenyl)benzamide, L3=N-(2-{[(2E)-2-(2-Hydroxy-(5-methoxy)-benzylidene)-hydrazino]carbonyl}phenyl)benzamide; phen=1,10-phenanthroline, bipy=2,2'-bipyridine) have been prepared and characterized on the basis of elemental analyses, IR, UV-Vis and EPR spectral studies. IR spectra indicate that the ligand L1-3 exists in the keto form in the solid state, while at the time of complexation, it tautomerises into enol form. The single crystal X-ray diffraction study of the representative complex [Cu(L1) (phen)]·CH2Cl2 (1a) reveals the distorted square pyramidal geometry around copper(II). Crystal data of (1a): space group=P21/n, a=11.5691(16) Å, b=11.0885(15) Å, c=24.890(4) Å, V=3166.2(8) Å(3), Z=4. The electrochemical behavior of all the complexes indicate that the phen complexes appears at more positive potential as compared to those for bipy complexes, as a consequence of its stronger π acidic character. All the complexes exhibit blue-green emission as a result of the fluorescence from the intra-ligand (π→π(*)) emission excited state. Copyright © 2013 Elsevier B.V. All rights reserved.

Deepening the Topology of the Translocator Protein Binding Site by Novel N,N-Dialkyl-2-arylindol-3-ylglyoxylamides.

PubMed

Barresi, Elisabetta; Bruno, Agostino; Taliani, Sabrina; Cosconati, Sandro; Da Pozzo, Eleonora; Salerno, Silvia; Simorini, Francesca; Daniele, Simona; Giacomelli, Chiara; Marini, Anna Maria; La Motta, Concettina; Marinelli, Luciana; Cosimelli, Barbara; Novellino, Ettore; Greco, Giovanni; Da Settimo, Federico; Martini, Claudia

2015-08-13

As a continuation of our studies on 2-phenylindol-3-ylglyoxylamides as potent and selective translocator protein (TSPO) ligands, two subsets of novel derivatives, featuring hydrophilic group (OH, NH2, COOH) at the para-position of the pendent 2-phenyl ring (8-16) or different 2-aryl moieties, namely, 3-thienyl, p-biphenyl, 2-naphthyl (23-35), were synthesized and biologically evaluated, some of them showing Ki values in the subnanomolar range and the 2-naphthyl group performance being the best. The resulting SARs confirmed the key role played by interactions taking place between ligands and the lipophilic L1 pocket of the TSPO binding site. Docking simulations were performed on the most potent compound of the present series (29) exploiting the recently available 3D structures of TSPO bound to its standard ligand (PK11195). Our theoretical model was fully consistent with SARs of the newly investigated as well of the previously reported 2-phenylindol-3-ylglyoxylamide derivatives.

Synthesis and photochemistry of pH-sensitive GFP chromophore analogues

USDA-ARS?s Scientific Manuscript database

Nobel GFP chromophore analogues containing 2-thienyl-, 5-methyl-2-furyl-, 2-pyrryl, and 6-methyl-2-pyridyl-groups were synthesized, and their fluorescence spectra were recorded across pH range of 1 to 7. The GFP chromophores prevent photoisomerizaiton in acidic media and increase their fluorescent a...

Self-assembling of 2,3-phenyl/thienyl-substituted acrylic acids over polycrystalline gold

NASA Astrophysics Data System (ADS)

Csankó, K.; Kozma, G.; Valkai, L.; Kukovecz, Á.; Kónya, Z.; Sipos, P.; Pálinkó, I.

2013-07-01

Self-assembling layers were formed from sulfur-containing cinnamic acid analogues over polycrystalline Au surface. The horizontal organising forces were strong O-H⋯O and weaker C-H⋯S hydrogen bonds (the former interaction kept together the acid dimers serving as the fundamental unit, while the latter was crucial in the construction of the 2D layers), while the vertical organisation forces were provided by Au-S covalent bonds. Measurements by atomic force, scanning electron, infrared and Raman microscopies attested that the dimers were situated in a nearly perpendicular fashion to the Au surface providing a ˜30-40 nm thick organic "carpet" and out of this layer occasionally, peaks with height of ˜100-120 nm grew out. The outgrowth of these surface structures were most probably governed by the defects of the polycrystalline metal surface.

Synthesis, characterization and biological properties of thienyl derived triazole Schiff bases and their oxovanadium(IV) complexes.

PubMed

Chohan, Zahid H; Sumrra, Sajjad H

2012-04-01

A new series of biologically active thienyl derived triazole Schiff bases and their oxovanadium(IV) complexes have been synthesized and characterized on the basis of physical (m.p., magnetic susceptibility and conductivity), spectral (IR, ¹H and ¹³C NMR, electronic and mass spectrometry) and microanalytical data. All the Schiff base ligands and their oxovanadium(IV) complexes have been subjected to in vitro antibacterial activity against four Gram-negative (Escherichia coli, Shigella flexneri, Pseudomonas aeruginosa, Salmonella enterica serover typhi) and two Gram-positive (Staphylococcus aureus and Bacillus subtilis) bacterial strains and, for in vitro antifungal activity against Trichophyton longifucus, Candida albican, Aspergillus flavus, Microscopum canis, Fusarium solani and Candida glabrata. Brine shrimp bioassay was also carried out to check the cytotoxic nature of these compounds.

Crystal structures and intermolecular interactions of two novel antioxidant triazolyl-benzimidazole compounds

DOE Office of Scientific and Technical Information (OSTI.GOV)

Karayel, A., E-mail: matchlessjimmy@163.com, E-mail: yccaoh@hotmail.com; Özbey, S.; Ayhan-Kılcıgil, G.

2015-12-15

The crystal structures of 5-(2-(p-chlorophenylbenzimidazol-1-yl-methyl)-4-(3-fluorophenyl)-2, 4-dihydro-[1,2,4]-triazole-3-thione (G6C) and 5-(2-(p-chlorophenylbenzimidazol-1-yl-methyl)-4-(2-methylphenyl)-2, 4-dihydro-[1,2,4]-triazole-3-thione (G4C) have been determined by single-crystal X-ray diffraction. Benzimidazole ring systems in both molecules are planar. The triazole part is almost perpendicular to the phenyl and the benzimidazole parts of the molecules in order to avoid steric interactions between the rings. The crystal structures are stabilized by intermolecular hydrogen bonds between the amino group of the triazole and the nitrogen atom of benzimidazole of a neighboring molecule.

RATES OF SOLVOLYSIS OF SOME DEUTERATED 2-PHENYLETHYL p-TOLUENESULFONATES

DOE Office of Scientific and Technical Information (OSTI.GOV)

Saunders, W.H. Jr.; Asperger, S.; Edison, D.H.

1958-05-20

Rates of solvolysis of 2-phenylethyl (Ia), b 2/ (Ic) p-toluenesulfonates were determined in formic and in acetic acid. In formolysis Ia and Ic react at the same rate, but Ia reacts 17 plus or minus 2% faster than Ib. In acetolysis small effects are observed with both deuterated com. pounds: Ia is 3 plus or minus 1% faster than Ib and 4 plus or minus 3% faster than Ic. The formates and acetates produced in the solvolyses were converted to the corresponding 2phenylethanols II. Comparison of the infrared spectra of the products with those of synthetic mixture of IIb andmore » IIc revealed that ca. 45% phenyl migration had occurred in the formolysis and ca. 10% phenyl migration in acetolysis. These results suggest that phenyl participation predominates in formolysis, but is unimportant in acetolysis. The nature of the transition state in phenyl- participation reactions and the factors contributing to secondary deuterium isotope effects are discussed. (auth)« less

Supramolecular assembly of (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate, crystal structure, Hirshfeld surface analysis and DFT studies

NASA Astrophysics Data System (ADS)

Matos, Catiúcia R. M. O.; Vitorino, Letícia S.; de Oliveira, Pedro H. R.; de Souza, Maria Cecília B. V.; Cunha, Anna C.; Boechat, Fernanda da C. S.; Resende, Jackson A. L. C.; Carneiro, José Walkimar de M.; Ronconi, Célia M.

2016-09-01

A mixture of the E and Z isomers of ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate was synthesized and characterized by elemental analysis, attenuated total reflectance-Fourier transform infrared spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopy. The structure of the Z isomer was determined by single crystal X-ray diffraction, which revealed a three-dimensional supramolecular network governed by Csbnd H⋯N, Csbnd H⋯O, and Csbnd H⋯F hydrogen bonds and π⋯π stacking interactions. The combination of these interactions plays an important role in stabilizing the self-assembly process and the molecular conformation. Hirshfeld surface analysis indicated the roles of the noncovalent interactions in the crystal packing, which were quantified by fingerprint plots and DFT calculations.

Gas-phase reactions of phenyl radicals with aromatic molecules

DOE Office of Scientific and Technical Information (OSTI.GOV)

Fahr, A.; Stein, S.E.

1988-08-25

Relative rates of reactions of phenyl radicals with a series of aromatic and polycyclic aromatic compounds are reported. Most studies were done in static reactors at 450/degrees/C using diphenyl diketone (benzil) as the phenyl radical source. Reactions with the following molecules are reported: benzene, toluene, p-xylene, 1,3,5-trimethylbenzene, phenol, bromobenzene, naphthalene, biphenyl, anthracene, 9-methylanthracene, and triphenylene. For reactions with substituted benzenes, H abstraction is the dominant reaction. Relative rates of phenylation at different sites do not closely follow established trends for rates of radical attack. It is proposed that these deviations are primarily due to a dependence of the degree ofmore » reversibility on the specific site of phenylation. These studies also show that the rates of phenyl and H-atom migration around the ring in adduct radicals are slow relative to dissociation. Also, by use of these results to link literature rate data from high and low temperatures, a rate expression for H abstraction from p-xylene by phenyl of 10/sup 9.6/ exp(-4.4 kcal/RT) M/sup /minus/1/ s/sup /minus/1/ is derived.« less

On the behaviour of biradicaloid [P(μ-NTer)]2 towards Lewis acids and bases.

PubMed

Hinz, Alexander; Schulz, Axel; Villinger, Alexander

2016-05-07

The well-known diphosphadiazane-1,3-diyl [P(μ-NTer)]2 (Ter = 2,6-bis(2,4,6-trimethyl-phenyl)-phenyl) was treated with Lewis bases such as N-heterocyclic carbenes and Lewis acids e.g. gold(i) chloride complexes. In the reaction with the Lewis base, fragmentation of the P2N2 framework was observed, yielding a salt of the type [(NHC)2P](+)[(TerN)2P](-) in a clean reaction. The reaction of [P(μ-NTer)]2 with gold(i) chloride afforded 1 : 1 and 1 : 2 complexes. The dinuclear complex [(ClAu)2P(μ-NTer)2P] displays a bridging P atom between both gold centers, as has been observed for P based zwitterions.

3-(6-Methyl-2-pyrid­yl)-2-phenyl-3,4-dihydro-1,3,2-benzoxaza­phosphinine 2-oxide

PubMed Central

Surendra Babu, V. H. H.; Krishnaiah, M.; Anil Kumar, M.; Suresh Reddy, C.; Kant, Rajni

2009-01-01

In the title compound, C19H17N2O2P, the six-membered 1,3,2-oxaza­phosphinine ring adopts a boat conformation with the phosphoryl O atom in an equatorial position. The dihedral angle between the 6-methyl-2-pyridyl and phenyl groups is 75.5 (1)°. These substituents are trans to each other, and are oriented at angles of 57.2 (1) and 74.8 (1)°, respectively, to the benzene ring. The crystal structure is stabilized by intra- and inter­molecular hydrogen bonds. The phosphoryl O atom participates in inter­molecular C—H⋯O inter­actions with the neighbouring mol­ecules, forming centrosymmetric R 2 2(14) dimers. PMID:21578300

Synthesis, crystal structure analysis, spectral investigations, DFT computations, Biological activities and molecular docking of methyl(2E)-2-{[N-(2-formylphenyl)(4-methylbenzene) sulfonamido]methyl}-3-(4-fluorophenyl)prop-2-enoate, a potential bioactive agent

NASA Astrophysics Data System (ADS)

Murugavel, S.; Vetri Velan, V.; Kannan, Damodharan; Bakthadoss, Manickam

2016-03-01

The title compound methyl(2E)-2-{[N-(2-formylphenyl) (4-methylbenzene)sulfonamido]methyl}-3-(4-fluorophenyl) prop-2-enoate (MFMSF) has been synthesized and single crystals were grown by slow evaporation solution growth technique at room temperature. The grown crystals were characterized by FTIR, 1H NMR, 13C NMR, and single crystal X-ray diffraction. In the crystal, molecules are linked by intermolecular C-H…O hydrogen bonds forming a two-dimensional supramolecular network along [110] direction. The molecular geometry was also optimized using density functional theory (DFT/B3LYP) method with the 6-311G (d,p) basis set in ground state and compared with the experimental data. The entire vibrational assignments of wave numbers were made on the basis of potential energy distribution (PED) by VEDA 4 programme. Stability of the molecule arising from hyper conjugative interactions, charge delocalization has been analyzed using natural bond orbital (NBO) analysis. In addition, NLO, MEP, Mulliken, thermodynamic properties, HOMO and LUMO energy gap were theoretically predicted. The global chemical reactivity descriptors are calculated for MFMSF and used to predict their relative stability and reactivity. The antibacterial activity of the compound was also tested against various pathogens. The molecular docking studies concede that title compound may exhibit PBP-2X inhibitor activity.

Fluorine substitution and nonconventional OH...pi intramolecular bond: high-resolution UV spectroscopy and ab initio calculations of 2-(p-fluorophenyl)ethanol.

PubMed

Karaminkov, Rosen; Chervenkov, Sotir; Neusser, Hans J

2008-05-21

The para-fluorinated flexible neurotransmitter analogue 2-phenylethanol has been investigated by highly resolved resonance-enhanced two-photon ionisation two-colour UV laser spectroscopy with mass resolution and ab initio structural optimisations and energy calculations. Two stable conformations, gauche and anti, separated by a high potential barrier have been identified in the cold molecular beam by rotational analysis of the vibronic band structures. The theoretically predicted higher-lying conformations most likely relax to these two structures during the adiabatic expansion. The lowest-energy gauche conformer is stabilised by an intramolecular nonconventional OH...pi-type hydrogen bond between the terminal OH group of the side chain and the pi electrons of the phenyl ring. The good agreement between the experimental and theoretical results demonstrates that even the substitution with a strongly electronegative atom of 2-phenylethanol at the para position has no noticeable effect on the strength and orientation of the OH...pi bond.

High-temperature polyimides prepared from 2,2-bis-[(2-halo-4-aminophenoxy)-phenyl]hexafluoropropane

NASA Technical Reports Server (NTRS)

Jones, Robert J. (Inventor); Chang, Glenn E. C. (Inventor)

1984-01-01

There are provided the aromatic diamines 2,2-bis-[(2-halo-4-aminophenoxy)-phenyl]hexafluoropropane, where the attached ortho halogen is preferably chlorine, and 4,4'-bis(4-aminophenoxy)biphenyl, as novel monomers for polyimide polymerizations. The former, when reacted with 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, provides a polyimide having exceptional high-temperature performance. The latter diamine is a low-cost monomer for polyimide production.

Simple synthesis of P(Cbz-alt-TBT) and PCDTBT by combining direct arylation with suzuki polycondensation of heteroaryl chlorides.

PubMed

Lombeck, Florian; Matsidik, Rukiya; Komber, Hartmut; Sommer, Michael

2015-01-01

Direct arylation (DA) of 2-chlorothiophene and 2-chloro-3-hexylthiophene with 4,7-dibromo-2,1,3-benzothiadiazole is used to synthesize 4,7-bis(5-chloro-2-thienyl)-2,1,3-benzothiadiazole (TBTCl2) and 4,7-bis(5-chloro-4-hexyl-2-thienyl)-2,1,3-benzothiadiazole (DH-TBTCl2) in one step. Suitable conditions of the Suzuki polycondensations (SPC) of TBTCl2 and DH-TBTCl2 with the carbazole comonomer CbzPBE2 are established, furnishing PCDTBT and P(Cbz-alt-TBT) with high molecular weight and yield. Compared with control samples made from the corresponding dibromides, high-temperature NMR and UV-vis spectroscopy indicate similar properties for PCDTBT but an increased content of Cbz-Cbz homocouplings for P(Cbz-alt-TBT). © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Synthesis, spectroscopic, anticancer, antibacterial and antifungal studies of Ni(II) and Cu(II) complexes with hydrazine carboxamide, 2-[3-methyl-2-thienyl methylene

NASA Astrophysics Data System (ADS)

Chandra, Sulekh; Vandana; Kumar, Suresh

2015-01-01

Schiff's base ligand(L) hydrazine carboxamide, 2-[3-methyl-2-thienyl methylene] and its metal complexes have been synthesized and characterized by elemental analysis, molar conductance, various spectroscopic techniques such as electronic, IR, 1H NMR, mass, EPR. Molar conductance of complexes in DMF solution corresponds to non-electrolyte. Complexes have general composition [M(L)2X2], where M = Ni(II) and Cu(II), X = Cl-, NO3-, CH3COO- and ½SO42-. On the basis of above spectral studies, an octahedral geometry has been assigned for Ni(II) complexes and tetragonal geometry for Cu(II) complexes except [Cu(L)2SO4] which possesses five coordinated trigonal bipyramidal geometry. These metal complexes were also tested for their anticancer, antibacterial and antifungal activities to assess their inhibition potential. Anticancer activity of ligand and its metal complexes were evaluated using SRB fluorometric assay and Adriamycin (ADR) was applied as positive control. Schiff's base ligand and its metal complexes were screened for their antibacterial and antifungal activity against Escherichia coli, Bacillus cereus and Aspergillus niger, Aspergillus flavus, respectively. Kirby-Bauer single disk susceptibility test was used for antibacterial activity and well diffusion method for antifungal activity of the compounds on the used fungi.

Growth and characterization of new nonlinear optical 1-phenyl-3-(4-dimethylamino phenyl) prop-2-en-1-one (PDAC) single crystals

NASA Astrophysics Data System (ADS)

Ravindraswami, K.; Janardhana, K.; Gowda, Jayaprakash; Moolya, B. Narayana

2018-04-01

Non linear optical 1-phenyl-3-(4-dimethylamino phenyl) prop-2-en-1-one (PDAC) was synthesized using Claisen - Schmidt condensation method and studied for optical nonlinearity with an emphasis on structure-property relationship. The structural confirmation studies were carried out using 1H-NMR, FT-IR and single crystal XRD techniques. The nonlinear absorption and nonlinear refraction parameters in z-scan with nano second laser pulses were obtained by measuring the profile of propagated beam through the samples. The real and imaginary parts of third-order bulk susceptibility χ(3) were evaluated. Thermo gravimetric analysis is carried out to investigate the thermal stability.

Cholinesterases inhibition and molecular modeling studies of piperidyl-thienyl and 2-pyrazoline derivatives of chalcones.

PubMed

Shah, Muhammad Shakil; Khan, Shafi Ullah; Ejaz, Syeda Abida; Afridi, Saifullah; Rizvi, Syed Umar Farooq; Najam-Ul-Haq, Muhammad; Iqbal, Jamshed

2017-01-22

Super-activation of cholinesterases (acetylcholinesterase and butyrylcholinesterase) are linked to various neurological problems most precisely Alzheimer's disease (AD), which leads to senile dementia. Therefore, cholinesterases (AChE & BChE) inhibition are considered as a promising strategy for the treatment of Alzheimer's disease. FDA approved drugs for the treatment of AD, belong to a group of cholinesterase inhibitors. However, none of them is able to combat or completely abrogate the disease progression. Herein, we report a series of newly synthesized chalcone derivatives with anti-AD potential. For this purpose, a series of piperidyl-thienyl and 2-pyrazoline derivatives of chalcones were tested for their cholinesterases (AChE & BChE) inhibitory activity. All compounds were found as selective inhibitor of AChE. In piperidyl chalcones derivatives compound 1e having IC 50 of 0.16 ± 0.008 μM and 2m in 2-pyrazoline chalcones with IC 50 of 0.13 ± 0.006 μM, were found to be the most potent inhibitors of AChE, exhibiting ≈142 and ≈ 173-fold greater inhibitory potential compared to the reference inhibitor i.e., Neostigmine (IC 50  ± SEM = 22.2 ± 3.2 μM). Molecular docking studies of most potent inhibitors were carried out to investigate the binding interactions inside the active site. Molecular docking study revealed that potent compounds and co-crystalized ligand had same binding orientation within the active site of target enzyme. Most of these compounds are selective inhibitors of AChE with a potential use against progressive neurodegenerative disorder and age related problems. Copyright © 2016 Elsevier Inc. All rights reserved.

Solution-phase parallel syntheses of herbicidal 1-phenyl-2,4,5- imidazolidinetriones and 2-thioxo-4,5-imidazolidinediones.

PubMed

Li, Bin; Man, Ying; Bai, Li-Ping; Ji, Hai-Ying; Shi, Xue-Geng; Cui, Dong-Liang

2013-01-01

In order to find new herbicidally active compounds, a fifteen-member library, focusing on the variation of 3- position substituents of 2,4,5-imidazolidine-trione or 2-thioxo-4,5-imidazolidinedione, was designed and prepared in parallel by the reaction of various ureas or thioureas with oxalyl chloride using solution-phase technology. An interesting and, to the best of our knowledge, unprecedented finding is that a by-product of 1-phenyl-3-propylcarbodiimide was formed during the addition of oxalyl chloride into the solution of 1-phenyl-3-propylthiourea in the presence of triethylamine in dichloromethane. It has been shown that the herbicidal activity of 2,4,5-imidazolidinetriones is about the same as that of their analogous 2-thioxo-4,5-imidazolidinediones. Compound with propyl or isopropyl group at the 3- position of 2,4,5-imidazolidinetrione ring demonstrated good herbicidal activity. The most active compound, 1-(2-fluoro- 4-chloro-5-propargyloxy)-phenyl-3-propyl-2-thioxo-4,5-imidazolidinedione, gave 95% control of the growth of velvetleaf at 200 g/ha in the post-emergence test.

Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives.

PubMed

Tabatabai, Sayyed Abbas; Barghi Lashkari, Saoka; Zarrindast, Mohammad Reza; Gholibeikian, Mohammadreza; Shafiee, Abbas

2013-01-01

Benzodiazepines are useful drugs for treatment of sleep disorders, anxiety, seizure cases and skeletal muscle cramps. Some derivatives of 2-(2-Phenoxy) phenyl-1, 3, 4-oxadiazole were synthesized as benzodiazepine receptor agonists. Conformational analysis and superimposition of energy minima conformers of the compounds on estazolam, a known benzodiazepine agonist, reveal that the main proposed benzodiazepine pharmacophores were well matched. Anticonvulsant activity of the synthesized compounds, determined by pentylenetetrazole-induced lethal convulsion test, showed that the introduction of an amino substituent in position 5 of 1,3,4- oxadiazole ring generates compound 9 which has a respectable effect. The results are in agreement with SAR of benzodiazepine receptor ligands since the elimination of electronegative substituent in position 2 of phenoxy ring or position 4 of phenyl ring reduces the anticonvulsant activity.

Design, Synthesis and Anticonvulsant Activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole Derivatives

PubMed Central

Tabatabai, Sayyed Abbas; Barghi Lashkari, Saoka; Zarrindast, Mohammad Reza; Gholibeikian, Mohammadreza; Shafiee, Abbas

2013-01-01

Benzodiazepines are useful drugs for treatment of sleep disorders, anxiety, seizure cases and skeletal muscle cramps. Some derivatives of 2-(2-Phenoxy) phenyl-1, 3, 4-oxadiazole were synthesized as benzodiazepine receptor agonists. Conformational analysis and superimposition of energy minima conformers of the compounds on estazolam, a known benzodiazepine agonist, reveal that the main proposed benzodiazepine pharmacophores were well matched. Anticonvulsant activity of the synthesized compounds, determined by pentylenetetrazole-induced lethal convulsion test, showed that the introduction of an amino substituent in position 5 of 1,3,4- oxadiazole ring generates compound 9 which has a respectable effect. The results are in agreement with SAR of benzodiazepine receptor ligands since the elimination of electronegative substituent in position 2 of phenoxy ring or position 4 of phenyl ring reduces the anticonvulsant activity. PMID:24250678

(2E)-1-(2,6-Dichloro-3-fluoro-phen-yl)-3-phenyl-prop-2-en-1-one.

PubMed

Praveen, Aletti S; Yathirajan, Hemmige S; Narayana, Badiadka; Gerber, Thomas; Hosten, Eric; Betz, Richard

2012-04-01

In the title compound, C(15)H(9)Cl(2)FO, the F atom shows positional disorder over two positions, with site-occupancy factors of 0.747 (4) and 0.253 (4). The dihedral angle between the rings is 86.37 (10)°. In the crystal, C-H⋯O contacts connect the mol-ecules into chains along the c axis. The shortest inter-centroid distance between two aromatic systems is 3.6686 (12) Å and is apparent between the halogenated rings.

40 CFR 721.10130 - Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl...

Code of Federal Regulations, 2010 CFR

2010-07-01

...-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl]-, monosodium salt (generic). 721.10130 Section 721... Quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl]substituted]phenyl]-, monosodium... substance identified generically as quino[2,3-b]acridine-7,14-dione, 5,12-dihydro-ar-[4-[[2-(sulfooxy)ethyl...

Fast transient currents in Na,K-ATPase induced by ATP concentration jumps from the P3-[1-(3',5'-dimethoxyphenyl)-2-phenyl-2-oxo]ethyl ester of ATP.

PubMed Central

Sokolov, V S; Apell, H J; Corrie, J E; Trentham, D R

1998-01-01

Electrogenic ion transport by Na,K-ATPase was investigated by analysis of transient currents in a model system of protein-containing membrane fragments adsorbed to planar lipid bilayers. Sodium transport was triggered by ATP concentration jumps in which ATP was released from an inactive precursor by an intense near-UV light flash. The method has been used previously with the P3-1-(2-nitrophenyl)ethyl ester of ATP (NPE-caged ATP), from which the relatively slow rate of ATP release limits analysis of processes in the pump mechanism controlled by rate constants greater than 100 s(-1) at physiological pH. Here Na,K-ATPase was reinvestigated using the P3-[1-(3,5-dimethoxyphenyl)-2-phenyl-2-oxo]ethyl ester of ATP (DMB-caged ATP), which has an ATP release rate of >10(5) s(-1). Under otherwise identical conditions, photorelease of ATP from DMB-caged ATP showed faster kinetics of the transient current compared to that from NPE-caged ATP. With DMB-caged ATP, transient currents had rate profiles that were relatively insensitive to pH and the concentration of caged compound. Rate constants of ATP binding and of the E1 to E2 conformational change were compatible with earlier studies. Rate constants of enzyme phosphorylation and ADP-dependent dephosphorylation were 600 s(-1) and 1.5 x 10(6) M(-1) s(-1), respectively, at pH 7.2 and 22 degrees C. PMID:9591656

Temperature dependence of the Raman spectrum of 1-(4-chlorophenyl)-3-(2-thienyl)prop-2-en-1-one

NASA Astrophysics Data System (ADS)

de Toledo, T. A.; da Costa, R. C.; Al-Maqtari, H. M.; Jamalis, J.; Pizani, P. S.

2017-06-01

The heterocyclic chalcone containing thiophene ring 1-(4-chlorophenyl)-3-(2-thienyl)prop-2-en-1-one, C13H9ClOS was synthesized and investigated using experimental techniques such as nuclear magnetic resonance (1H and 13C NMR), Fourier transform infrared spectroscopy (FTIR) at room temperature, differential scanning calorimeter (DSC) from room temperature to 500 K and Raman scattering at the temperature range 10-413 K in order to study its structure and vibrational properties as well as stability and possible phase transition. Density functional theory (DFT) calculations were performed to determine the vibrational spectrum viewing to improve the knowledge of the material properties. A reasonable agreement was observed between theoretical and experimental Raman spectrum taken at 10 K since anharmonic effects of the molecular motion is reduced at low temperatures, leading to a more comprehensive assignment of the vibrational modes. Increasing the temperature up to 393 K, was observed the typical phonon anharmonicity behavior associated to changes in the Raman line intensities, line-widths and red-shift, in special in the external mode region, whereas the internal modes region remains almost unchanged due its strong chemical bonds. Furthermore, C13H9ClOS goes to melting phase transition in the temperature range 393-403 K and then sublimates in the temperature range 403-413 K. This is denounced by the disappearance of the external modes and the absence of internal modes in the Raman spectra, in accordance with DSC curve. The enthalpy (ΔH) obtained from the integration of the endothermic peak in DSC curve centered at 397 K is founded to be 121.5 J/g.

Comparative analysis of 1-phenyl-2-propanone (P2P), an amphetamine-type stimulant precursor, using stable isotope ratio mass spectrometry: presented in part as a poster at the 2nd meeting of the Joint European Stable Isotope User Meeting (JESIUM), Giens, France, September 2008.

PubMed

Schneiders, S; Holdermann, T; Dahlenburg, R

2009-06-01

The isotope ratios of amphetamine type stimulants (ATS) depend as well on the precursor as the synthetic pathway. For clandestine production of amphetamine and methamphetamine, 1-phenyl-2-propanone (P2P, benzylmethylketone) is a commonly used precursor. Our aim was to determine the variation of the isotope ratios within precursor samples of one manufacturer and to compare seized samples of unknown sources to these values. delta13C(V-PDB), delta2H(V-SMOW) and delta118O(V-SMOW) isotope ratios were determined using elemental analysis (EA) and gas chromatography (GC) coupled toan isotope ratio mass spectrometer (IRMS). The comparison of all seized samples to the data of the samples of one manufacturer revealed considerable differences. The results show that IRMS provides a high potential in differentiating between precursors from different manufacturers for the clandestine production of ATS and identifying corresponding sources.

A novel 4-phenyl amino thiourea derivative designed for real-time ratiometric-colorimetric detection of toxic Pb2.

PubMed

Guang, Yi S; Ren, Xia; Zhao, Shuang; Yan, Quan Z; Zhao, Gang; Xu, Yao H

2018-05-12

The objective of this study was to develop a ratiometric and colorimetric organic sensor for Pb 2+ detection in environmental samples. A new probe 4-phenyl amino thiourea (PAT) was designed and synthesized using hydrazine hydrate and phenyl isothiocyanate as raw materials. After its structure was characterized and confirmed, its UV-vis spectral property was investigated in detail. PAT possesses a specifically real-time, ratiometric and colorimetric response to Pb 2+ in dimethyl formamide (DMF)/H 2 O (v/v = 9:1, pH = 7.0) within 18.0 s. There was little interference in the presence of some other common metal ions, such as Fe 3+ , Cd 2+ , Zn 2+ , Mg 2+ , Cr 3+ , Ca 2+ , Ba 2+ , Sn 2+ , Na + , Mn 2+ , Hg 2+ , and Pb 2+ . Under the optimized conditions (DMF/H 2 O with v/v of 9:1, c PAT = 1.0 × 10 -3 mol·L -1 , pH = 7.0), the present sensor PAT was successfully applied for Pb 2+ determination in environmental water samples with satisfied recoveries (83.0%-106.0%) and analytical precision (≤7.2%). The recognition mechanism was confirmed to form a stable 1:1 six-member ring complex between the target dye and Pb 2+ with a coordination constant of 4.96 × 10 4 .

p -Carborane Conjugation in Radical Anions of Cage–Cage and Cage–Phenyl Compounds

DOE PAGES

Cook, Andrew R.; Valášek, Michal; Funston, Alison M.; ...

2017-12-14

Optical electron transfer (intervalence) transitions in radical anions of p-carborane oligomers attest to delocalization of electrons between two p-carboranes cages or a p-carborane and a phenyl ring. Oligomers of the 12 vertex p-carborane (C 2B 10H 12) cage, [12], with up to 3 cages were synthesized, as well as p-carboranes with one or two trimethylsilylphenyl groups, [6], attached to the carbon termini. Pulse radiolysis in tetrahydrofuran produced radical anions, determined redox potentials by equilibria and measured their absorption spectra. Density functional theory computations provided critical insight into the optical electron transfer bands and electron delocalization. One case, [6–12–6], showed bothmore » Robin–Day class II and III transitions. The class III transition resulted from a fully delocalized excess electron across both benzene rings and the central p-carborane, with an electronic coupling H ab = 0.46 eV between the cage and either benzene. This unprecedented finding shows that p-carborane bridges are not simply electron withdrawing insulators. In other cases with more than ~1/2 of the excess electron localized on a [12], large cage distortions were triggered, producing a partially open cage with a nido-like structure. This resulted in class II transitions with similar Hab but massive reorganization energies. The computations also predicted delocalization in radical cations, but complexities in cation formation allowed only tentative experimental support of the predictions. Thus, the results with anions provide clear evidence for carborane conjugation that might be exploited in molecular wire materials, which are classically composed of all π-conjugated molecules.« less

p -Carborane Conjugation in Radical Anions of Cage–Cage and Cage–Phenyl Compounds

DOE Office of Scientific and Technical Information (OSTI.GOV)

Cook, Andrew R.; Valášek, Michal; Funston, Alison M.

Optical electron transfer (intervalence) transitions in radical anions of p-carborane oligomers attest to delocalization of electrons between two p-carboranes cages or a p-carborane and a phenyl ring. Oligomers of the 12 vertex p-carborane (C 2B 10H 12) cage, [12], with up to 3 cages were synthesized, as well as p-carboranes with one or two trimethylsilylphenyl groups, [6], attached to the carbon termini. Pulse radiolysis in tetrahydrofuran produced radical anions, determined redox potentials by equilibria and measured their absorption spectra. Density functional theory computations provided critical insight into the optical electron transfer bands and electron delocalization. One case, [6–12–6], showed bothmore » Robin–Day class II and III transitions. The class III transition resulted from a fully delocalized excess electron across both benzene rings and the central p-carborane, with an electronic coupling H ab = 0.46 eV between the cage and either benzene. This unprecedented finding shows that p-carborane bridges are not simply electron withdrawing insulators. In other cases with more than ~1/2 of the excess electron localized on a [12], large cage distortions were triggered, producing a partially open cage with a nido-like structure. This resulted in class II transitions with similar Hab but massive reorganization energies. The computations also predicted delocalization in radical cations, but complexities in cation formation allowed only tentative experimental support of the predictions. Thus, the results with anions provide clear evidence for carborane conjugation that might be exploited in molecular wire materials, which are classically composed of all π-conjugated molecules.« less

Effect of solvent additives and P3HT on PDTSTTz/PCBM-based bulk heterojunction solar cells

NASA Astrophysics Data System (ADS)

Ergete, Assegid; Sabir, Fedlu K.; Li, Yongfang; Yohannes, Teketel

2015-01-01

In this investigation, photovoltaic (PV) parameters improvements in poly[2,6-(4,4‧-bis(2-ethylhexyl)dithieno[3,2-b:2‧,3‧-d]silole)-alt-5,5‧-(3,6-bis[4-(2-ethylhexyl)thienyl-2-yl]-s-tetrazine] and fullerene derivative [6,6]-phenyl-C61-butyric acid methyl ester (PDTSTTz:PCBM) blend were made through solvent additives and secondary donor addition. Short carbon chain solvent additives such as iodomethane (IMe), iodoethane (IEt), iodobutane (IBu), and diiodomethane (DIMe) were used. The results have shown that the short circuit current density (Jsc), as well as power conversion efficiency (PCE) of PDTSTTz:PCBM blend cell increased with the increase in length of carbon chains of the additives. IBu, with relatively the longest carbon chain, has better performance-improving impact than IMe (with the shortest carbon chain). The same trend was observed for fill factor. The other PV parameter, open circuit voltages (Voc), did not show significant change following these solvent additives. The effect of a secondary (additional) donor on the PDTSTTz/PCBM system was investigated by adding different proportions of poly(3-hexylthiophene-2,5-diyl) (P3HT). Because P3HT (secondary donor) and PDTSTTz (hosting donor) complement each other in light absorption, the PDTSTTz/PCBM system containing an optimum proportion of P3HT could provide a wider range of light absorption, and as a result it exhibited a higher short circuit current (11.08 mA/cm2) and then a PCE of 2.42%.

3-Methylthio-4-phenyl-5-phenylamino-1,2,4-triazole hexabromotellurate:X-ray and computational study

NASA Astrophysics Data System (ADS)

Fizer, Maksym; Slivka, Mikhailo; Mariychuk, Ruslan; Baumer, Vjacheslav; Lendel, Vasil

2018-06-01

The structure of a newly synthesized 3-methylthio-4-phenyl-5-phenylamino-1,2,4-triazole 1 and its hexabromotellurate salt 2 was investigated. The X-ray diffraction study of 2 gives the insight on the different interaction types in the crystal. The DFT calculations were used for the comprehensive study of the intramolecular and intermolecular forces that are present in the title 3-methylthio-4-phenyl-5-phenylamino-1,2,4-triazole hexabromotellurate. The presence of three different aromatic moieties in the investigated compounds cause π-π stacking interactions which were studied through the Hirshfeld surface analysis and with the discrimination of weak interaction types by filling color to a reduced density gradient (RDG) function isosurface. The RDG in the crystalline state was calculated upon experimental molecular geometry by partitions of the crystal to QM part that was calculated at M06-L/6-311G(d,p) level, and the semi-empirical QM part that was modeled with the PM7 method in QM/MM-like manner. The reactivity of 3-methylthio-4-phenyl-5-phenylamino-1,2,4-triazole and its protonated form was also discussed in terms of conceptual DFT theory and it shows the tendency of sulfur to be the most active center in an electrophilic and radical attack, whereas the site for nucleophilic substitution is medium dependent and not an unequivocal. NICS(1) index was used for the analysis of aromaticity of three different cyclic moieties. The present study insights the changes in the structure of a polyfunctional substituted triazole upon its protonation and explains these changes with the analysis of weak interactions.

Identification of [4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)-2-pyrimidinyl] amines and ethers as potent and selective cyclooxygenase-2 inhibitors.

PubMed

Swarbrick, Martin E; Beswick, Paul J; Gleave, Robert J; Green, Richard H; Bingham, Sharon; Bountra, Chas; Carter, Malcolm C; Chambers, Laura J; Chessell, Iain P; Clayton, Nick M; Collins, Sue D; Corfield, John A; Hartley, C David; Kleanthous, Savvas; Lambeth, Paul F; Lucas, Fiona S; Mathews, Neil; Naylor, Alan; Page, Lee W; Payne, Jeremy J; Pegg, Neil A; Price, Helen S; Skidmore, John; Stevens, Alexander J; Stocker, Richard; Stratton, Sharon C; Stuart, Alastair J; Wiseman, Joanne O

2009-08-01

A novel series of [4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)-2-pyrimidine-based cyclooxygenase-2 (COX-2) inhibitors, which have a different arrangement of substituents compared to the more common 1,2-diarylheterocycle based molecules, have been discovered. For example, 2-(butyloxy)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine (47), a member of the 2-pyrimidinyl ether series, has been shown to be a potent and selective inhibitor with a favourable pharmacokinetic profile, high brain penetration and good efficacy in rat models of hypersensitivity.

Discovery of (1R,2S)-2-{[(2,4-Dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (E2006): A Potent and Efficacious Oral Orexin Receptor Antagonist.

PubMed

Yoshida, Yu; Naoe, Yoshimitsu; Terauchi, Taro; Ozaki, Fumihiro; Doko, Takashi; Takemura, Ayumi; Tanaka, Toshiaki; Sorimachi, Keiichi; Beuckmann, Carsten T; Suzuki, Michiyuki; Ueno, Takashi; Ozaki, Shunsuke; Yonaga, Masahiro

2015-06-11

The orexin/hypocretin receptors are a family of G protein-coupled receptors and consist of orexin-1 (OX1) and orexin-2 (OX2) receptor subtypes. Orexin receptors are expressed throughout the central nervous system and are involved in the regulation of the sleep/wake cycle. Because modulation of these receptors constitutes a promising target for novel treatments of disorders associated with the control of sleep and wakefulness, such as insomnia, the development of orexin receptor antagonists has emerged as an important focus in drug discovery research. Here, we report the design, synthesis, characterization, and structure-activity relationships (SARs) of novel orexin receptor antagonists. Various modifications made to the core structure of a previously developed compound (-)-5, the lead molecule, resulted in compounds with improved chemical and pharmacological profiles. The investigation afforded a potential therapeutic agent, (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (E2006), an orally active, potent orexin antagonist. The efficacy was demonstrated in mice in an in vivo study by using sleep parameter measurements.

The role of polymer dots on efficiency enhancement of organic solar cells: Improving charge transport property

NASA Astrophysics Data System (ADS)

Li, Jinfeng; Zhang, Xinyuan; Liu, Chunyu; Li, Zhiqi; He, Yeyuan; Zhang, Zhihui; Shen, Liang; Guo, Wenbin; Ruan, Shengping

2017-07-01

In this work, poly(9,9-dioctylfluorene)-co-(4,7-di-2-thienyl-2,1,3-benzothiadiazole) (PF-5DTBT) and copolymer poly(styrene-co-maleic anhydride) (PSMA) dots were prepared as additive for active layer doping to enhance the power conversion efficiency (PCE) of organic solar cells (OSCs), which based on poly[N-9″-hepta-decanyl-2,7-carbazole-alt-5,5-(4‧,7‧-di-2-thienyl-2‧,1‧,3‧-benzothiadiazole) (PCDTBT) and [6,6]-phenyl C71 butyric acid methyl-ester (PC71BM). A high efficiency of 7.40% was achieved due to increase of short-circuit current (Jsc) and fill factor (FF). The operation mechanism of OSCs doping with polymer dots was investigated, which demonstrated that the efficiency enhancement ascribes to improvement of electrical properties, such as exciton generation, exction dissociation, charge transport, and charge collection.

Crystal structures of five 1-alkyl-4-aryl-1,2,4-triazol-1-ium halide salts.

PubMed

Guino-O, Marites A; Talbot, Meghan O; Slitts, Michael M; Pham, Theresa N; Audi, Maya C; Janzen, Daron E

2015-06-01

The asymmetric units for the salts 4-(4-fluoro-phen-yl)-1-isopropyl-1,2,4-triazol-1-ium iodide, C11H13FN3 (+)·I(-), (1), 1-isopropyl-4-(4-methyl-phen-yl)-1,2,4-triazol-1-ium iodide, C12H16N3 (+)·I(-), (2), 1-isopropyl-4-phenyl-1,2,4-triazol-1-ium iodide, C11H14N3 (+)·I(-), (3), and 1-methyl-4-phenyl-1,2,4-triazol-1-ium iodide, C9H10N3 (+)·I(-), (4), contain one cation and one iodide ion, whereas in 1-benzyl-4-phenyl-1,2,4-triazol-1-ium bromide monohydrate, C15H14N3 (+)·Br(-)·H2O, (5), there is an additional single water mol-ecule. There is a predominant C-H⋯X(halide) inter-action for all salts, resulting in a two-dimensional extended sheet network between the triazolium cation and the halide ions. For salts with para-substitution on the aryl ring, there is an additional π-anion inter-action between a triazolium carbon and iodide displayed by the layers. For salts without the para-substitution on the aryl ring, the π-π inter-actions are between the triazolium and aryl rings. The melting points of these salts agree with the predicted substituent inductive effects.

Synthesis, characterization, antimicrobial screening and computational studies of 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one

NASA Astrophysics Data System (ADS)

Obasi, L. N.; Kaior, G. U.; Rhyman, L.; Alswaidan, Ibrahim A.; Fun, Hoong-Kun; Ramasami, P.

2016-09-01

The Schiff base, 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (TPMC/AAP) was synthesized by the condensation of 4-aminoantipyrine (4-amino-1,5-dimethyl-2-phenylpyrazole-3-one) and trans-para-methoxycinnamaldehyde (trans-3,4-methoxyphenyl-2-propenal) in dry methanol at 75 °C. The compound was characterized using elemental microanalysis, IR, NMR, UV spectroscopies and single-crystal X-ray crystallography. The X-ray structure determination shows that the Schiff base, (TPMC/AAP) is orthorhombic with the Pbca space group. The anti-microbial screening of the compound was carried out with Escherichia coli, Bacillus subtillis, Staphylococcus aureus, Pseudemonas aeruginosa, Candida albicans and Aspergillus niger using agar well diffusion method. The Schiff base possesses significant antimicrobial activity. The minimum inhibitory concentration (MIC) of the compound was also determined and the activity was compared with that of conventional drugs ciprofloxacin and ketoconazole. The compound (TPMC/AAP) showed varying activity against the cultured bacteria and fungi used. To complement the experimental data, density functional theory (DFT) was used to have deeper understanding into the molecular parameters and infrared spectra of the compound.

Cyclometalated 6-phenyl-2,2'-bipyridyl (CNN) platinum(II) acetylide complexes: structure, electrochemistry, photophysics, and oxidative- and reductive-quenching studies.

PubMed

Schneider, Jacob; Du, Pingwu; Jarosz, Paul; Lazarides, Theodore; Wang, Xiaoyong; Brennessel, William W; Eisenberg, Richard

2009-05-18

Three cyclometalated 6-phenyl-4-(p-R-phenyl)-2,2'-bipyridyl (CNN-Ph-R) Pt(II) acetylide complexes, Pt(CNN-Ph-R)(CCPh), where R = Me (1), COOMe (2), and P(O)(OEt)(2) (3), have been synthesized and studied. Compounds 1 and 3 have been structurally characterized by single crystal X-ray crystallography and are found to exhibit distorted square planar geometries about the Pt(II) ions. The electrochemical properties of the compounds, as determined by cyclic voltammetry, have also been examined. Complexes 1-3 are brightly emissive in fluid CH(2)Cl(2) solution and in the solid state with lambda(em)(max) of ca. 600 nm and lifetimes on the order of ca. 500 ns in fluid solution. The emissions are assigned to a (3)MLCT transition. The complexes undergo oxidative quenching by MV(2+) with quenching rates near the diffusion-controlled limit (k(q) approximately 1.4 x 10(10) M(-1) s(-1)) in CH(2)Cl(2) solution. Reductive-quenching experiments of complexes 1-3 by the amine donors N,N,N',N'-tetramethylphenylenediamine (TMPD), phenothiazine (PTZ), and N,N,N',N'-tetramethylbenzidine (TMB) follow Stern-Volmer behavior, with very fast quenching rates on the order of 10(9)-10(10) M(-1) s(-1) in CH(2)Cl(2) solution. When the complexes are employed as the sensitizer in multiple component systems containing MV(2+), TEOA, and colloidal Pt in aqueous media, approximately one turnover of H(2) (TN vs mol of chromophore) is produced per hour upon irradiation with lambda > 410 nm but only after at least a 2 h induction period.

Dichlorido{[2-(diphenyl­phosphino)phenyl­imino­meth­yl]ferrocene-κ2 N,P}palladium(II) dichloro­methane hemi­solvate

PubMed Central

Liu, Huanyu; Shen, Dongsheng

2009-01-01

There are two independent PdII complex mol­ecules in the asymmetric unit of the title compound, [PdCl2{Fe(C5H5)(C24H19NP)}]·0.5CH2Cl2. One ferrocenyl ring of one complex mol­ecule is disordered over two sites with half-occupancy for each component. Both PdII cations adopt a distorted square-planar coordination geometry with a bidentate [2-(diphenyl­phosphino)phenyl­imino­meth­yl]ferrocene ligand and two chloride anions. PMID:21581545

Biting deterrence and insecticidal activity of hydrazide-hydrazones and their corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles against Aedes aegypti.

PubMed

Tabanca, Nurhayat; Ali, Abbas; Bernier, Ulrich R; Khan, Ikhlas A; Kocyigit-Kaymakcioglu, Bedia; Oruç-Emre, Emine E; Unsalan, Seda; Rollas, Sevim

2013-06-01

Taking into account the improvement in insecticidal activity by the inclusion of fluorine in the hydrazone moiety, the authors synthesized new 4-fluorobenzoic acid hydrazides and 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles, substituting a phenyl group or a heteroaryl ring carrying one or two atoms of F, Cl and Br, and investigated their biting deterrent and larvicidal activities against Aedes aegypti for the first time. The compound 3-acetyl-5-(4-fluorophenyl)-2-[4-(dimethylamino)phenyl]-2,3-dihydro-1,3,4-oxadiazole (17) produced the highest biting deterrent activity (BDI = 1.025) against Ae. Aegypti, followed by 4-fluorobenzoic acid [(phenyl)methylene] hydrazide (1). These activity results were similar to those of N,N-diethyl-meta-toluamide (DEET), which showed a proportion not biting of 0.8-0.92. When compounds 1 and 17 were tested on cloth worn on human volunteers, compound 1 was not repellent for some volunteers until present in excess of 500 nmol cm(-2) , while compound 17 was not repellent at the highest concentration tested (1685 nmol cm(-2) ). In the larvicidal screening bioassays, only compounds 10, 11, 12 and 17 showed 100% mortality at the highest screening dose of 100 ppm against Ae. aegypti larvae. Compounds 11 and 12 with LD50 values of 24.1 and 30.9 ppm showed significantly higher mortality than 10 (80.3 ppm) and 17 (58.7 ppm) at 24-h post-treatment. The insecticidal and biting deterrent activities were correlated with the presence of a halogen atom on the phenyl or heteroaryl substituent of the hydrazone moiety. © 2012 Society of Chemical Industry.

Structure elucidation of the designer drug N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-3-(4-fluorophenyl)-pyrazole-5-carboxamide and the relevance of predicted (13) C NMR shifts - a case study.

PubMed

Girreser, Ulrich; Rösner, Peter; Vasilev, Andrej

2016-07-01

The detailed structure elucidation process of the new cannabimimetic designer drug, N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-3-(4-fluorophenyl)-pyrazole-5-carboxamide, with a highly substituted pyrazole skeleton, using nuclear magnetic resonance (NMR) spectroscopic and mass spectrometric (MS) techniques is described. After a first analysis of the NMR spectra and comparison with 48 possible pyrazole and imidazole structures, a subset of six positional isomeric pyrazoles and six imidazoles remained conceivable. Four substituents of the heterocyclic skeleton were identified: a proton bound to a pyrazole ring carbon atom; a 5-fluoropentyl group; a 4-fluorophenyl substituent; and a carbamoyl group, which is N-substituted with a methyl residue carrying a tert.-butyl and a carbamoyl substituent. The 5-fluoropentyl residue is situated at the nitrogen ring atom. Additional NMR experiments like the (1) H,(13) C HMBC were performed, but due to the small number of signals based on long-range couplings, the comparison of predicted and observed (13) C chemical shifts became necessary. The open access Internet shift prediction programs NMRDB, NMRSHIFTDB2, and CSEARCH were employed for the prediction of (13) C shift values which allowed an efficient and unambiguous structure determination. For the identified N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-3-(4-fluorophenyl)-pyrazole-5-carboxamide, the best agreement between predicted (13) C shifts and the observed chemical shifts and long-range couplings for the pyrazole ring carbon atoms, with a standard error of about 2 ppm, was found with each of the predictions. For the comparison of measured and predicted chemical shifts model compounds with simple substituents proved helpful. The identified compound is a homologue of AZ-037 which is offered by Internet suppliers. Copyright © 2015 John Wiley & Sons, Ltd. Copyright © 2015 John Wiley & Sons, Ltd.

Pharmacological studies on the TXA2 synthetase inhibitor (E)-3-[p-(1H-imidazol-1-ylmethyl)phenyl]-2-propenoic acid (OKY-046).

PubMed

Hiraku, S; Taniguchi, K; Wakitani, K; Omawari, N; Kira, H; Miyamoto, T; Okegawa, T; Kawasaki, A; Ujiie, A

1986-07-01

The effects of (E)-3-[p-(1H-imidazol-1-ylmethyl)phenyl]-2-propenoic acid (OKY-046) on thromboxane A2 (TXA2) synthetase in vitro and on experimental animal models of sudden death and cerebral infarction were studied. IC50 values of OKY-046 for the TXA2 synthetase of human, rabbit, dog and guinea pig washed platelets were 0.004, 0.004, 0.26 and 2.4 microM, respectively. OKY-046 at concentrations up to 1 mM, however, did not inhibit prostacyclin (PGI2) synthetase from bovine aorta microsomes or cyclooxygenase and PGE2 isomerase from sheep seminal vesicle microsomes. Similarly, platelet 12-lipoxygenase was not affected by OKY-046. Evidence for a re-direction of arachidonate metabolism from thromboxane synthesis toward PGI2 synthesis was obtained using rat peritoneal cells. Namely, OKY-046 increased PGI2 production accompanied by an inhibition of TXA2 production at a concentration of more than 1 microM. OKY-046 at a dose of 0.1 mg/kg (i.v.) in dogs inhibited the aortic and mesenteric arterial contraction of rabbit induced by the addition of arachidonate to extracorporated blood of the dogs. OKY-046 at a dose of 0.3 mg/kg (i.v.) prevented the arachidonate-induced sudden death and also decreased the incidence of cerebral infarction induced by injection of arachidonate into the internal carotid artery in rabbits. Aspirin also decreased the incidence of cerebral infarction at a dose of 30 mg/kg (i.v.). These results suggest that OKY-046 may be valuable for the treatment of cerebrovascular and cardiovascular diseases associated with vasoconstriction and thrombosis due to TXA2.

Substituent effect in spin-crossover behavior of iron(II)-Ar-pybox complexes (Ar-pybox = 4-aryl-2,6-bis(oxazolin-2-yl)pyridine)

NASA Astrophysics Data System (ADS)

Kimura, Akifumi; Ishida, Takayuki

2018-01-01

Spin-crossover (SCO) is a reversible transition between low-spin (LS) and high-spin (HS) states by external stimuli like heat. The SCO behavior of [Fe(Ar-pybox)2](ClO4)2 was investigated, where Ar-pybox stands for 4-aryl-2,6-bis(oxazolin-2-yl)pyridine with Ar = 4-pyridyl (4Py), 3-thienyl (3Th), and phenyl (Ph). They were characterized by means of single-crystal X-ray diffraction study, being consistent with the results of the magnetic measurements. The SCO temperatures (T1/2) in the polycrystalline state were determined to be 360 and 230 K for Ar = 4Py and Ph, respectively. The 3Th derivative possessed a HS state in all the temperature range. The solution susceptometry was also performed to purge intermolecular interaction and rigid crystal lattice effects, affording T1/2 = 310, 240, and 240 K for Ar = 4Py, 3Th, and Ph, respectively, in acetone. The substituent effect analysis using the Hammett substituent constant (σp) clarified that electron-withdrawing groups raise T1/2. A plausible model describing the substituent effect on T1/2 is proposed based on d-π interaction. The present result is regarded as a successful example of crystal field engineering.

Development of 1-aryl-3-furanyl/thienyl-imidazopyridine templates for inhibitors against hypoxia inducible factor (HIF)-1 transcriptional activity.

PubMed

Fuse, Shinichiro; Ohuchi, Toshiaki; Asawa, Yasunobu; Sato, Shinichi; Nakamura, Hiroyuki

2016-12-15

1,3-Disubstituted-imidazopyridines were designed for developing inhibitors against HIF-1 transcriptional activity. Designed compounds were rapidly synthesized from a key aromatic scaffold via microwave-assisted Suzuki-Miyaura coupling/CH direct arylation sequence. Evaluation of ability to inhibit the hypoxia induced transcriptional activity of HIF-1 revealed that the compound 2i and 3a retained the same level of the inhibitory activity comparing with that of known inhibitor, YC-1 (1). Identified, readily accessible 1-aryl-3-furanyl/thienyl-imidazopyridine templates should be useful for future drug development. Copyright © 2016 Elsevier Ltd. All rights reserved.

40 CFR 721.5276 - 2-Naphthalenol, heptyl-1-[[(4-phenylazo)phenyl]azo]-, ar′,ar″-Me derivs.

Code of Federal Regulations, 2010 CFR

2010-07-01

...-phenylazo)phenyl]azo]-, ar′,ar″-Me derivs. (a) Chemical substance and significant new uses subject to...]-, ar′,ar″-Me derivs (PMN P-95-538) is subject to reporting under this section for the significant new...

Some actions of substituted choline phenyl ethers, particularly of choline 2:6-xylyl ether

PubMed Central

Edge, N. D.; Mason, D. F. J.; Wyllie, J. H.

1957-01-01

Marked nicotine-like stimulant properties are possessed by choline phenyl ether and choline o-tolyl ether, and to a decreasing extent by choline 2:6-xylyl ether and choline 2:4:6-mesityl ether. The compounds all show neuromuscular blocking properties, which are of short duration and pass from mainly decamethonium-like to mainly curare-like as more methyl groups are added to the phenyl nucleus. This series of compounds also possesses muscarinic, weak anti-adrenaline and vasodilator properties, as well as long-lasting local anaesthetic effects in the two compounds tested by intradermal injection. PMID:13460236

VU6010608, a Novel mGlu7 NAM from a Series of N-(2-(1H-1,2,4-Triazol-1-yl)-5-(trifluoromethoxy)phenyl)benzamides.

PubMed

Reed, Carson W; McGowan, Kevin M; Spearing, Paul K; Stansley, Branden J; Roenfanz, Hanna F; Engers, Darren W; Rodriguez, Alice L; Engelberg, Eileen M; Luscombe, Vincent B; Loch, Matthew T; Remke, Daniel H; Rook, Jerri M; Blobaum, Anna L; Conn, P Jeffrey; Niswender, Colleen M; Lindsley, Craig W

2017-12-14

Herein, we report the structure-activity relationships within a series of mGlu 7 NAMs based on an N -(2-(1 H -1,2,4-triazol-1-yl)-5-(trifluoromethoxy)phenyl)benzamide core with excellent CNS penetration ( K p 1.9-5.8 and K p,uu 0.4-1.4). Analogues in this series displayed steep SAR. Of these, VU6010608 ( 11a ) emerged with robust efficacy in blocking high frequency stimulated long-term potentiation in electrophysiology studies.

40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

Code of Federal Regulations, 2013 CFR

2013-07-01

... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN P-00...

40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN P-00...

40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN P-00...

40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN P-00...

40 CFR 721.9538 - Lithium salt of sulfophenyl azo phenyl azo disulfostilbene (generic).

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Lithium salt of sulfophenyl azo phenyl... Significant New Uses for Specific Chemical Substances § 721.9538 Lithium salt of sulfophenyl azo phenyl azo... substance identified generically as lithium salt of sulfophenyl azo phenyl azo disulfostilbene (PMN P-00...

Photoluminescence spectral reliance on aggregation order of 1,1-Bis(2'-thienyl)-2,3,4,5-tetraphenylsilole.

PubMed

Chen, Junwu; Xu, Bin; Yang, Kaixia; Cao, Yong; Sung, Herman H Y; Williams, Ian D; Tang, Ben Zhong

2005-09-15

1,1-Bis(2'-thienyl)-2,3,4,5-tetraphenylsilole (1) was prepared and characterized crystallographically. Silole 1 exhibited aggregation-induced emission (AIE) behavior like other 2,3,4,5-tetraphenylsiloles. Unexpectedly, aggregates formed in water/acetone (6:4 by volume) mixture emitted a blue light that peaked at 474 nm, while aggregates formed in the mixtures with higher water fractions emitted green light that peaked at 500 nm. Transmission electron microscopy demonstrated that the aggregates formed in the mixture with water fraction of 60% were single crystals, while aggregates that formed in the mixture with water fraction of 90% were irregular and poorly ordered particles. The unusual PL spectral reliance on aggregation order was further confirmed by PL emissions of macroscopic crystal powders and amorphous powders of the silole in the dry state. PL spectral blue shifting was observed upon aging of the poorly ordered aggregates formed in mixtures with water fractions of 70-90%, and they finally exhibited the same blue emission as the crystalline aggregates. The as-deposited thin solid film was amorphous and it could be transformed to a transparent crystalline film upon treatment in the vapor of an ethanol/water (1:1 by volume) mixture, along with PL spectral blue shifting due to changing of aggregation order. It was also found that the crystalline film showed a blue-shifted absorption spectrum relative to the amorphous film and the shift of the absorption edge of the spectra could match that of corresponding PL spectra. The FT-IR spectrum of crystal powders of 1 displayed more vibration modes compared with that of amorphous powders, suggesting the existence of different pi-overlaps or different molecular conformations. The crystals of 1-methyl-1,2,3,4,5-pentaphenylsilole and hexaphenylsilole also showed blue-shifted PL emissions of their amorphous solids, with a comparable PL spectral shift of 1. Developing of a silole solution on a TLC plate readily brought

Influencing the electronic interaction in diferrocenyl-1-phenyl-1H-pyrroles.

PubMed

Hildebrandt, Alexander; Lang, Heinrich

2011-11-28

Functionalised diferrocenyl-1-phenyl-1H-pyrroles were synthesised using Negishi C,C cross-coupling reactions. The influence of different substituents at the phenyl moiety on the electronic interaction was studied using electrochemistry (cyclic and square-wave voltammetry) and spectro-electrochemistry (in situ UV/Vis-NIR spectroscopy). The ferrocenyl moieties gave rise to two sequential, reversible redox processes in each of the diferrocenyl-1-phenyl-1H-pyrroles. The observed ΔE(1/2) values (ΔE(1/2) = difference between first and second oxidation) range between 420 and 480 mV. A linear relationship between the Hammett constants σ of the substituents and the separation of the redox potentials exists. The NIR measurements confirm electronic communication between the iron centers as intervalence charge transfer (IVCT) absorptions were observed in the corresponding mixed-valent monocationic species. All compounds were classified as class II systems according to Robin and Day (M. B. Robin and P. Day, Adv. Inorg. Chem., 1967, 10, 247-423). The oscillator strength of the charge transfer transition highly depends on the electron donating or electron withdrawing character of the phenyl substituents. This enables direct tuning of the intermetallic communication by simple modification of the molecule's functional group. Hence, this series of molecules may be regarded as model compounds for single molecule transistors.

40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

Code of Federal Regulations, 2014 CFR

2014-07-01

...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section for...

40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

Code of Federal Regulations, 2011 CFR

2011-07-01

...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section for...

40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

Code of Federal Regulations, 2012 CFR

2012-07-01

...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section for...

40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

Code of Federal Regulations, 2010 CFR

2010-07-01

...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section for...

40 CFR 721.984 - Amino-hydroxy sulfonaphthylazo-disubstituted phenyl azo benzene carboxylate salt (generic).

Code of Federal Regulations, 2013 CFR

2013-07-01

...-disubstituted phenyl azo benzene carboxylate salt (generic). 721.984 Section 721.984 Protection of Environment...-disubstituted phenyl azo benzene carboxylate salt (generic). (a) Chemical substance and significant new uses...-disubstituted phenyl azo benzene carboxylate salt (PMN P-00-0351) is subject to reporting under this section for...

Alkylarylnitrosoureas--stability in aqueous solution, partition coefficient, alkylating activity and its relationship to SCE induction in Chinese hamster V 79-E cells.

PubMed

Mendel, J; Thust, R; Schwarz, H

1982-01-01

The alkylating activity, chemical stability in aqueous solution (pH 7.0; 37 degrees C), and partition coefficient (octanol/water) of the following compounds were determined: 1-methyl-3-phenyl-1-nitrosourea (MPNU), 1-ethyl-3-phenyl-1-nitrosourea (EPNU), 1-isopropyl-3-phenyl-1-nitrosourea (i-PrPNU), 1-methyl-3-(p-fluorophenyl)-1-nitrosourea (F-MPNU), 1-methyl-3-(p-chlorophenyl)-1-nitrosourea (Cl-MPNU), 1-methyl-3-(p-bromophenyl)-1-nitrosourea (Br-MPNU), 1,3-dimethyl-3-phenyl-1-nitrosourea (DMPNU), and 1-methyl-3-naphthyl-1-nitrosocarbamate (NCA). 1-Methyl-1-nitrosourea (MNU) and 1-ethyl-1-nitrosourea (ENU) were used for the comparison. THe rate of decomposition in aqueous solution is discussed concerning the influences of the substituents at the 1- and 3-N-atom. The mono- and disubstituted N-nitrosoureas showed a coarse correlation between alkylating activity and SCE induction in Chinese hamster V 79-E cells. On the other hand, this correlation is missing in the case of NCA, which is a potent SCE inducer despite relatively low alkylating activity. DMPNU is the strongest SCE inducer, but this compound shows a high stability in aqueous solution and, consequently, we were not able to detect an alkylating activity.

Bis(tetra­phenyl­phospho­nium) tetra­chlorido­cobaltate(II)

PubMed Central

Ouahida, Zeghouan; Hadjadj, Nasreddine; Guenifa, Fatiha; Bendjeddou, Lamia; Merazig, Hocine

2014-01-01

The title compound, (C24H20P)2[CoCl4], was prepared under hydro­thermal conditions. In the crystal, the tetra­phenyl­phospho­nium cations are linked by pairs of weak C—H⋯π inter­actions into supra­molecular dimers; the CoII cations lie on twofold rotation axes and the tetra­hedral [CoCl4]2− anions are linked with the tetra­phenyl­phospho­nium cations via weak C—H⋯Cl hydrogen bonds. PMID:24940211

Biosynthesis of (R)-phenyl-1,2-ethanediol from racemic styrene oxide by using bacterial and marine fish epoxide hydrolases.

PubMed

Kim, Hee Sook; Lee, Ok Kyung; Hwang, Seungha; Kim, Beum Jun; Lee, Eun Yeol

2008-01-01

Enantio-convergent hydrolysis of racemic styrene oxides was achieved to prepare enantiopure (R)-phenyl-1,2-ethanediol by using two recombinant epoxide hydrolases (EHs) of a bacterium, Caulobacter crescentus, and a marine fish, Mugil cephalus. The recombinant C. crescentus EH primarily attacked the benzylic carbon of (S)-styrene oxide, while the M. cephalus EH preferentially attacked the terminal carbon of (R)-styrene oxide, thus leading to the formation of (R)-phenyl-1,2-ethanediol as the main product. (R)-Phenyl-1,2-ethanediol was obtained with 90% enantiomeric excess and yield as high as 94% from 50 mM racemic styrene oxides in a one-pot process.

In vitro and in vivo characterization of JNJ-31020028 (N-(4-{4-[2-(diethylamino)-2-oxo-1-phenylethyl]piperazin-1-yl}-3-fluorophenyl)-2-pyridin-3-ylbenzamide), a selective brain penetrant small molecule antagonist of the neuropeptide Y Y(2) receptor.

PubMed

Shoblock, James R; Welty, Natalie; Nepomuceno, Diane; Lord, Brian; Aluisio, Leah; Fraser, Ian; Motley, S Timothy; Sutton, Steve W; Morton, Kirsten; Galici, Ruggero; Atack, John R; Dvorak, Lisa; Swanson, Devin M; Carruthers, Nicholas I; Dvorak, Curt; Lovenberg, Timothy W; Bonaventure, Pascal

2010-02-01

The lack of potent, selective, brain penetrant Y(2) receptor antagonists has hampered in vivo functional studies of this receptor. Here, we report the in vitro and in vivo characterization of JNJ-31020028 (N-(4-{4-[2-(diethylamino)-2-oxo-1-phenylethyl]piperazin-1-yl}-3-fluorophenyl)-2-pyridin-3-ylbenzamide), a novel Y(2) receptor antagonist. The affinity of JNJ-31020028 was determined by inhibition of the PYY binding to human Y(2) receptors in KAN-Ts cells and rat Y(2) receptors in rat hippocampus. The functional activity was determined by inhibition of PYY-stimulated calcium responses in KAN-Ts cells expressing a chimeric G protein Gqi5 and in the rat vas deferens (a prototypical Y(2) bioassay). Ex vivo receptor occupancy was revealed by receptor autoradiography. JNJ-31020028 was tested in vivo with microdialysis, in anxiety models, and on corticosterone release. JNJ-31020028 bound with high affinity (pIC(50) = 8.07 +/- 0.05, human, and pIC(50) = 8.22 +/- 0.06, rat) and was >100-fold selective versus human Y(1), Y(4), and Y(5) receptors. JNJ-31020028 was demonstrated to be an antagonist (pK(B) = 8.04 +/- 0.13) in functional assays. JNJ-31020028 occupied Y(2) receptor binding sites (approximately 90% at 10 mg/kg) after subcutaneous administration in rats. JNJ-31020028 increased norepinephrine release in the hypothalamus, consistent with the colocalization of norepinephrine and neuropeptide Y. In a variety of anxiety models, JNJ-31020028 was found to be ineffective, although it did block stress-induced elevations in plasma corticosterone, without altering basal levels, and normalized food intake in stressed animals without affecting basal food intake. These results suggest that Y(2) receptors may not be critical for acute behaviors in rodents but may serve modulatory roles that can only be elucidated under specific situational conditions.

Interactions of 2-phenyl-benzotriazole xenobiotic compounds with human Cytochrome P450-CYP1A1 by means of docking, molecular dynamics simulations and MM-GBSA calculations.

PubMed

Mena-Ulecia, Karel; MacLeod-Carey, Desmond

2018-06-01

2-phenyl-benzotriazole xenobiotic compounds (PBTA-4, PBTA-6, PBTA-7 and PBTA-8) that were previously isolated and identified in waters of the Yodo river, in Japan (Nukaya et al., 2001; Ohe et al., 2004; Watanabe et al., 2001) were characterized as powerful pro-mutagens. In order to predict the activation mechanism of these pro-mutagens, we designed a computational biochemistry protocol, which includes, docking experiments, molecular dynamics simulations and free energy decomposition calculations to obtain information about the interaction of 2-phenyl-benzotriazole molecules into the active center of cytochrome P450-CYP1A1 (CYP1A1). Molecular docking calculations using AutoDock Vina software shows that PBTAs are proportionally oriented in the pocket of CYP1A1, establishing π-π stacking attractive interactions between the triazole group and the Phe224, as well as, the hydrogen bonds of the terminal NH 2 over the benzotriazole units with the Asn255 and Ser116 amino acids. Molecular dynamics simulations using NAMD package showed that these interactions are stable along 100.0 ns of trajectories. Into this context, free binding energy calculations employing the MM-GBSA approach, shows that some differences exists among the interaction of PBTAs with CYP1A1, regarding the solvation, electrostatic and van der Waals interaction energy components. These results suggest that PBTA molecules might be activated by CYP1A1. Thus, enhancing their mutagenicity when compared with the pro-mutagen parent species. Copyright © 2018 Elsevier Ltd. All rights reserved.

Toward the definition of stereochemical requirements for MT2-selective antagonists and partial agonists by studying 4-phenyl-2-propionamidotetralin derivatives.

PubMed

Bedini, Annalida; Lucarini, Simone; Spadoni, Gilberto; Tarzia, Giorgio; Scaglione, Francesco; Dugnani, Silvana; Pannacci, Marilou; Lucini, Valeria; Carmi, Caterina; Pala, Daniele; Rivara, Silvia; Mor, Marco

2011-12-22

New derivatives of 4-phenyl-2-propionamidotetralin (4-P-PDOT) were prepared and tested on cloned MT1 and MT2 receptors, with the purpose of merging previously reported pharmacophores for nonselective agonists and for MT2-selective antagonists. A 8-methoxy group increases binding affinity of both (±)-cis- and (±)-trans-4-P-PDOT, and it can be bioisosterically replaced by a bromine. Conformational analysis of 8-methoxy-4-P-PDOT by molecular dynamics, supported by NMR data, revealed an energetically favored conformation for the (2S,4S)-cis isomer and a less favorable conformation for the (2R,4S)-trans one, fulfilling the requirements of a pharmacophore model for nonselective melatonin receptor agonists. A new superposition model, including features characteristic of MT2-selective antagonists, suggests that MT1/MT2 agonists and MT2 antagonists can share the same arrangement for their pharmacophoric elements. The model correctly predicted the eutomers of (±)-cis- and (±)-trans-4-P-PDOT. The model was validated by preparing three dihydronaphthalene derivatives, either able or not able to reproduce the putative active conformation of 4-P-PDOT.

A comparison of 2-phenyl-2-(1-piperidinyl)propane (ppp), 1,1',1''-phosphinothioylidynetrisaziridine (thioTEPA), clopidogrel, and ticlopidine as selective inactivators of human cytochrome P450 2B6.

PubMed

Walsky, Robert L; Obach, R Scott

2007-11-01

The use of selective chemical inhibitors of human cytochrome P450 (P450) enzymes represents a powerful method by which the relative contributions of various human P450 enzymes to the metabolism of drugs can be determined. However, the identification of CYP2B6 in the metabolism of drugs has been more challenging because of the lack of a well established inhibitor of this enzyme. In this report, we describe the selectivity of 2-phenyl-2-(1-piperidinyl)propane (PPP) as an inactivator of CYP2B6 and compare this selectivity versus other CYP2B6 inactivators: 1,1',1''-phosphinothioylidynetrisaziridine (thioTEPA), clopidogrel, and ticlopidine. Values of K(I) and k(inact) for PPP were 5.6 microM and 0.13/min for bupropion hydroxylase catalyzed by pooled human liver microsomes, and values for thioTEPA were similar (4.8 microM and 0.20/min, respectively). Intrinsic inactivation capability was considerably greater for clopidogrel because of a greater k(inact) value (1.9/min). Ticlopidine was potent with K(I) and k(inact) values of 0.32 microM and 0.43/min, respectively. The selectivity of these four agents for CYP2B6 was determined by testing their effects on other human P450 enzyme activities using conditions that yield approximately 90% inactivation of CYP2B6 activity. The results showed that preincubation of human liver microsomes with PPP at 30 microM for 30 min provided more selective inhibition for CYP2B6 than thioTEPA, clopidogrel, and ticlopidine. Furthermore, the use of clopidogrel is complicated by the observation that this agent is not stable in the presence of human liver microsomes, even without addition of NADPH. Therefore, PPP can serve as a selective chemical inactivator of CYP2B6 and be used to define the role of CYP2B6 in the metabolism of drugs.

Functionalization of gold and graphene electrodes by p-maleimido-phenyl towards thiol-sensing systems investigated by EQCM and IR ellipsometric spectroscopy

NASA Astrophysics Data System (ADS)

Neubert, Tilmann J.; Rösicke, Felix; Sun, Guoguang; Janietz, Silvia; Gluba, Marc A.; Hinrichs, Karsten; Nickel, Norbert H.; Rappich, Jörg

2017-11-01

Electrografting of gold and graphene surfaces by functional p-(N-maleimido)phenyl groups was performed by reduction of p-(N-maleimido)phenyldiazonium tetrafluoroborate. The reduction was carried out using cyclic voltammetry coupled with micro-gravimetric measurements by means of electrochemical quartz crystal microbalance (EQCM). The overall deposited mass on gold was higher than on graphene. However, the Faradaic efficiency was lower on Au (14%) compared to graphene (22%) after the first potential scan. Subsequently, the maleimide functional groups have been tested for immobilization of terminal thiols using (4-nitrobenzyl)mercaptan for the functionalized graphene surface and a cysteine-modified peptide for the functionalized gold surface. The functionalization by p-(N-maleimido)phenyl groups and the following thiol coupling of the particular surface was proven by infrared spectroscopic ellipsometry (IRSE). In addition, the interaction of the tetrabutylammonium and tetrafluoroborate ions present in the electrolyte with the Au and graphene electrodes was investigated by EQCM and revealed less electrostatic interaction of graphene with these ions in solution compared to the metal (Au) surface.

Sleep-inducing N-alkyl-5-[m-(trifluoromethyl)phenyl]-5-hydroxy-2-pyrrolidinones and N-alkyl-3-(trifluoromethyl)cinnamamides.

PubMed

Houlihan, W J; Gogerty, J H; Ryan, E A; Schmitt, G

1985-01-01

A series of N-alkyl-3-[m-(trifluoromethyl)phenyl]-5-hydroxy-2-pyrrolidinones and N-alkyl-3-(trifluoromethyl)-cinnamamides were prepared and screened in a series of tests designed to detect potential sleep inducers. The more active members of the series were evaluated for their ability to induce sleep in Cebus monkeys. The most active compound, N-methyl-5-[m-(trifluoromethyl)phenyl]-5-hydroxy-2-pyrrolidinone, was equal to methaqualone.

Triphenyltin derivatives of sulfanylcarboxylic esters.

PubMed

Casas, José S; Couce, María D; Sánchez, Agustín; Seoane, Rafael; Sordo, José; Perez-Estévez, Antonio; Vázquez-López, Ezequiel

2018-03-01

The reaction of 3-(aryl)-2-sulfanylpropenoic acids [H 2 xspa; x: p=3-phenyl-, f=3-(2-furyl)-, t=3-(2-thienyl)-] with methanol or ethanol gave the corresponding methyl (Hxspme) or ethyl (Hxspee) esters. The reaction of these esters (HL) with triphenyltin(IV) hydroxide gave compounds of the type [SnPh 3 L], which were isolated and characterized as solids by elemental analysis, IR spectroscopy and mass spectrometry and in solution by multinuclear ( 1 H, 13 C and 119 Sn) NMR spectroscopy. The structures of [SnPh 3 (pspme)], [SnPh 3 (fspme)] and [SnPh 3 (fspee)] were determined by X-ray diffractometry and the antimicrobial activity against E. coli, S. aureus, B. subtilis, P. aeruginosa, Resistant P. aeruginosa (a strain resistant to 'carbapenem'), and C. albicans was tested and the in vitro cytotoxic activity against the HeLa-229, A2780 and A2780cis cell lines was determined for all compounds. Copyright © 2017 Elsevier Inc. All rights reserved.

Preclinical pharmacokinetic characterization of 2-(4-(4-(5-(2-phenyl-5-(trifluoromethyl)oxazole-4-carboxamido)-1H-benzo[d]imidazol-2-yl)phenyl)cyclohexyl) acetic acid, a novel DGAT-1 inhibitor.

PubMed

Kwak, Eun-Young; Im, So Hee; Seo, Hyewon; Cho, Woon-Ki; Lee, Ye-Lim; Woo, Jaechun; Ahn, Sunjoo; Ahn, Sung-Hoon; Kwak, Hyun Jung; Ahn, Jin Hee; Bae, Myung Ae; Song, Jin Sook

2014-05-01

1. A novel diacylglyceride acyltransferase-1 (DGAT-1) inhibitor, 2-(4-(4-(5-(2-phenyl-5-(trifluoromethyl) oxazole-4-carboxamido)-1H-benzo[d]imidazol-2-yl)phenyl)cyclohexyl) acetic acid (KR-69232), was synthesized for a potential therapeutic use against several metabolic disorders, such as obesity, insulin resistance, and type II diabetes, characterized by excessive triglycerides (TGs) in the blood. 2. The half-lives against phase I metabolism were measured as 75.3 ± 20.9 min and over 120 min in rat and human liver microsomes, respectively. In Caco-2 cell monolayers, extremely low permeability (<0.13 × 10⁻⁶cm/s) was seen in the absorptive direction, predicting limited intestinal absorption of KR-69232. This compound was highly bound to rat and human plasma proteins (>99.8%). 3. With the intravenous administration of KR-69232 in rats (1, 2, and 5 mg/kg), non-linear kinetics were observed at the highest dose, with significantly higher systemic clearance, higher volume of distribution, and lower dose-normalized AUC. Following oral administration, it exhibited low bioavailability (<10%) and was absorbed slowly (T(max), 3.8-5.2 h) over the dose range. We also confirmed that considerable KR-69232 remained in the intestine at T(max), demonstrating its limited absorption into the systemic circulation.

Preparation and Characterization of Flexible Substrate Material from Phenyl-Thiophene-2-Carbaldehyde Compound.

PubMed

Rahman, Ashiqur; Islam, Mohammad Tariqul; Samsuzzaman, Md; Singh, Mandeep Jit; Akhtaruzzaman, Md

2016-05-11

In this paper, a novel phenyl-thiophene-2-carbaldehyde compound-based flexible substrate material has been presented. Optical and microwave characterization of the proposed material are done to confirm the applicability of the proposed material as a substrate. The results obtained in this work show that the phenyl-thiophene-2-carbaldehyde consists of a dielectric constant of 3.03, loss tangent of 0.003, and an optical bandgap of 3.24 eV. The proposed material is analyzed using commercially available EM simulation software and validated by the experimental analysis of the flexible substrate. The fabricated substrate also shows significant mechanical flexibility and light weight. The radiating copper patch deposited on the proposed material substrate incorporated with partial ground plane and microstrip feeding technique shows an effective impedance bandwidth of 3.8 GHz. It also confirms an averaged radiation efficiency of 81% throughout the frequency band of 5.4-9.2 GHz.

Preparation and Characterization of Flexible Substrate Material from Phenyl-Thiophene-2-Carbaldehyde Compound

PubMed Central

Rahman, Ashiqur; Islam, Mohammad Tariqul; Samsuzzaman, Md; Singh, Mandeep Jit; Akhtaruzzaman, Md.

2016-01-01

In this paper, a novel phenyl-thiophene-2-carbaldehyde compound-based flexible substrate material has been presented. Optical and microwave characterization of the proposed material are done to confirm the applicability of the proposed material as a substrate. The results obtained in this work show that the phenyl-thiophene-2-carbaldehyde consists of a dielectric constant of 3.03, loss tangent of 0.003, and an optical bandgap of 3.24 eV. The proposed material is analyzed using commercially available EM simulation software and validated by the experimental analysis of the flexible substrate. The fabricated substrate also shows significant mechanical flexibility and light weight. The radiating copper patch deposited on the proposed material substrate incorporated with partial ground plane and microstrip feeding technique shows an effective impedance bandwidth of 3.8 GHz. It also confirms an averaged radiation efficiency of 81% throughout the frequency band of 5.4–9.2 GHz. PMID:28773479

Effect of substituents on redox, spectroscopic and structural properties of conjugated diaryltetrazines--a combined experimental and theoretical study.

PubMed

Kurach, Ewa; Djurado, David; Rimarčik, Jan; Kornet, Aleksandra; Wlostowski, Marek; Lukeš, Vladimir; Pécaut, Jacques; Zagorska, Malgorzata; Pron, Adam

2011-02-21

Two series of new soluble conjugated compounds containing tetrazine central ring have been synthesized. The three-ring compounds have been synthesized by the reaction of aryl cyanide (where aryl = thienyl, alkylthienyl, phenyl or pyridyl) with hydrazine followed by oxidation of the intermediate product with diethyl azodicarboxylate. The five-ring compounds have been prepared using two pathways: (i) reaction of 5-cyano-2,2'-bithiophene (or its alkyl derivative) with hydrazine; (ii) via Suzuki or Stille coupling of 3,6-bis(5-bromo-2-thienyl)-1,2,4,5-tetrazine with a stannyl or boronate derivative of alkylthiophene. UV-vis spectroscopic properties of the synthesized compounds are strongly dependent on the nature of the aryl group, the position of the solubilizing substituent and the length of the molecule, showing the highest bathochromic shift (λ(max) > 440 nm) for five-ring compounds with alkyl groups attached to C(α) carbon in the terminal thienyl ring. An excellent linear correlation has been found for spectroscopically determined and theoretically calculated (TD-B3LYP/6-31G*) excitation energies. With the exception of dipyridyl derivative, the calculated lowest unoccupied molecular orbital (LUMO) level of the investigated molecules changes within a narrow range (from -2.63 to -2.41 eV), in line with the electrochemical data, which show a reversible reduction process with the redox potential varying from -1.23 V to -1.33 V (vs. Fc/Fc(+)). The electrochemically determined positions of the LUMO levels are consistently lower by 0.9 to 1.2 eV with respect to the calculated ones. All molecules readily crystallize. Single crystal studies of 3,6-bis(2,2'-bithien-5-yl)-1,2,4,5-tetrazine show that it crystallizes in a P2(1)/c space group whose structural arrangement is not very favorable to the charge carriers flow within the crystal. Powder diffraction studies of other derivatives have shown that their structural organization is sensitive to the position of the

40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound with...

40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound with...

40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

Code of Federal Regulations, 2013 CFR

2013-07-01

... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound with...

40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound with...

40 CFR 721.5356 - Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl]-omega...

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Ethanol, 2,2â²2â³-nitrilotris... Substances § 721.5356 Ethanol, 2,2′2″-nitrilotris-, compound with alpha-2,4,6-tris (1-phenylethyl)phenyl... subject to reporting. (1) The chemical substance identified as ethanol, 2,2′2″-nitrilotris-, compound with...

Design, synthesis, and anti-melanogenic effects of (E)-2-benzoyl-3-(substituted phenyl)acrylonitriles

PubMed Central

Yun, Hwi Young; Kim, Do Hyun; Son, Sujin; Ullah, Sultan; Kim, Seong Jin; Kim, Yeon-Jeong; Yoo, Jin-Wook; Jung, Yunjin; Chun, Pusoon; Moon, Hyung Ryong

2015-01-01

Background Tyrosinase is the most prominent target for inhibitors of hyperpigmentation because it plays a critical role in melaninogenesis. Although many tyrosinase inhibitors have been identified, from both natural and synthetic sources, there remains a considerable demand for novel tyrosinase inhibitors that are safer and more effective. Methods (E)-2-Benzoyl-3-(substituted phenyl)acrylonitriles (BPA analogs) with a linear β-phenyl-α,β-unsaturated carbonyl scaffold were designed and synthesized as potential tyrosinase inhibitors. We evaluated their effects on cellular tyrosinase activity and melanin biosynthesis in murine B16F10 melanoma cells and their ability to inhibit mushroom tyrosinase activity. Results BPA analogs exhibited inhibitory activity against mushroom tyrosinase. In particular, BPA13 significantly suppressed melanin biosynthesis and inhibited cellular tyrosinase activity in B16F10 cells in a dose-dependent manner. A docking study revealed that BPA13 had higher binding affinity for tyrosinase than kojic acid. Conclusion BPA13, which possesses a linear β-phenyl-α,β-unsaturated carbonyl scaffold, is a potential candidate skin-whitening agent and treatment for diseases associated with hyperpigmentation. PMID:26347064

Different molecular conformations co-exist in each of three 2-aryl-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamides: hydrogen bonding in zero, one and two dimensions.

PubMed

Narayana, Badiadka; Yathirajan, Hemmige S; Rathore, Ravindranath S; Glidewell, Christopher

2016-09-01

4-Antipyrine [4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one] and its derivatives exhibit a range of biological activities, including analgesic, antibacterial and anti-inflammatory, and new examples are always of potential interest and value. 2-(4-Chlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide, C19H18ClN3O2, (I), crystallizes with Z' = 2 in the space group P\\overline{1}, whereas its positional isomer 2-(2-chlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide, (II), crystallizes with Z' = 1 in the space group C2/c; the molecules of (II) are disordered over two sets of atomic sites having occupancies of 0.6020 (18) and 0.3980 (18). The two independent molecules of (I) adopt different molecular conformations, as do the two disorder components in (II), where the 2-chlorophenyl substituents adopt different orientations. The molecules of (I) are linked by a combination of N-H...O and C-H...O hydrogen bonds to form centrosymmetric four-molecule aggregates, while those of (II) are linked by the same types of hydrogen bonds forming sheets. The related compound N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-(3-methoxyphenyl)acetamide, C20H21N3O3, (III), is isomorphous with (I) but not strictly isostructural; again the two independent molecules adopt different molecular conformations, and the molecules are linked by N-H...O and C-H...O hydrogen bonds to form ribbons. Comparisons are made with some related structures, indicating that a hydrogen-bonded R2(2)(10) ring is the common structural motif.

40 CFR 721.2465 - Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate.

Code of Federal Regulations, 2010 CFR

2010-07-01

... Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.2465 Xanthylium, 9-(2-(ethoxycarbonyl)phenyl)-3,6-bis(ethylamino)-2,7-dimethyl-, ethyl sulfate. (a) Chemical substance and significant...

Structure-based design synthesis of functionalized 3-(5-(s-phenyl)-4H-pyrazol-3-yl)-2H-chromen-2-one motifs and indigenous plant extracts and their antimalarial potential

NASA Astrophysics Data System (ADS)

Olayinka, Ajani; Grace, Olasehinde; Titilope, Dokunmu; Ruth, Diji-Geske; Olabode, Onileere; John, Openibo; Oreoluwa, Oluseye; Tochukwu, Chileke; Ezekiel, Adebiyi

2018-04-01

Resistance of the malaria parasite to conventional therapeutic agents calls for increased efforts in antimalarial drug discovery. Current efforts should be targeted at developing safe and affordable new agents to counter the spread of malaria parasites that are resistant to existing therapy. In this study, toxicological and in vivo antiplasmodial properties of 3-(5-(s-phenyl)-4H-pyrazol-3-yl)-42H-chromen-2, Mangifera indica and Tithonia diversifolia in swiss albino mice models, Musmusculus were investigated. 2H-Chromen-2-one also known as coumarin is highly privileged oxygen-containing heterocyclic entity which are present in plant kingdom as secondary metabolites. The maceration technique of crude drug extraction was employed using cold water extraction. Toxicological analysis was carried out using Lorke's method for acute toxicity testing while the chemosuppressive activity was carried out using Peter's four day test on early infection. We also report the synthesis of functionalized 3-(5-(s-phenyl)-4H-pyrazol-3-yl)-2H-chromen-2-one motifs via microwave assisted synthetic approach and isolation of indigenous plant extract in order to investigate their antimalarial efficacy. The condensation reaction of 3-acetylcoumarin with various benzaldehyde derivatives resulted in the formation of 3-[3-acryloyl]-2H-chromen-2-one which was subsequently reaction the hydrazine hydrate via microwave assisted hydrazinolysis to afford the targeted 3-(5-(s-phenyl)-4H-pyrazol-3-yl)-2H-chromen-2-one motifs. The chemical structures were confirmed by analytical data and spectroscopic means such as FT-IR, UV, 1H NMR, 13C NMR and DEPT-135. The microwave assisted reaction was remarkably successful and gave targeted 3-(5-(s-phenyl)-4H-pyrazol-3-yl)-2H-chromen-2-one motifs in higher yields at lesser reaction time compared to conventional heating method. The LD50 of the aqueous extracts of the leaves and stem bark Mangifera indica was established to be ± 707.11 mg/kg b.w., p.o. (body weight

1-Formyl-3-phenyl-5-(4-isopropylphenyl)-2-pyrazoline: Synthesis, characterization, antimicrobial activity and DFT studies

NASA Astrophysics Data System (ADS)

Sid, Assia; Messai, Amel; Parlak, Cemal; Kazancı, Nadide; Luneau, Dominique; Keşan, Gürkan; Rhyman, Lydia; Alswaidan, Ibrahim A.; Ramasami, Ponnadurai

2016-10-01

The structure of 1-formyl-3-phenyl-5-(4-isopropylphenyl)-2-pyrazoline synthesized as single crystal was investigated by FTIR, NMR, XRD. Experimental data were complemented by quantum mechanical calculations. XRD data show that the compound crystallizes in the triclinic system (P-1) via trans isomer (a = 6.4267(4) Å, b = 10.9259(12) Å, c = 12.4628(9) Å and α = 102.894(8)°, β = 102.535(6)°, γ = 101.633(7)°). Anti-microbial screening results indicate that the compound shows promising activity. The theoretically predicted and experimentally obtained parameters reveal further insight into pyrazoline systems.

Dangguijakyak-san protects dopamine neurons against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurotoxicity under postmenopausal conditions.

PubMed

Lee, Jin-Moo; Hwang, Deok-Sang; Kim, Hyo Geun; Lee, Chang-Hoon; Oh, Myung Sook

2012-02-15

Dangguijakyak-san protects dopamine neurons against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurotoxicity under postmenopausal conditions. Dangguijakyak-san (DJS), a famous traditional herbal formula, has long been used to treat gynecological disorders, including postmenopausal symptoms. This study evaluated the effects and mechanism of DJS on 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced neurotoxicity in a postmenopausal mouse model induced by ovariectomy. Three weeks after ovariectomy, C57bl/6 female mice were divided randomly into (1) control, (2) MPTP (30 mg/kg/day, i.p., 5 days), (3) MPTP+estrogen (50 μg/kg/day, i.p., 5 days), and (4) MPTP+DJS (50 mg/kg/day, p.o., 5 days) groups. We investigated the behavioral recovery and dopamine neuron protection of DJS using the pole test and tyrosine hydroxylase (TH) immunohistochemistry. We also explored the mechanism by assessing the protein expression of Bax, Bcl-2, cytochrome c, and cleaved caspase-3. DJS treatment restored the movement behavior impaired by MPTP, showing a similar or better effect than estrogen. DJS protected TH-immunoreactive cells and fibers in the nigrostriatal region from MPTP toxicity. In addition, DJS inhibited the Bcl-2 decrease and Bax increase in mitochondria, cytochrome c release to the cytosol, and caspase-3 activation induced by MPTP. DJS showed behavior recovery and dopamine neuron protection against MPTP-induced toxicity via anti-apoptotic activities in ovariectomized female mice. These results suggest that DJS treatment is effective for postmenopausal neurodegenerative diseases. Copyright © 2011 Elsevier Ireland Ltd. All rights reserved.

3-Phenylpropanoic acid-based phosphotyrosine (pTyr) mimetics: hit evolution to a novel orally active protein tyrosine phosphatase 1B (PTP1B) inhibitor.

PubMed

Tang, Yan-Bo; Liu, Jun-Zheng; Zhang, Shu-En; Du, Xin; Nie, Feilin; Tian, Jin-Ying; Ye, Fei; Huang, Kai; Hu, Jin-Ping; Li, Yan; Xiao, Zhiyan

2014-05-01

Protein tyrosine phosphatase 1B (PTP1B) is a promising therapeutic target for type 2 diabetes. Herein, we report the evolution of a previously identified 3-phenylpropanoic acid-based PTP1B inhibitor to an orally active lead compound. A series of 3-phenylpropanoic acid-based PTP1B inhibitors were synthesized, and three of them, 3-(4-(9H-carbazol-9-yl)phenyl)-5-(3,5-di-tert-butyl-4-methoxyphenyl)-5-oxopentanoic acid (9), 3-(4-(9H-carbazol-9-yl)phenyl)-5-(4'-bromo-[1,1'-biphenyl]-4-yl)-5-oxopentanoic acid (10) and 3-(4-(9H-carbazol-9-yl)-2-fluorophenyl)-5-(4-cyclohexylphenyl)-5-oxopentanoic acid (16), showed IC50 values at sub-micromolar level. Further in vivo evaluation indicated the sodium salt of 9 not only exhibited significant insulin-sensitizing and hypoglycemia effects, but also decreased the serum levels of triglyceride and total cholesterol in high-fat-diet-induced insulin resistance model mice. Preliminary in vivo pharmacokinetic studies on the sodium salt of 9 revealed its pharmacokinetic profile after oral administration in rats. These results provide proof-of-concept for the dual effects of PTP1B inhibitors on both glucose and lipid metabolisms. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Two polymorphs of 2,5-dichloro-3,6-bis(dibenzylamino)-p-hydroquinone with flexible dibenzylamino groups.

PubMed

Shin, In Sub; Shimada, Yuta; Horiguchi-Babamoto, Emi; Matsumoto, Shinya

2018-04-01

We obtained two conformational polymorphs of 2,5-dichloro-3,6-bis(dibenzylamino)-p-hydroquinone, C 34 H 30 Cl 2 N 2 O 2 . Both polymorphs have an inversion centre at the centre of the hydroquinone ring (Z' = 1/2), and there are no significant differences between their bond lengths and angles. The most significant structural difference in the molecular conformations was found in the rotation of the phenyl rings of the two crystallographically independent benzyl groups. The crystal structures of the polymorphs were distinguishable with respect to the arrangement of the hydroquinone rings and the packing motif of the phenyl rings that form part of the benzyl groups. The phenyl groups of one polymorph are arranged in a face-to-edge motif between adjacent molecules, with intermolecular C-H...π interactions, whereas the phenyl rings in the other polymorph form a lamellar stacking pattern with no significant intermolecular interactions. We suggest that this partial conformational difference in the molecular structures leads to the significant structural differences observed in their molecular arrangements.

21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

Code of Federal Regulations, 2012 CFR

2012-04-01

.... The color additive2-[[2,5-diethoxy-4-[(4-methylphenyl)thio]phenyl]azo]-1,3,5-benzenetriol is formed in situ in soft (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2-[[2,5... following restrictions: (1) The quantity of the color additive does not exceed 1.1×10−7 grams in a soft...

21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

Code of Federal Regulations, 2011 CFR

2011-04-01

.... The color additive2-[[2,5-diethoxy-4-[(4-methylphenyl)thio]phenyl]azo]-1,3,5-benzenetriol is formed in situ in soft (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2-[[2,5... following restrictions: (1) The quantity of the color additive does not exceed 1.1×10−7 grams in a soft...

21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

Code of Federal Regulations, 2013 CFR

2013-04-01

.... The color additive2-[[2,5-diethoxy-4-[(4-methylphenyl)thio]phenyl]azo]-1,3,5-benzenetriol is formed in situ in soft (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2-[[2,5... following restrictions: (1) The quantity of the color additive does not exceed 1.1×10−7 grams in a soft...

21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

Code of Federal Regulations, 2014 CFR

2014-04-01

.... The color additive2-[[2,5-diethoxy-4-[(4-methylphenyl)thio]phenyl]azo]-1,3,5-benzenetriol is formed in situ in soft (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2-[[2,5... following restrictions: (1) The quantity of the color additive does not exceed 1.1×10−7 grams in a soft...

21 CFR 73.3115 - 2-[[2,5-Diethoxy-4-[(4-methylphenyl)thiol]phenyl]azo]-1,3,5-benzenetriol.

Code of Federal Regulations, 2010 CFR

2010-04-01

.... The color additive2-[[2,5-diethoxy-4-[(4-methylphenyl)thio]phenyl]azo]-1,3,5-benzenetriol is formed in situ in soft (hydrophilic) contact lenses. (b) Uses and restrictions. The color additive 2-[[2,5... following restrictions: (1) The quantity of the color additive does not exceed 1.1×10−7 grams in a soft...

Crystal structure of a mixed-ligand dinuclear Ba-Zn complex with 2-meth-oxy-ethanol having tri-phenyl-acetate and chloride bridges.

PubMed

Utko, Józef; Sobocińska, Maria; Dobrzyńska, Danuta; Lis, Tadeusz

2015-07-01

The dinuclear barium-zinc complex, μ-chlorido-1:2κ(2) Cl:Cl-chlorido-2κCl-bis-(2-meth-oxy-ethanol-1κO)bis-(2-meth-oxy-ethanol-1κ(2) O,O')bis-(μ-tri-phenyl-acetato-1:2κ(2) O:O')bariumzinc, [BaZn(C20H15O2)2Cl2(C3H8O2)4], has been synthesized by the reaction of barium tri-phenyl-acetate, anhydrous zinc chloride and 2-meth-oxy-ethanol in the presence of toluene. The barium and zinc metal cations in the dinuclear complex are linked via one chloride anion and carboxyl-ate O atoms of the tri-phenyl-acetate ligands, giving a Ba⋯Zn separation of 3.9335 (11) Å. The irregular nine-coordinate BaO8Cl coordination centres comprise eight O-atom donors, six of them from 2-meth-oxy-ethanol ligands (four from two bidentate O,O'-chelate inter-actions and two from monodentate inter-actions), two from bridging tri-phenyl-acetate ligands and one from a bridging Cl donor. The distorted tetra-hedral coordination sphere of zinc comprises two O-atom donors from the tri-phenyl-acetate ligands and two Cl donors (one bridging and one terminal). In the crystal, O-H⋯Cl, O-H⋯O and C-H⋯Cl inter-molecular inter-actions form a layered structure, lying parallel to (001).

Conformational dynamics in fluorophenylcarbamoyl-alpha-chymotrypsins.

PubMed

Kairi, M; Gerig, J T

1990-06-19

A series of fluorine-substituted diphenylcarbamoyl chlorides have been synthesized and used to prepare corresponding diphenylcarbamoylated derivatives of alpha-chymotrypsin. The enzyme is rapidly inactivated by these compounds, as has been previously observed for the unsubstituted chloride, and the derivatives are stable enough to permit extensive studies by fluorine NMR spectroscopy. In combination with previously reported results, these NMR experiments suggest that the aromatic rings of a diphenylcarbamoyl group attached to chymotrypsin may be found in two magnetically and dynamically distinguishable sites, with exchange between these sites taking place by a process that involves rotation about the carbamoyl N-CO bond and localized unfolding of the enzyme. The extent to which a given fluoroaromatic ring is found in one of these sites is dependent on the position of the fluorine substituent and the nature of the partner aromatic ring. It is found that a 2-fluorophenyl ring, when present, dominantly determines site occupation, while a 3-fluorophenyl ring has no effects that are detectably different from those of an unsubstituted phenyl ring. There is evidence for slow aromatic ring rotation within at least one of the phenyl ring interaction sites. Saturation transfer and lineshape methods provide information about the rates of interconversion of the N-phenyl groups between these sites. Line-width, spin-lattice relaxation times and fluorine-proton nuclear Overhauser effects determined at 282 and 470 MHz are reported for each system examined.

Regioselective synthesis of novel 3-allyl-2-(substituted imino)-4-phenyl-3H-thiazole and 2,2‧-(1,3-phenylene)bis(3-substituted-2-imino-4-phenyl-3H-thiazole) derivatives as antibacterial agents

NASA Astrophysics Data System (ADS)

Abbasi Shiran, Jafar; Yahyazadeh, Asieh; Mamaghani, Manouchehr; Rassa, Mehdi

2013-05-01

Several novel 3-allyl-2-(substituted imino)-4-phenyl-3H-thiazole derivatives were synthesized by the reaction of allyl-thioureas and 2-bromoacetophenone. We also report the synthesis of bis-allyl-3H thiazoles using the reaction of various isothiocyanates and 1,3-phenylenediamine. The structures of all compounds were characterized by spectral and elemental analysis. Most of the synthesized compounds exhibited efficient antibacterial activities against Salmonella enterica, Micrococcus luteus, Bacillus subtilis and Pseudomonas aeruginosa.

Synthesis, spectroscopic investigation and theoretical studies of 2-((E)-(2-(2-cyanoacetyl)hydrazono)methyl)-4-((E)-phenyldiazenyl)phenyl methyl carbonate

NASA Astrophysics Data System (ADS)

Arokiasamy, A.; Manikandan, G.; Thanikachalam, V.; Gokula Krishnan, K.

2017-04-01

Synthesis and computational optimization studies have been carried out by Hartree-Fock (HF) and Density Functional Theory (DFT-B3LYP) methods with 6-31+G(d, p) basis set for 2-((E)-(2-(2-cyanoacetyl)hydrazono)methyl)-4-((E)-phenyldiazenyl)phenyl methyl carbonate (CHPMC). The stable configuration of CHPMC was confirmed theoretically by potential energy surface scan analysis. The complete vibrational assignments were performed on the basis of total energy distribution (TED) analysis. The vibrational properties studied by IR and Raman spectroscopic data complemented by quantum chemical calculations support the formation of intramolecular hydrogen bond. Furthermore, the UV-Vis spectra are interpreted in terms of TD-DFT quantum chemical calculations. The shapes of the simulated absorption spectra are in good agreement with the experimental data. The comparison between the experimental and theoretical values of FT-IR, FT-Raman vibrational spectra, NMR (1H and 13C) and UV-Vis spectra have also been discussed.

Synthesis of new unsymmetrical 4,5-dihydroxy-2-imidazolidinones. Dynamic NMR spectroscopic study of the prototropic tautomerism in 1-(2-benzimidazolyl)-3-phenyl-4,5-dihydroxy-2-imidazolidinone.

PubMed

Ghandi, Mehdi; Olyaei, Abolfazl; Salimi, Farshid

2006-10-19

The acid-catalyzed cyclocondensation in refluxing acetonitrile of aqueous glyoxal with N-heteroaryl-N'-phenylureas 4a-f (heteroaryl = 2-thiazolyl, 2-pyrimidinyl,2-pyrazinyl, 2-pyridinyl, 3-pyridinyl and 2-benzimidazolyl) led to the formation of the corresponding 1-heteroaryl-3-phenyl-4,5-dihydroxy-2-imidazolidinones 5a-f. All the products were characterized by elemental and spectroscopic analyses. The free-energy barrier (Delta G not equal) for prototropic tautomerism in 1-(2-benzimidazolyl)-3-phenyl-4,5-dihydroxy-2-imidazolidinone (5f) was determined by dynamic NMR studies to be 81 +/- 2 KJ mol(-1).

4-(4-Methoxy­phen­yl)-1-phenyl­pyridine-2,6(1H,3H)-dione

PubMed Central

Das, Ushati; Chheda, Shardul B.; Pednekar, Suhas R.; Karambelkar, Narendra P.; Guru Row, T. N.

2009-01-01

In the title compound, C18H15NO3, the pyridine-2,6-dione ring adopts an envelope conformation. The phenyl ring lies approximately perpendicular to the mean plane of the pyridine-2,6-dione ring [dihedral angle = 81.5 (1)°], while the methoxy­phenyl ring is tilted to the same plane by a dihedral angle of 34.8 (1)°. Inter­molecular C—H⋯O inter­actions link the mol­ecules into chains along [100]. PMID:21583176

Highly chromic, proton-responsive phenyl pyrimidones.

PubMed

Dhuguru, Jyothi; Gheewala, Chirag; Kumar, N S Saleesh; Wilson, James N

2011-08-19

Aryl pyrimidones are pharmacologically relevant compounds whose optical properties have only been partially explored. We report the synthesis and optical characterization of a series of aryl- and diaryl-2(1H)-pyrimidones. The electronic transitions of these chromophores are modulated by the extent of conjugation between the pendant phenyl ring and the pyrimidone core as well as the presence of electron-donating auxochromes. Monoprotonation of the pyrimidone ring results in large hyperchromic and bathochromic shifts as well as switching of fluorescence making these phenyl pyrimidones of interest as sensory materials. © 2011 American Chemical Society

Synthesis, crystal structures, molecular docking, in vitro monoamine oxidase-B inhibitory activity of transition metal complexes with 2-{4-[bis (4-fluorophenyl)methyl]piperazin-1-yl} acetic acid

NASA Astrophysics Data System (ADS)

Yang, Dan-dan; Wang, Riu; Zhu, Jin-long; Cao, Qi-yue; Qin, Jie; Zhu, Hai-liang; Qian, Shao-song

2017-01-01

Three novel complexes, [Cu(L)2(H2O)](1), [Zn(L)2(H2O)2]·CH3OH·1.5H2O(2), and [Ni(L)2(H2O)1.8]·CH3OH·1.2H2O (3) (HL = 2-{4-[bis(4-fluorophenyl)methyl]pipera-zin-1-yl} acetic acid), were synthesized and structurally determined by single-crystal X-ray diffraction. Molecular docking study preliminarily revealed that complex 1 had potential Monoamine oxidase B inhibitory activity. All acquired compounds were tested against rat brain MAO-B in vitro. In accordance with the result of calculation, it showed complex 1 (IC50 = 1.85 ± 0.31 μM) have good inhibitory activity against MAO-B at the same micromolar concentrations with positive control Iproniazid Phosphate (IP, IC50 = 7.59 ± 1.17 μM). These results indicated that complex 1 was a potent MAO-B inhibitor.

(2E)-1-(5-Chlorothiophen-2-yl)-3-{4-[(E)-2-phenylethenyl]phenyl}prop-2-en-1-one: Synthesis, XRD, FT-IR, Raman and DFT studies.

PubMed

Parlak, Cemal; Ramasami, Ponnadurai; Kumar, Chandraju Sadolalu Chidan; Tursun, Mahir; Quah, Ching Kheng; Rhyman, Lydia; Bilge, Metin; Fun, Hoong-Kun; Chandraju, Siddegowda

2015-01-01

A novel (2E)-1-(5-chlorothiophen-2-yl)-3-{4-[(E)-2-phenylethenyl]phenyl}prop-2-en-1-one [C21H15ClOS] compound has been synthesized and its structure has been characterized by FT-IR, Raman and single-crystal X-ray diffraction techniques. The conformational isomers, optimized geometric parameters, normal mode frequencies and corresponding vibrational assignments of the compound have been examined by means of HF, MP2, BP86, BLYP, BMK, B3LYP, B3PW91, B3P86 and M06-2X functionals. Reliable vibrational assignments and molecular orbitals have been investigated by the potential energy distribution and natural bonding orbital analyses, respectively. The compound crystallizes in the triclinic space group P-1 with the cis-trans-trans form. There is a good agreement between the experimentally determined structural parameters and vibrational frequencies of the compound and those predicted theoretically using the density functional theory with the BLYP and BP86 functionals. Copyright © 2015 Elsevier B.V. All rights reserved.

21 CFR 73.3122 - 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one.

Code of Federal Regulations, 2013 CFR

2013-04-01

... 21 Food and Drugs 1 2013-04-01 2013-04-01 false 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF COLOR ADDITIVES EXEMPT FROM CERTIFICATION Medical...

21 CFR 73.3122 - 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one.

Code of Federal Regulations, 2014 CFR

2014-04-01

... 21 Food and Drugs 1 2014-04-01 2014-04-01 false 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF COLOR ADDITIVES EXEMPT FROM CERTIFICATION Medical...

21 CFR 73.3122 - 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one.

Code of Federal Regulations, 2010 CFR

2010-04-01

... 21 Food and Drugs 1 2010-04-01 2010-04-01 false 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF COLOR ADDITIVES EXEMPT FROM CERTIFICATION Medical...

21 CFR 73.3122 - 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one.

Code of Federal Regulations, 2012 CFR

2012-04-01

... 21 Food and Drugs 1 2012-04-01 2012-04-01 false 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF COLOR ADDITIVES EXEMPT FROM CERTIFICATION Medical...

21 CFR 73.3122 - 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one.

Code of Federal Regulations, 2011 CFR

2011-04-01

... 21 Food and Drugs 1 2011-04-01 2011-04-01 false 4-[(2,4-dimethylphenyl)azo]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one. 73.3122 Section 73.3122 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF COLOR ADDITIVES EXEMPT FROM CERTIFICATION Medical...

Antiestrogens and antiestrogen metabolites: preparation of tritium-labeled (+-)-cis-3-(p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)-phenoxyl)-1,2-propanediol (U23469) and characterization and synthesis of a biologically important metabolite

DOE Office of Scientific and Technical Information (OSTI.GOV)

Tatee, T.; Carlson, K.E.; Katzenellenbogen, J.A.

1979-12-01

The Upjohn antiestrogen (+-)-cis-3-(p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)-phenoxyl)-1,2-propanediol (2b, U 23469) has been prepared in tritium-labeled form by reduction of an unsaturated dihydronaphthalene precursor with carrier-free tritium gas over a palladium catalyst followed by alkylation with 3-iodo-1,2-propanediol. After extensive chromatographic purification, the final material was obtained with a specific activity of 13 Ci/mmol and a radiochemical purity of 94%. In vivo studies with immature rats show that (3H)2b is slowly converted to a more polar metabolite that is selectively accumulated in the nuclear fraction of the uterus where it is bound to the estrogen receptor. Chromatographic comparisons indicate that this metabolite is the demethylatedmore » analogue 2c, a compound that has an affinity for estrogen receptor more than 300 times greater than that of 2b. These studies suggest that the demethylated analogue 2c may be a biologically important metabolite of 2b that is involved in the action of this antiestrogen.« less

Synthesis, spectral characterization and antimicrobial studies of nano-sized oxovanadium(IV) complexes with Schiff bases derived from 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazole and indoline-2,3-dione.

PubMed

Sahani, M K; Yadava, U; Pandey, O P; Sengupta, S K

2014-05-05

A new class of oxovanadium(IV) complexes with Schiff bases derived by the condensation of 5-(phenyl/substituted phenyl)-2-hydrazino-1,3,4-thiadiazoles and indoline-2,3-dione have been prepared in ethanol in the presence of sodium acetate. Micro-analytical data, magnetic susceptibility, UV-Vis, IR, EPR and XRD spectral techniques were used to confirm the structures. Electronic absorption spectra of the complexes suggest a square-pyramidal geometry. The oxovanadium(IV) complexes have monoclinic crystal system and particle sizes were found to be in the range 18.0 nm to 24.0 nm (nano-size). In vitro antifungal activity of synthesized compounds was determined against fungi Aspergillus niger, Colletotrichum falcatum and Colletotrichum pallescence and in vitro antibacterial activity was determined by screening the compounds against Gram-negative (Escherichia coli and Salmonella typhi) and Gram-positive (Staphylococcus aureus and Bacillus subtilis) bacterial strains. The oxovanadium(IV) complexes have higher antimicrobial effect than free ligands. Copyright © 2014 Elsevier B.V. All rights reserved.

DFT and PCM-TD-DFT investigation of the electronic structures and spectra of 5-(3-phenyl-2-propenylidene)-2-thioxo-4-thiazolidinone derivatives

NASA Astrophysics Data System (ADS)

El-Taher, Sabry; Metwaly, Mohamed

2017-04-01

UV-Visible absorption spectra of 5-(3-phenyl-2-propenylidene)-2-thioxo-4-thiazolidinones (5pR-PPTT, R = H, CH3, CH3O, and N(CH3)2) were measured in different solvents and investigated using the theoretical PCM-TD-DFT scheme. A benchmark evaluation against experimental results on the accuracy of different DFT functionals has been performed. The best agreement with X-ray data is achieved by using the long-range corrected LC-wPBE functional, while the PBE0 functional provided the most accurate λmax for the studied compounds. The thionic forms of the ZE isomers of the studied compounds are found to be the most stable tautomers. The assignation debate of the second absorption band of rhodanine [2-thioxo-4-thiazolidinone (Rd)] has been solved by confirming on its π-π∗ nature. It was found that the expansion of the π-conjugation system at position 5 of Rd ring leads to significant bathochromic shift. The CT lengths (Δr) and dipole moment change (ΔμCT) indices showed that the charge transfer character of the electronic transitions is directly proportional to the electron-releasing strength of substituted phenyl ring. It was concluded that the red shifting of the maximum absorption is mainly regulated by the solvent polarizability and much less by solvent polarity.

Exploration of chlorinated thienyl chalcones: A new class of monoamine oxidase-B inhibitors.

PubMed

Mathew, Bijo; Haridas, Abitha; Uçar, Gülberk; Baysal, Ipek; Adeniyi, Adebayo A; Soliman, Mahmoud E S; Joy, Monu; Mathew, Githa Elizabeth; Lakshmanan, Baskar; Jayaprakash, Venkatesan

2016-10-01

Chalcone has been reported to be a valid scaffold for the design of monoamine oxidase (MAO) inhibitors. This scenario has amplified the momentum for the discovery of heteroaryl based chalcone MAO inhibitors. In the present study, we have synthesized a series of eleven chlorinated thienyl chalcone derivatives substituted with a different functional groups at the para- position on the ring B and investigated for their ability to inhibit human MAO-A and -B. With the exception of compound (2E)-1-(4-chlorocyclopenta-1,3-dien-1-yl)-3-(4-nitrophenyl)prop-2-en-1-one (TC7), which was a selective MAO-A inhibitor, all the other derivatives inhibited hMAO-B potently and selectively with competitive mode of inhibition. The most potent compound (2E)-1-(4-chlorocyclopenta-1,3-dien-1-yl)-3-(4-ethylphenyl)prop-2-en-1-one (TC6) was found to be the best activity and higher selectivity towards hMAO-B with Ki and SI values of 0.31±0.02μM and 16.84, respectively. All the compounds presented in the current study are completely non-toxic with 74-88% viable cells to hepatic cells at 100μM concentration. Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.2 and Amber 14 to understand the molecular level interaction and energy relation of MAO isoforms with selective MAO-B inhibitor TC6. Copyright © 2016 Elsevier B.V. All rights reserved.

N-(4-Meth-oxy-phen-yl)-6-methyl-2-phenyl-5-{[4-(tri-fluoro-meth-yl)anilino]meth-yl}pyrimidin-4-amine.

PubMed

Cieplik, Jerzy; Pluta, Janusz; Bryndal, Iwona; Lis, Tadeusz

2013-11-27

The title compound, C26H23F3N4O, crystallizes with two symmetry-independent mol-ecules in the asymmetric unit, denoted A and B, which differ mainly in the rotation of the meth-oxy-phenyl ring. The -CF3 group of mol-ecule B is disordered by rotation, with the F atoms split over two sets of sites; the occupancy factor for the major component is 0.853 (4). The dihedral angles between the pyrimidine ring and the attached phenyl, meth-oxy-phenyl and tri-fluoro-methyl-phenyl rings are 8.1 (2), 37.5 (2) and 70.7 (2)°, respectively, in mol-ecule A, and 9.3 (2), 5.3 (2) and 79.7 (2)° in mol-ecule B. An intra-molecular N-H⋯N hydrogen bond occurs in each mol-ecule. In the crystal, two crystallographically independent mol-ecules associate into a dimer via a pair of N-H⋯N hydrogen bonds, with a resulting R 2 (2)(12) ring motif and π-π stacking inter-actions [centroid-centroid distance = 3.517 (4) Å] between the pyrimidine rings. For the A mol-ecules, there are inter-molecular C-H⋯O hydrogen bonds between an aryl C atom of meth-oxy-phenyl ring and a meth-oxy O atom of an adjacent mol-ecule. A similar inter-action is lacking in the B mol-ecules.

Overview of the TREC 2009 Chemical IR Track

DTIC Science & Technology

2009-11-01

several classes have been identified. 3 methods for controlling molecular weight of polyhydroxyalkanoate organic, high molecular weight We are a group of...researchers in an university/company. We want to start a project and, before starting, we want more informations about polyhydroxyalkanoate and about...methods for controlling molecular weight of polyhydroxyalkanoate constituted of units containing residue of phenyl-, thienyl-, or cyclohexyl-structure

(E)-3-Methyl-2,6-di­phenyl­piperidin-4-one O-(3-methyl­benzo­yl)oxime

PubMed Central

Kathiravan, V.; Krishnan, K. Gokula; Mohandas, T.; Thanikachalam, V.; Sakthivel, P.

2014-01-01

In the title compound, C26H26N2O2, the piperidine ring exhibits a chair conformation. The phenyl rings are attached to the central heterocycle in an equatorial position. The dihedral angle between the planes of the phenyl rings is 57.58 (8)°. In the crystal, C—H⋯O inter­actions connect the mol­ecules into zigzag chains along [001]. PMID:25249925

Higher coordinate gold(I) complexes with the weak Lewis base tri(4-fluorophenyl) phosphine. Synthesis, structural, luminescence, and DFT studies

NASA Astrophysics Data System (ADS)

Agbeworvi, George; Assefa, Zerihun; Sykora, Richard E.; Taylor, Jared; Crawford, Carlos

2016-03-01

The structures and spectroscopic properties of two high coordinate gold(I) phosphine complexes with the TFFPP=tri(4-fluorophenyl)phosphine ligand are reported. Synthesis in a 1:3 metal to ligand ratio provided the compound [AuCl(TFFPP)3] (2) that crystallize in the P 1 bar space group, where the asymmetric unit consists of three independent molecules. In all three sites, two sets of bond angles display distinctly different ranges. The three P-Au-P angles have average values of 117.92°, 117.57°, and 114.78° for sites A, B, and C, with the corresponding P-Au-Cl angles of 98.31°, 99.05°, and 103.38°, respectively. The chloride ion coordinates as the fourth ligand, at the corresponding Au-Cl distance of 2.7337, 2.6825, and 2.6951 Å for the three sites. This distance is longer by 0.40-0.45 Å than the Au-Cl distance found in the mono TFFPP complex 1 (2.285 Å) indicating a weakening of the Au-Cl interaction as the coordination number increases. In compound 3, [Au(TFFPP)3]Cl·½CH2Cl2·H2O, the structure consists of three phosphine ligands bound to the gold(I) atom, but the Cl- exists as uncoordinated counter anion. The structural differences observed in the two complexes are attributable to crystal-packing effects caused by the introduction of H-bonding as well as enhanced intra and inter-molecular π-interaction in 3. The photoluminescence of the complexes compared with that of the ligand show ligand centered emission perturbed by the metal coordination. Theoretical DFT studies conducted on these complexes supports assignments of the electronic transitions observed in these systems.

Infrared Spectra of M^+(2-AMINO-1-PHENYL ETHANOL)(H_2O)_{n=0-2}Ar (M=Na, K)

NASA Astrophysics Data System (ADS)

Nicely, Amy L.; Lisy, James M.

2009-06-01

A balance of competing electrostatic and hydrogen bonding interactions directs the structure of hydrated gas-phase cluster ions. Because of this, a biologically relevant model of cluster structures should include the effects of surrounding water molecules and metal ions such as sodium and potassium, which are found in high concentrations in the bloodstream. The molecule 2-amino-1-phenyl ethanol (APE) serves as a model for the neurotransmitters ephedrine and adrenaline. The neutral APE molecule contains an internal hydrogen bond between the amino and hydroxyl groups. In the M^+(APE) complex, the cation can either interrupt the internal hydrogen bond or position itself above the phenyl group, leaving the internal hydrogen bond intact. The former is preferred based on DFT calculations (B3LYP/6-31+G*) for both K^+ and Na^+ across the entire range from 0-400K, but infrared photodissociation (IRPD) spectra indicate a preference for the latter configuration at low temperatures. The IRPD spectra of M^+(H_2O)_{n=1-2} and M^+(H_2O)_{n=0-2}Ar (M=Na, K) will be presented along with parallel DFT and thermodynamics calculations to assist with the identification of the isomers present in each experiment.

40 CFR 721.10409 - Poly(oxyalkylenediyl), .alpha.-[[[methyl-3-[[[(polyfluoroalkyl)oxy]carbonyl] amino]phenyl]amino...

Code of Federal Regulations, 2014 CFR

2014-07-01

....-[[[methyl-3-[[[(polyfluoroalkyl)oxy]carbonyl] amino]phenyl]amino]carbonyl]- .omega.-methoxy-(generic). 721....-[[[methyl-3-[[[(polyfluoroalkyl) oxy]carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (PMN P-11-217... Substances § 721.10409 Poly(oxyalkylenediyl), .alpha.-[[[methyl-3-[[[(polyfluoroalkyl)oxy]carbonyl] amino...

40 CFR 721.10409 - Poly(oxyalkylenediyl), .alpha.-[[[methyl-3-[[[(polyfluoroalkyl) oxy]carbonyl]amino]phenyl]amino...

Code of Federal Regulations, 2012 CFR

2012-07-01

....-[[[methyl-3-[[[(polyfluoroalkyl) oxy]carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (generic). 721....-[[[methyl-3-[[[(polyfluoroalkyl) oxy]carbonyl]amino]phenyl]amino] carbonyl]-.omega.-methoxy- (PMN P-11-217... Substances § 721.10409 Poly(oxyalkylenediyl), .alpha.-[[[methyl-3-[[[(polyfluoroalkyl) oxy]carbonyl]amino...

Quantum-chemical, NMR and X-ray diffraction studies on (+/-)-1-[3,4-(methylenedioxy)phenyl]-2-methylaminopropane.

PubMed

Zapata-Torres, Gerald; Cassels, Bruce K; Parra-Mouchet, Julia; Mascarenhas, Yvonne P; Ellena, Javier; De Araujo, A S

2008-06-01

Time-averaged conformations of (+/-)-1-[3,4-(methylenedioxy)phenyl]-2-methylaminopropane hydrochloride (MDMA, "ecstasy") in D(2)O, and of its free base and trifluoroacetate in CDCl(3), were deduced from their (1)H NMR spectra and used to calculate their conformer distribution. Their rotational potential energy surface (PES) was calculated at the RHF/6-31G(d,p), B3LYP/6-31G(d,p), B3LYP/cc-pVDZ and AM1 levels. Solvent effects were evaluated using the polarizable continuum model. The NMR and theoretical studies showed that, in the free base, the N-methyl group and the ring are preferentially trans. This preference is stronger in the salts and corresponds to the X-ray structure of the hydrochloride. However, the energy barriers separating these forms are very low. The X-ray diffraction crystal structures of the anhydrous salt and its monohydrate differed mainly in the trans or cis relationship of the N-methyl group to the alpha-methyl, although these two forms interconvert freely in solution.

Intramolecular cyclization of N-phenyl N'(2-chloroethyl)ureas leads to active N-phenyl-4,5-dihydrooxazol-2-amines alkylating β-tubulin Glu198 and prohibitin Asp40.

PubMed

Trzeciakiewicz, Anna; Fortin, Sébastien; Moreau, Emmanuel; C-Gaudreault, René; Lacroix, Jacques; Chambon, Christophe; Communal, Yves; Chezal, Jean-Michel; Miot-Noirault, Elisabeth; Bouchon, Bernadette; Degoul, Françoise

2011-05-01

The cyclization of anticancer drugs into active intermediates has been reported mainly for DNA alkylating molecules including nitrosoureas. We previously defined the original cytotoxic mechanism of anticancerous N-phenyl-N'-(2-chloroethyl)ureas (CEUs) that involves their reactivity towards cellular proteins and not against DNA; two CEU subsets have been shown to alkylate β-tubulin and prohibitin leading to inhibition of cell proliferation by G₂/M or G₁/S cell cycle arrest. In this study, we demonstrated that cyclic derivatives of CEUs, N-phenyl-4,5-dihydrooxazol-2-amines (Oxas) are two- to threefold more active than CEUs and share the same cytotoxic properties in B16F0 melanoma cells. Moreover, the CEU original covalent binding by an ester linkage on β-tubulin Glu198 and prohibitin Asp40 was maintained with Oxas. Surprisingly, we observed that Oxas were spontaneously formed from CEUs in the cell culture medium and were also detected within the cells. Our results suggest that the intramolecular cyclization of CEUs leads to active Oxas that should then be considered as the key intermediates for protein alkylation. These results will be useful for the design of new prodrugs for cancer chemotherapy. Copyright © 2011 Elsevier Inc. All rights reserved.

Ultrasound-assisted synthesis of novel 4-(2-phenyl-1,2,3-triazol-4-yl)-3,4-dihydropyrimidin-(1H)-(thio)ones catalyzed by Sm(ClO(4))(3).

PubMed

Liu, Chen-Jiang; Wang, Ji-De

2010-03-24

An efficient synthesis of novel 4-(2-phenyl-1,2,3-triazol-4-yl)-3,4-dihydro-pyrimidin-2(1H)-(thio)ones from 1,3-dicarbonyl compounds, 2-phenyl-1,2,3-triazole-4-carbaldehyde and urea or thiourea under ultrasound irradiation and using samarium perchlorate as catalyst is described. Compared with conventional methods, the main advantages of the present methodology are milder conditions, shorter reaction times and higher yields.

Synthesis of 2-{(5-phenyl-1,3,4-Oxadiazol-2-yl)sulfanyl}-N-substituted acetamides as potential antimicrobial and hemolytic agents.

PubMed

Rehman, Aziz-ur; Abbasi, Muhammad Athar; Siddiqui, Sabahat Zahra; Ahmad, Irshad; Shahid, Muhammad; Subhani, Zinayyera

2016-05-01

A new series of N-substituted derivatives of 2-{(5-phenyl-1,3,4-Oxadiazol-2-yl)sulfanyl}acetamides was synthesized. The synthesis was carried out by converting benzoic acid (1) into ethyl benzoate (2), benzohydrazide (3) and then 5-pheny-1,3,4-Oxadiazol-2-thiol (4) step by st0ep. The target compounds 6a-p were synthesized by reaction of compound 4 with equimolar ratios of different N-alkyl/aryl substituted 2-bromoacetamide (5a-p) in the presence of DMF and sodium hydride (NaH). The spectral (EI-MS, IR, (1)H-NMR) characterization of all the synthesized compounds reveal their successful synthesis. The compounds were also screened for antimicrobial & hemolytic activity and most of them were found to be active against the selected microbial species at variable extent relative to reference standards. But 6h was the most active against the selected panel of microbes. This series showed less toxicity and may be considered for further biological screening and application trial except 6m, possessing higher cytotoxicity.

Infrared, Raman and density functional characterization and structural study of 2-Nitro-2-phenyl-propane-1,3-diol

NASA Astrophysics Data System (ADS)

Kaya, Mehmet Fatih; Bağlayan, Özge; Kaya, Esma Güneş; Alver, Özgür

2017-12-01

Nitro compound and nitro derivatives are industrially important to produce rubber and agricultural chemicals. In this study, one of the promising derivatives of nitro compound 2-Nitro-2-phenyl-propane-1,3-diol (2NPP) is examined in detail. FT-Infrared and dispersive Raman spectra of 2NPP (C9H11NO4) were respectively recorded in 4000-10 cm-1 and 4000-100 cm-1. The bond distances and angles, conformational distributions, vibrational frequencies and the assignment of each mode, some thermodynamic parameters and reactivity descriptors: total energy, hardness, chemical potential, electrophilicity index, electronegativity, frontier orbitals energy gap of 2NPP were investigated by using DFT/B3LYP method with 6-31++G (d,p) basis set. In order to locate the global minimum on the potential energy surface of 2NPP, a beforehand conformational examinations were carried out using Spartan 10 along with semi-emprical PM6 method. The results of conformational analyses showed that there are five possible conformations having energies under 2 kcal/mol. Comparison of the theoretical and experimental results clearly indicates that density functional hybrid B3LYP/6-31++G (d,p) level of theory can be used to predict vibrational frequencies and structural parameters of 2NPP. Further, C1 geometry is considered to be the global minimum conformation of 2NPP.

Enzymatic synthesis of S-phenyl-L-cysteine from keratin hydrolysis industries wastewater with tryptophan synthase.

PubMed

Xu, Lisheng; Wang, Zhiyuan; Mao, Pingting; Liu, Junzhong; Zhang, Hongjuan; Liu, Qian; Jiao, Qing-Cai

2013-04-01

An economical method for production of S-phenyl-L-cysteine from keratin acid hydrolysis wastewater (KHW) containing L-serine was developed by recombinant tryptophan synthase. This study provides us with an alternative KHW utilization strategy to synthesize S-phenyl-L-cysteine. Tryptophan synthase could efficiently convert L-serine contained in KHW to S-phenyl-L-cysteine at pH 9.0, 40°C and Trion X-100 of 0.02%. In a scale up study, L-serine conversion rate reach 97.1% with a final S-phenyl-L-cysteine concentration of 38.6 g l(-1). Copyright © 2013 Elsevier Ltd. All rights reserved.

Molecular structure, FT IR, NMR, UV, NBO and HOMO-LUMO of 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile by DFT/B3LYP and PBEPBE methods with LanL2DZ and 6-311++G(d,2p) basis sets.

PubMed

Khajehzadeh, Mostafa; Moghadam, Majid

2017-06-05

Structural and molecular properties of antidepressants 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile were examined using quantum mechanics of Density Functional Theory (DFT)/B3LYP and PBEPBE methods with 6-311++G(d,2p) and LanL2DZ basis sets to study the therapeutic properties of the drug. For this, the structure of desired material was optimized by the computer calculation method and with the use of powerful Gaussian 09 software. Then the lowest energy value and the bond length, bond angle and dihedral angle between its constituent atoms in the crystal structure of the desired material were measured from the optimized values. Then the amount of positive and negative charges, polarizability and dipole moment of its atoms using Mulliken charge and Natural atomic charges, DFT/B3LYP and PBEPBE methods with 6-311++G(d,2p) and LanL2DZ basis sets were determined and the results were compared with each other for individual atoms and by mentioned methods. Also the type of stretching vibrations and bending vibrations between the constituent atoms of the molecule were specified using mentioned computational methods and FT IR vibrational spectra. The experimental spectrum of this material was taken to determine the functional groups and the computational and experimental values were compared to each other and Nuclear Magnetic Resonance (NMR) was used to specify the isomer shift between the carbons and protons in the presence of polar and nonpolar solvents. Also Natural Bond Orbital (NBO) was used to determine the type of electron transfers in σ→σ∗ and π→π∗ and LP(1)→σ∗ and LP(2)→σ∗ and the amount of hardness and softness in molecule was determined using the difference between ionization energy and electron affinity energy in constituent atoms of that molecule in the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and in the presence of solvents H 2 O, CH 3 CN and C 6 H 12

Molecular structure, FT IR, NMR, UV, NBO and HOMO-LUMO of 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile by DFT/B3LYP and PBEPBE methods with LanL2DZ and 6-311 ++G(d,2p) basis sets

NASA Astrophysics Data System (ADS)

Khajehzadeh, Mostafa; Moghadam, Majid

2017-06-01

Structural and molecular properties of antidepressants 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile were examined using quantum mechanics of Density Functional Theory (DFT)/B3LYP and PBEPBE methods with 6-311 ++ G(d,2p) and LanL2DZ basis sets to study the therapeutic properties of the drug. For this, the structure of desired material was optimized by the computer calculation method and with the use of powerful Gaussian 09 software. Then the lowest energy value and the bond length, bond angle and dihedral angle between its constituent atoms in the crystal structure of the desired material were measured from the optimized values. Then the amount of positive and negative charges, polarizability and dipole moment of its atoms using Mulliken charge and Natural atomic charges, DFT/B3LYP and PBEPBE methods with 6-311 ++ G(d,2p) and LanL2DZ basis sets were determined and the results were compared with each other for individual atoms and by mentioned methods. Also the type of stretching vibrations and bending vibrations between the constituent atoms of the molecule were specified using mentioned computational methods and FT IR vibrational spectra. The experimental spectrum of this material was taken to determine the functional groups and the computational and experimental values were compared to each other and Nuclear Magnetic Resonance (NMR) was used to specify the isomer shift between the carbons and protons in the presence of polar and nonpolar solvents. Also Natural Bond Orbital (NBO) was used to determine the type of electron transfers in σ → σ ∗ and π → π ∗ and LP(1) → σ ∗ and LP(2) → σ ∗ and the amount of hardness and softness in molecule was determined using the difference between ionization energy and electron affinity energy in constituent atoms of that molecule in the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and in the presence of solvents H2O, CH3CN

Solution-Processable Low-Molecular Weight Extended Arylacetylenes: Versatile p-Type Semiconductors for Field-Effect Transistors and Bulk Heterojunction Solar Cells

DOE Office of Scientific and Technical Information (OSTI.GOV)

Silvestri, Fabio; Marrocchi, Assunta; Seri, Mirko

2010-04-08

We report the synthesis and characterization of a series of five extended arylacetylenes, 9,10-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-anthracene (A-P6t, 1), 9,10-bis-[(p-{[m,p-bis(hexyloxy) phenyl]ethynyl}phenyl)ethynyl]-anthracene (PA-P6t, 2), 4,7-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazole (BTZ-P6t, 5), 4,7-bis(5-{[m,p-bis(hexyloxy)phenyl]ethynyl}thien-2-yl)-2,1,3-benzothiadiazole (TBTZ-P6t, 6), and 7,7'-({[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazol-4,4'-ethynyl)-2,5-thiophene (BTZT-P6t, 7), and two arylvinylenes, 9,10-bis-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}-anthracene (A-P6d, 3), 9,10-bis-[(E)-(p-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}phenyl)vinyl]-anthracene (PA-P6d, 4). Trends in optical absorption spectra and electrochemical redox processes are first described. Next, the thin-film microstructures and morphologies of films deposited from solution under various conditions are investigated, and organic field-effect transistors (OFETs) and bulk heterojunction photovoltaic (OPV) cells fabricated. We find that substituting acetylenic for olefinic linkers on the molecular cores significantly enhances device performance. OFET measurements reveal that allmore » seven of the semiconductors are FET-active and, depending on the backbone architecture, the arylacetylenes exhibit good p-type mobilities (μ up to ~0.1 cm 2 V -1 s -1) when optimum film microstructural order is achieved. OPV cells using [6,6]-phenyl C 61-butyric acid methyl ester (PCBM) as the electron acceptor exhibit power conversion efficiencies (PCEs) up to 1.3% under a simulated AM 1.5 solar irradiation of 100 mW/cm 2. These results demonstrate that arylacetylenes are promising hole-transport materials for p-channel OFETs and promising donors for organic solar cells applications. A direct correlation between OFET arylacetylene hole mobility and OPV performance is identified and analyzed.« less

Complexes of dichloro[2-(dimethylaminomethyl)phenyl-C1,N]gold(III), [Au(damp-C1,N)Cl2], with formylferrocene thiosemicarbazones: synthesis, structure and cytotoxicity.

PubMed

Casas, José S; Castaño, María V; Cifuentes, María C; García-Monteagudo, Juán C; Sánchez, Agustín; Sordo, José; Abram, Ulrich

2004-06-01

Dichloro[2-(dimethylaminomethyl)phenyl- phenyl-C1,N]gold(III), [Au(damp-C1,N)Cl2], reacts with the formylferrocene thiosemicarbazones derived from 4-methyl-, 4-phenyl-, 4-ethyl- and 4,4-dimethyl-3-thiosemicarbazides, HFcTSC, to give complexes of general formula [Au(Hdamp-1C)Cl(FcTSC)]Cl. These complexes were isolated and characterized by elemental analysis, mass spectrometry and IR, 1H NMR and (13)C NMR spectroscopy. In some cases, cyclic voltammetric studies were carried out and these showed that the complexation of gold affects the redox behaviour of the ferrocene unit. The in vitro antitumor activity against the HeLa cell line was also determined for the more soluble complexes. The IC(50) values were found to be higher than that of cisplatin but the maximum antiproliferative activity was similar.

Molecular structure and ring tunneling of phenyl formate as observed by microwave spectroscopy and quantum chemistry

NASA Astrophysics Data System (ADS)

Ferres, Lynn; Mouhib, Halima; Stahl, Wolfgang; Schwell, Martin; Nguyen, Ha Vinh Lam

2017-07-01

Phenyl formate has been investigated by molecular jet Fourier-transform microwave spectroscopy in the frequency range from 2 to 26.5 GHz. Quantum chemical calculations at the MP2/6-311++G(d,p) level of theory indicate that this molecule does not have a plane of symmetry at equilibrium, and that the phenyl ring performs a large amplitude tunneling motion from one side of the Cs configuration to the other. The tilt angle of the ring out of the Hsbnd (Cdbnd O)O plane is ±70° and the calculated tunneling barrier is only 28 cm-1. The two lowest torsional states vt = 0 and 1 are assigned in the experimental spectrum and fitted using the program SPFIT/SPCAT. The Coriolis splitting ΔE between these states is 46.2231(25) GHz, very close to the value of 48.24 GHz calculated using a simple two-top torsional Hamiltonian of the formate group and the phenyl ring.

Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids.

PubMed

Huang, Ling; Su, Tao; Shan, Wenjun; Luo, Zonghua; Sun, Yang; He, Feng; Li, Xingshu

2012-05-01

A series of berberine-phenyl-benzoheterocyclic (26-29) and tacrine-phenyl-benzoheterocyclic hybrids (44-46) were synthesised and evaluated as multifunctional anti-Alzheimer's disease agents. Compound 44b, tacrine linked with phenyl-benzothiazole by 3-carbon spacers, was the most potent AChE inhibitor with an IC(50) value of 0.017 μM. This compound demonstrated similar Aβ aggregation inhibitory activity with cucurmin (51.8% vs 52.1% at 20 μM, respectively), indicating that this hybrid is an excellent multifunctional drug candidate for AD. Copyright © 2012 Elsevier Ltd. All rights reserved.

A facile iodine(III)-mediated synthesis of 3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridines via oxidation of 2-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)-1-(pyridin-2-yl)hydrazines and their antimicrobial evaluations

PubMed Central

2011-01-01

Background Fused heterocyclic 1,2,4-triazoles have acquired much importance because of their interesting biological properties. Although a number of methods have been reported in the literature which includes oxidation with phosphorus oxychloride, lead tetraacetate, bromine, etc., hypervalent iodine reagents have emerged as reagents of choice for various synthetically useful transformations due to their low toxicity, ready availability and ease of handling. Results A series of new 3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridines 4 has been conveniently synthesized by oxidative cyclization of 2-(3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)-1-(pyridin-2-yl)hydrazines 3 promoted with iodobenzene diacetate under mild conditions (up to 90% isolated yields). All the new compounds were tested in vitro for their antimicrobial activity. Conclusions Iodine(III)-mediated oxidative approach has offered an easy access to new 3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridines 4. The antibacterial and antifungal activities of newly synthesized compounds have proved them potent antimicrobial agents. PMID:22373059

Electronic Structure and Absorption Spectra of Sodium 2-Hydroxy-5-({2-Methoxy-4[(4-Sulfophenyl)Diazenyl]Phenyl}Diazenyl)Benzoate

NASA Astrophysics Data System (ADS)

Almodarresiyeh, H. A.; Shahab, S. N.; Zelenkovsky, V. M.; Agabekov, V. E.

2014-03-01

The electronic structure and geometry of the synthesized azodye sodium 2-hydroxy-5-({2-methoxy-4[(4-sulfophenyl) diazenyl]phenyl}diazenyl)benzoate (M12) were calculated theoretically by an ab initio Hartree-Fock method in basis set 6-31G. The nature of absorption bands in the visible and near-UV spectral regions was interpreted.

Highly selective and sensitive fluorogenic ferric probes based on aggregation-enhanced emission with - SiMe3 substituted polybenzene

NASA Astrophysics Data System (ADS)

Wang, Xuefeng; Wang, Hua; Jiang, Qin; Lee, Yong-Ill; Feng, Shengyu; Liu, Hong-Guo

2018-01-01

In this study, thiophene was linked to polybenzene to generate novel fluorescent probes, namely 3,4-diphenyl-2,5-di(2-thienyl)phenyl-trimethylsilane (DPTB-TMS) with a - SiMe3 substituent and 3,4-diphenyl-2,5-di(2-thienyl)phenyl (DPTB) without the - SiMe3 substituent, respectively. Both of the two compounds exhibit aggregation-enhanced emission (AEE) properties in tetrahydrofuran/water mixtures due to restricted intramolecular rotation of the peripheral groups, which make the two compounds good candidates for the detection of Fe3 + ions in aqueous-based solutions. The fluorescence intensity of the two compounds decreases immediately and obviously upon addition of a trace amount of Fe3 +, and decreases continuously as the amount of Fe3 + increases. The fluorescence was quenched to 92% of its initial intensity when the amount of Fe3 + ions reached 6 μmol for DPTB-TMS and to 80% for DPTB in the systems, indicating that the compound with the - SiMe3 group is a more effective probe. The detection limit was found to be 1.17 μM (65 ppb). The detection mechanism is proposed to be static quenching. DPTB-TMS is highly efficient for the detection of ferric ions even in the presence of other metal ions. In addition, the method is also successfully applied to the detection of ferric ions in water, blood serum, or solid films. This indicates that these polybenzene compounds can be applied as low-cost, high selectivity, and high efficiency Fe3 + probes in water or in clinical applications.

Substituted piperazines as nootropic agents: 2- or 3-phenyl derivatives structurally related to the cognition-enhancer DM235.

PubMed

Guandalini, Luca; Martino, Maria Vittoria; Di Cesare Mannelli, Lorenzo; Bartolucci, Gianluca; Melani, Fabrizio; Malik, Ruchi; Dei, Silvia; Floriddia, Elisa; Manetti, Dina; Orlandi, Francesca; Teodori, Elisabetta; Ghelardini, Carla; Romanelli, Maria Novella

2015-04-15

A series of 2-phenyl- or 3-phenyl piperazines, structurally related to DM235 and DM232, two potent nootropic agents, have been prepared and tested in the mouse passive-avoidance test, to assess their ability to revert scopolamine-induced amnesia. Although the newly synthesized molecules were less potent than the parent compounds, some useful information has been obtained from structure-activity relationships. A small but significant enantioselectivity has been found for the most potent compound 5a. Copyright © 2015 Elsevier Ltd. All rights reserved.

Phenyl thiazolyl urea and carbamate derivatives as new inhibitors of bacterial cell-wall biosynthesis.

PubMed

Francisco, Gerardo D; Li, Zhong; Albright, J Donald; Eudy, Nancy H; Katz, Alan H; Petersen, Peter J; Labthavikul, Pornpen; Singh, Guy; Yang, Youjun; Rasmussen, Beth A; Lin, Yang-I; Mansour, Tarek S

2004-01-05

Over 50 phenyl thiazolyl urea and carbamate derivatives were synthesized for evaluation as new inhibitors of bacterial cell-wall biosynthesis. Many of them demonstrated good activity against MurA and MurB and gram-positive bacteria including MRSA, VRE and PRSP. 3,4-Difluorophenyl 5-cyanothiazolylurea (3p) with clog P of 2.64 demonstrated antibacterial activity against both gram-positive and gram-negative bacteria.

Discovery and Optimization of 4-(8-(3-Fluorophenyl)-1,7-naphthyridin-6-yl)transcyclohexanecarboxylic Acid, an Improved PDE4 Inhibitor for the Treatment of Chronic Obstructive Pulmonary Disease (COPD).

PubMed

Press, Neil J; Taylor, Roger J; Fullerton, Joseph D; Tranter, Pamela; McCarthy, Clive; Keller, Thomas H; Arnold, Nicola; Beer, David; Brown, Lyndon; Cheung, Robert; Christie, Julie; Denholm, Alastair; Haberthuer, Sandra; Hatto, Julia D I; Keenan, Mark; Mercer, Mark K; Oakman, Helen; Sahri, Helene; Tuffnell, Andrew R; Tweed, Morris; Trifilieff, Alexandre

2015-09-10

Herein we describe the optimization of a series of PDE4 inhibitors, with special focus on solubility and pharamcokinetics, to clinical compound 2, 4-(8-(3-fluorophenyl)-1,7-naphthyridin-6-yl)transcyclohexanecarboxylic acid. Although compound 2 produces emesis in humans when given as a single dose, its exemplary pharmacokinetic properties enabled a novel dosing regime comprising multiple escalating doses and the resultant achievement of high plasma drug levels without associated nausea or emesis.

Preparation and characterization of 5-(4-hydroxy-3-nitrobenzyl)-3-phenyl-2-thiohydantoin, the phenylthiohydantoin derivative of 3-nitrotyrosine.

PubMed

Lilova, A; Kleinschmidt, T; Nedkov, P; Braunitzer, G

1986-10-01

The phenylthiocarbamoyl derivative of 3-nitrotyrosine was synthesized according to the known Edman method and then converted to its phenylthiohydantoin derivative [5-(4-hydroxy-3-nitrobenzyl)-3-phenyl-2-thiohydantion] by incubation in 0.5M HCl for 24 h at room temperature. After drying over P2O5 the chromatographically pure substance could be obtained by double recrystallization from hot acetic acid. It could be established that a shorter incubation time leads to an incomplete conversion and higher temperatures cause polymerization of the product. The compounds could be characterized by thin-layer and high-performance liquid chromatography, melting point, elemental analysis as well as NMR- and absorption spectroscopy.

Synthesis and properties of photochromic biindenylidenedione derivatives containing thiophene groups, and new insights into the reaction of 2,2‧-biindanylidene-1,1‧,3,3‧-tetraone with Grignard reagent

NASA Astrophysics Data System (ADS)

Liu, Juyan; Han, Jie; Song, Zhiyi; Wei, Yongheng; Pang, Meili; Meng, Jiben

2008-11-01

Three indenone derivatives ( 1: 2-[3'-hydroxy-3'-(2-thienyl)indanone-2'-yl]-3-(2-thienyl)indenone; 2: trans- anti-3,3'-(2-thienyl)-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'-dione and 3: trans- syn-3,3'-(2-thienyl)-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'-dione) were obtained in a one-pot reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with 2-thienylmagnesium bromide. Their structures were characterized by means of IR, 1H NMR, MS, elemental analysis, and X-ray crystallography. The photochromic and photo-induced radical behaviors of these compounds were investigated by means of solid UV-vis spectroscopy and electron spin resonance (ESR) spectroscopy. The results show that compounds 2 and 3 exhibit photochromism in the solid state, whereas compound 1 does not. The relationship between the crystal structures and photochemical properties is also discussed. Based on the formation and product distribution of compounds 1, 2, and 3, a plausible pathway is suggested for the reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with 2-thienylmagnesium bromide. The findings obtained in this study also provide new insights into the addition-oxidation mechanism for the reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with Grignard reagent.

Halonium ion-assisted deiodination of styrene-based vicinal iodohydrins followed by rearrangement through phenyl migration.

PubMed

Agrawal, Manoj K; Ghosh, Pushpito K

2009-10-16

Acid activation of bromate/bromide couple at 0-10 degrees C was found to trigger the deiodination of styrene-based vicinal iodohydrins. Violet coloration of the organic layer was ascribed to formation of IBr. Deiodination was followed by phenyl migration and deprotonation leading to formation of phenyl acetone and 2-phenylpropanal in good yields from 1-iodo-2-phenylpropan-2-ol and 2-iodo-1-phenylpropan-1-ol, respectively. Phenyl acetaldehyde--which was obtained in 92% GC yield from styrene iodohydrin--was also presumably formed in analogous manner. NBS and HOCl too were effective for transformation of styrene iodohydrin into phenyl acetaldehyde.

Alkali-metal-ion catalysis and inhibition in the nucleophilic displacement reaction of y-substituted phenyl diphenylphosphinates and diphenylphosphinothioates with alkali-metal ethoxides: effect of changing the electrophilic center from P=O to P=S.

PubMed

Um, Ik-Hwan; Shin, Young-Hee; Park, Jee-Eun; Kang, Ji-Sun; Buncel, Erwin

2012-01-16

A kinetic study of the nucleophilic substitution reaction of Y-substituted phenyl diphenylphosphinothioates 2 a-g with alkali-metal ethoxides (MOEt; M = Li, Na, K) in anhydrous ethanol at (25.0±0.1) °C is reported. Plots of pseudo-first-order rate constants (k(obsd)) versus [MOEt], the alkali ethoxide concentration, show distinct upward (KOEt) and downward (LiOEt) curvatures, respectively, pointing to the importance of ion-pairing phenomena and a differential reactivity of dissociated EtO(-) and ion-paired MOEt. Based on ion-pairing treatment of the kinetic data, the k(obsd) values were dissected into k EtO - and k(MOEt), the second-order rate constants for the reaction with the dissociated EtO(-) and ion-paired MOEt, respectively. The reactivity of MOEt toward 2 b (Y = 4-NO(2)) increases in the order LiOEtNaOEt>KOEt>EtO(-). The current study based on Yukawa-Tsuno analysis has revealed that the reactions of 2 a-g (P=S) and Y-substituted phenyl diphenylphosphinates 1 a-g (P=O) with MOEt proceed through the same concerted mechanism, which indicates that the contrasting selectivity patterns are not due to a difference in reaction mechanism. The P=O compounds 1 a-g are approximately 80-fold more reactive than the P=S compounds 2 a-g toward the dissociated EtO(-) (regardless of the electronic nature of substituent Y) but are up to 3.1×10(3)-fold more reactive toward ion-paired LiOEt. The origin of the contrasting selectivity patterns is further discussed on the basis of competing electrostatic effects and solvational requirements as a function of anionic electric field strength and cation size (Eisenman's theory). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Proton transfer complexes based on some π-acceptors having acidic protons with 3-amino-6-[2-(2-thienyl)vinyl]-1,2,4-triazin-5(4 H)-one donor: Synthesis and spectroscopic characterizations

NASA Astrophysics Data System (ADS)

Refat, Moamen S.; Saad, Hosam A.; Adam, Abdel Majid A.

2011-05-01

Charge transfer complexes based on 3-amino-6-[2-(2-thienyl)vinyl]-1,2,4-triazin-5(4 H)-one (ArNH 2) organic basic donor and pi-acceptors having acidic protons such as picric acid (PiA), hydroquinone (Q(OH) 2) and 3,5-dinitrobenzene (DNB) have been synthesized and spectroscopically studied. The sbnd NH3+ ammonium ion was formed under the acid-base theory through proton transfer from an acidic to basic centers in all charge transfer complexes resulted. The values of formation constant ( KCT) and molar extinction coefficient ( ɛCT) which were estimated from the spectrophotometric studies have a dramatic effect for the charge transfer complexes with differentiation of pi-acceptors. For further studies the vibrational spectroscopy of the [( ArNH3+)(PiA -)] (1), [( ArNH3+)(Q (OH)2-)] (2) and [( ArNH3+)(DNB -)] (3) of (1:1) charge transfer complexes of (donor: acceptor) were characterized by elemental analysis, infrared spectra, Raman spectra, 1H and 13CNMR spectra. The experimental data of elemental analyses of the charge transfer complexes (1), (2) and (3) were in agreement with calculated data. The IR and Raman spectra of (1), (2) and (3) are indicated to the presence of bands around 3100 and 1600 cm -1 distinguish to sbnd NH3+. The thermogravimetric analysis (TG) and differential scanning calorimetry (DSC) techniques were performed to give knowledge about thermal stability behavior of the synthesized charge transfer complexes. The morphological features of start materials and charge transfer complexes were investigated using scanning electron microscopy (SEM) and optical microscopy.

40 CFR 721.10022 - Benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs.

Code of Federal Regulations, 2010 CFR

2010-07-01

... Significant New Uses for Specific Chemical Substances § 721.10022 Benzenamine, N-phenyl-, ar′-(C9-rich C8-10... chemical substance identified as benzenamine, N-phenyl-, ar′-(C9-rich C8-10-branched alkyl) derivs (PMN P...

The identification and analytical characterization of 2,2'-difluorofentanyl.

PubMed

Liu, Cuimei; Li, Tao; Han, Yu; Hua, Zhendong; Jia, Wei; Qian, Zhenhua

2018-04-01

New psychoactive substances (NPS) have expanded their distribution and become widely available in the global market in recent years. The illicit use of fentanyl and its analogs has become an important worldwide concern linked to their high potency and risk of fatal overdose. This study describes the analytical characterization of a new fentanyl derivative N-(1-(2-fluorophenethyl)-4-piperidinyl)-N-(2-fluorophenyl)propionamide (2,2'-difluorofentanyl). Identification was based on ultra-high-performance liquid chromatography-quadrupole time-of-flight-mass spectrometry (UHPLC-QTOF-MS), gas chromatography-mass spectrometry (GC-MS), Fourier transform infrared (FTIR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy. To our knowledge, this study is the first to report on analytical data for this compound. The most abundant fragment ion in the electrospray ionization (ESI) mass spectrum under collision-induced dissociation (CID) mode was formed by the cleavage between the piperidine ring and the N-phenyl-amide moiety of the protonated molecule. Two diagnostic ions in the electron ionization (EI) mass spectrum were formed by the loss of a tropylium ion (M-91), and by the degradation of the piperidine ring and dissociate of the COC 2 H 5 moiety altogether, respectively. Copyright © 2017 John Wiley & Sons, Ltd.

Mouse pharmacokinetics and metabolism of the curcumin analog, 4-piperidinone,3,5-bis[(2-fluorophenyl)methylene]-acetate(3E,5E) (EF-24; NSC 716993).

PubMed

Reid, Joel M; Buhrow, Sarah A; Gilbert, Judith A; Jia, Lee; Shoji, Mamoru; Snyder, James P; Ames, Matthew M

2014-06-01

Curcumin, a keto-enol constituent of turmeric, has in vitro and in vivo antitumor activity. However, in vivo potency is low due to poor oral absorption. The mono-carbonyl analog, 3,5-bis[(2-fluorophenyl)methylene]-4-piperidinone acetate (EF-24, NSC 716993), exhibited broad-spectrum activity in the NCI anticancer cell line screen and potent antiangiogenesis activity in a HUVEC cell migration assay. The purpose of this study was to characterize the preclinical pharmacology of EF-24 in mice. EF-24 plasma stability, protein binding, pharmacokinetics, and metabolism were characterized utilizing an LC/MS/MS assay. An LC/MS/MS assay incorporated protein precipitation with methanol, reverse-phase HPLC separation under gradient elution using an aqueous methanol mobile phase containing 0.1 % formic acid, and positive electrospray ionization detection of the m/z 312 > 149 transition for EF-24. The assay was linear over the range 7.8-1,000 nM. Plasma protein binding was >98 % with preferential binding to albumin. EF-24 plasma disposition in mice after i.v. administration of a 10 mg/kg dose was best fit to a 3-compartment open model. The terminal elimination half-life and plasma clearance values were 73.6 min and 0.482 L/min/kg, respectively. EF-24 bioavailability was 60 and 35 % after oral and i.p. administration, respectively. NADPH-dependent metabolism of EF-24 loss in liver microsomal preparations yielded several metabolites consistent with EF-24 hydroxylation and reduction.

3-Phenyl-6-(2-pyrid-yl)-1,2,4,5-tetra-zine.

PubMed

Chartrand, Daniel; Laverdière, François; Hanan, Garry

2007-12-06

The title compound, C(13)H(9)N(5), is the first asymmetric diaryl-1,2,4,5-tetra-zine to be crystallographically characterized. We have been inter-ested in this motif for incorporation into supra-molecular assemblies based on coordination chemistry. The solid state structure shows a centrosymmetric mol-ecule, forcing a positional disorder of the terminal phenyl and pyridyl rings. The mol-ecule is completely planar, unusual for aromatic rings with N atoms in adjacent ortho positions. The stacking observed is very common in diaryl-tetra-zines and is dominated by π stacking [centroid-to-centroid distance between the tetrazine ring and the aromatic ring of an adjacent molecule is 3.6 Å, perpendicular (centroid-to-plane) distance of about 3.3 Å].

Exploring selectivity requirements for COX-2 versus COX-1 binding of 2-(5-phenyl-pyrazol-1-yl)-5-methanesulfonylpyridines using topological and physico-chemical parameters.

PubMed

Chakraborty, Santanu; Sengupta, Chandana; Roy, Kunal

2005-04-01

Considering the current need for development of selective cyclooxygenase-2 (COX-2) inhibitors, an attempt has been made to explore physico-chemical requirements of 2-(5-phenyl-pyrazol-1-yl)-5-methanesulfonylpyridines for binding with COX-1 and COX-2 enzyme subtypes and also to explore the selectivity requirements. In this study, E-states of different common atoms of the molecules (calculated according to Kier & Hall), first order valence connectivity and physicochemical parameters (hydrophobicity pi, Hammett sigma and molar refractivity MR of different ring substituents) were used as independent variables along with suitable dummy parameters in the stepwise regression method. The best equation describing COX-1 binding affinity [n = 25, Q2 = 0.606, R(a)2 = 0.702, R2 = 0.752, R = 0.867, s = 0.447, F = 15.2 (df 4, 20)] suggests that the COX-1 binding affinity increases in the presence of a halogen substituent at R1 position and a p-alkoxy or p-methylthio substituent at R2 position. Furthermore, a difluoromethyl group is preferred over a trifluoromethyl group at R position for the COX-1 binding. The best equation describing COX-2 binding affinity [n = 32, Q2 = 0.622, R(a)2= 0.692, R2 = 0.732, R = 0.856, s = 0.265, F = 18.4 (df 4, 27)] shows that the COX-2 binding affinity increases with the presence of a halogen substituent at R1 position and increase of size of R2 substituents. However, it decreases in case of simultaneous presence of 3-chloro and 4-methoxy groups on the phenyl nucleus and in the presence of highly lipophilic R2 substituents. The best selectivity relation [n = 25, Q2 = 0.455, R(a)2 = 0.605, R2 = 0.670, R = 0.819, s = 0.423, F = 10.2 (df 4, 20)] suggests that the COX-2 selectivity decreases in the presence of p-alkoxy group and electron-withdrawing para substituents at R2 position. Again, a trifluoro group is conductive for the selectivity instead of a difluoromethyl group at R position. Furthermore, branching may also play significant role in

40 CFR 721.4098 - Substituted heteroaromatic-2[[4-(dimethylamino) phenyl]azo]-3-methyl-, salts (generic).

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Substituted heteroaromatic-2[[4-(dimethylamino) phenyl]azo]-3-methyl-, salts (generic). 721.4098 Section 721.4098 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for...

40 CFR 721.267 - N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name).

Code of Federal Regulations, 2010 CFR

2010-07-01

... ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.267 N-[2-[(substituted dinitrophenyl)azo]diallylamino-4- substituted phenyl] acetamide (generic name). (a) Chemical substance and...

pi-Selective stationary phases: (II) Adsorption behavior of substituted aromatic compounds on n-alkyl-phenyl stationary phases

DOE Office of Scientific and Technical Information (OSTI.GOV)

Gritti, Fabrice; Guiochon, Georges A; Mayfield, Kirsty

2010-01-01

The frontal analysis method was used to measure the adsorption isotherms of phenol, 4-chlorophenol, p-cresol, 4-methoxyphenol and caffeine on a series of columns packed with home-made alkyl-phenyl bonded silica particles. These ligands consist of a phenyl ring tethered to the silica support via a carbon chain of length ranging from 0 to 4 atoms. The adsorption isotherm models that fit best to the data account for solute-solute interactions that are likely caused by p-p interactions occurring between aromatic compounds and the phenyl group of the ligand. These interactions are the dominant factor responsible for the separation of low molecular weightmore » aromatic compounds on these phenyl-type stationary phases. The saturation capacities depend on whether the spacer of the ligands have an even or an odd number of carbon atoms, with the even alkyl chain lengths having a greater saturation capacity than the odd alkyl chain lengths. The trends in the adsorption equilibrium constant are also significantly different for the even and the odd chain length ligands.« less

A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors.

PubMed

Salian, Vinutha V; Narayana, Badiadka; Yathirajan, Hemmige S; Akkurt, Mehmet; Çelik, Ömer; Ersanlı, Cem Cüneyt; Glidewell, Christopher

2015-07-01

Four compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)-1-(2,4-Dichlorophenyl)-3- [4-(prop-1-en-2-yl)phenyl]prop-2-en-1-one, C18H14Cl2O, (I), prepared from 4-(prop-1-en-2-yl)benzaldehyde and 2,4-dichloroacetophenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)-3-(4-chlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one reacts with acetone to produce (5RS)-3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]cyclohex-2-en-1-one, C21H21ClO, (II), which exhibits enantiomeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3-oxobutanoate to give methyl (1RS,6SR)-4-(4-chlorophenyl)-6-[4-(propan-2-yl)phenyl]-2-oxocyclohex-3-ene-1-carboxylate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, of ethyl (1RS,6SR)-6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate, prepared in a similar manner to (II) and (III), produces ethyl 4''-bromo-4-fluoro-5'-hydroxy-1,1':3',1''-terphenyl-4'-carboxylate, C21H16BrFO3, (IV), which crystallizes with Z' = 2 in the space group P-1. There are no significant intermolecular interactions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the molecules are linked into sheets by a combination of C-H...O and C-H...π(arene) hydrogen bonds. The two independent molecules of compound (IV) form two different centrosymmetric dimers, one built from inversion-related pairs of C-H...O hydrogen bonds and the other from inversion-related pairs of C-H...π(arene) hydrogen bonds. Comparisons are made with related compounds.

Conformational studies of lithium phenyl stearate

NASA Astrophysics Data System (ADS)

Barron, Christopher

The structure and conformation of lithium phenyl stearate (and to a lesser extent, for comparative purposes, cadmium stearate) was investigated using Fourier transform infrared spectroscopy, and various modelling techniques. The infrared results for LiPS show that the aliphatic portion of the soap molecule is much more ordered at room temperature than had been expected, having only 0.62 and 0.60 gtg and gg defects per molecule respectively, where an isotropic chain would have 1.35 and 1.21 gtg and gg defects per chain respectively. As the temperature is increased the number of conformational defects increases continuously, until at <130°C the chain reaches an isotropic degree of disorder. At this point the phase transition begins, so the chain reaches liquid like disorder before the phase transition begins.Modelling of the phenyl stearic acid showed that the phenyl group was restricted to certain angle of rotation values, and that the bonds close to the phenyl group were prevented from attaining true rotational isomeric state conformations, gtg defects near the phenyl group were distorted only slightly from their usual angular position, and an additional band in the infrared spectrum of LiPS at 1363 cm-1 has been assigned to this distorted gtg/gtg' defect. The gg defects near the phenyl group have a much greater distortion (and energy) resulting in a much reduced probability of occurrence. The number of gg defects present at the phase transition (<130°C) was only 75% of that expected for an isotropic n-alkane of equivalent chain length, indicating that the four bonds nearest to the phenyl group have a reduced probability of forming a gg defect.The modelling of the ionic core of LiPS gives a reasonable estimate of between 5.6 to 7.1 A for the core radius. When this is used to calculate the hexagonal cylinder diameter, at room temperature, along with the average chain extension, it gives a value for the cylinder diameter of between 33.9 to 36.8A. The hexagonal

The crystal structures of two isomers of 5-(phenyl-iso-thia-zol-yl)-1,3,4-oxa-thia-zol-2-one.

PubMed

Zhu, Shuguang; Schriver, Melbourne J; Hendsbee, Arthur D; Masuda, Jason D

2017-11-01

The syntheses and crystal structures of two isomers of phenyl iso-thia-zolyl oxa-thia-zolone, C 11 H 6 N 2 O 2 S 2 , are described [systematic names: 5-(3-phenyl-iso-thia-zol-5-yl)-1,3,4-oxa-thia-zol-2-one, (I), and 5-(3-phenyl-iso-thia-zol-4-yl)-1,3,4-oxa-thia-zol-2-one, (II)]. There are two almost planar (r.m.s. deviations = 0.032 and 0.063 Å) mol-ecules of isomer (I) in the asymmetric unit, which form centrosymmetric tetra-mers linked by strong S⋯N [3.072 (2) Å] and S⋯O contacts [3.089 (1) Å]. The tetra-mers are π-stacked parallel to the a -axis direction. The single mol-ecule in the asymmetric unit of isomer (II) is twisted into a non-planar conformation by steric repulsion [dihedral angles between the central iso-thia-zolyl ring and the pendant oxa-thia-zolone and phenyl rings are 13.27 (6) and 61.18 (7)°, respectively], which disrupts the π-conjugation between the heteroaromatic iso-thia-zoloyl ring and the non-aromatic oxa-thia-zolone heterocycle. In the crystal of isomer (II), the strong S⋯O [3.020 (1) Å] and S⋯C contacts [3.299 (2) Å] and the non-planar structure of the mol-ecule lead to a form of π-stacking not observed in isomer (I) or other oxa-thia-zolone derivatives.

Simultaneous cross-linking and p-doping of a polymeric semiconductor film by immersion into a phosphomolybdic acid solution for use in organic solar cells.

PubMed

Aizawa, Naoya; Fuentes-Hernandez, Canek; Kolesov, Vladimir A; Khan, Talha M; Kido, Junji; Kippelen, Bernard

2016-03-07

Poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT) is shown to be simultaneously cross-linked and p-doped when immersed into a phosphomolybdic acid solution, yielding conductive films with low solubility that can withstand the solution processing of subsequent photoactive layers. Such a modified PCDTBT film serves to improve hole collection and limit carrier recombination in organic solar cells.

Synthesis, spectral and antimicrobial activity of Zn(II) complexes with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde/2-hydroxyacetophenone/indoline-2,3-dione

NASA Astrophysics Data System (ADS)

Singh, Ajay K.; Pandey, O. P.; Sengupta, S. K.

2013-09-01

Zn(II) complexes have been synthesized by reacting zinc acetate with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and 2-hydroxyacetophenone/benzaldehyde/indoline-2,3-dione. All these complexes are soluble in DMF and DMSO; low molar conductance values indicate that they are non electrolytes. Elemental analyses suggest that the complexes have 1:2 metal to ligands stoichiometry of the types [ZnL2(H2O)2](L = monoanionic Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and 2-hydroxyacetophenone/indoline-2,3-dione) [ZnL2‧(OOCCH3)2(H2O)2](L‧ = neutral Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde), and they were characterized by IR, 1H NMR, and 13C NMR. Particle sizes of synthesized compounds were measured with dynamic light scattering (DLS) analyser which indicates that particle diameter are of the range ca. 100-200 nm. All these Schiff bases and their complexes have also been screened for their antibacterial (Bacillus subtilis (B. subtilis), Escherichia coli (E. coli) and antifungal activities (Colletotrichum falcatum (C. falcatum), Aspergillus niger (A. niger), Fusarium oxysporium (F. oxysporium) Curvularia pallescence (C. pallescence). The antimicrobial activities have shown that upon complexation the activity increases.

Structural, optical and device characteristics of 1-(2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H-pyrazol-4-yl)-2-oxoethyl)pyridinium chloride

NASA Astrophysics Data System (ADS)

El-Menyawy, E. M.; Elagamey, A. A.; Elgogary, S. R.; Shalof, R. T.

2016-03-01

1-(2-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H-pyrazol-4-yl)-2-oxoethyl)pyridinium chloride (DOPC) was chemically synthesized and showed thermal stability up to 220 °C. DOPC powder has polycrystalline structure and crystallizes in triclinic structure with space group, Pbar{1} . Miller indices for each diffraction plan in X-ray diffraction spectra are determined. DOPC films have been prepared via spin-coating technique onto quartz and silicon single crystal substrates. The optical properties of the films are investigated by spectrophotometric measurements of the transmittance and reflectance over the spectral range 200-2500 nm. The absorption coefficient and the refractive index of the films are calculated in which the optical band gap and single oscillator parameters are estimated. Hybrid Au/DOPC/p-Si/Al heterojunction is constructed, and the dark current-voltage characteristics are recorded. The device exhibited rectification behavior and the basic parameters such as ideality factor, barrier height, series resistance and charge carrier mobility are evaluated.

Synthesis, characterization, crystal structure and theoretical studies of 4-[(E)-(3-chloro-4-hydroxyphenyl) diazenyl]-1, 5-dimethyl-2-phenyl-1, 2-dihydro-3H-pyrazol-3-one

NASA Astrophysics Data System (ADS)

Athira, L. S.; Lakshmi, C. S. Nair; Balachandran, S.; Arul Dhas, D.; Hubert Joe, I.

2017-11-01

Crystals of new heterocyclic azo compound of 4-aminoantipyrine, 4-[(E)-(3-chloro-4-hydroxyphenyl)diazenyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one have been grown by slow evaporation method at room temperature and its structural characterization was performed by X- ray diffraction method. The spectroscopic characterization was also performed by FT-IR, UV-Vis, 13C and 1H NMR techniques. The compound crystallizes in the monoclinic CC space group with cell dimensions a = 12.4842 (13), b = 16.4492 (16), c = 8.3389 (8) and β = 102.698 (3)°. The phenyl ring attached to the pyrazolone moiety is disordered over two positions with an occupancy ratio 52:48. The components of the disorder were refined. DFT calculations have been performed by using B3LYP/6-311G (d,p) level basis set. The calculated vibrational frequency showed a red shift for Cdbnd O and OH stretching. The natural bond orbital analysis of monomer, dimer and trimer structures reveals the absence of intramolecular hydrogen bonding; however intermolecular hydrogen bonding is observed. The cationic and anionic reactive sites of compound have been visualized on MEP surface.

Highly optical transparency and thermally stable polyimides containing pyridine and phenyl pendant.

PubMed

Yao, Jianan; Wang, Chunbo; Tian, Chengshuo; Zhao, Xiaogang; Zhou, Hongwei; Wang, Daming; Chen, Chunhai

2017-01-01

In order to obtain highly optical transparency polyimides, two novel aromatic diamine monomers containing pyridine and kinky structures, 1,1-bis[4-(5-amino-2-pyridinoxy)phenyl]diphenylmethane (BAPDBP) and 1,1-bis[4-(5-amino-2-pyridinoxy)phenyl]-1-phenylethane (BAPDAP), were designed and synthesized. Polyimides based on BAPDBP, BAPDAP, 2,2-bis[4-(5-amino-2-pyridinoxy)phenyl]propane (BAPDP) with various commercial dianhydrides were prepared for comparison and structure-property relationships study. The structures of the polyimides were characterized by Fourier transform infrared (FT-IR) spectrometer, wide-angle X-ray diffractograms (XRD) and elemental analysis. Film properties including solubility, optical transparency, water uptake, thermal and mechanical properties were also evaluated. The introduction of pyridine and kinky structure into the backbones that polyimides presented good optical properties with 91-97% transparent at 500 nm and a low cut-off wavelength at 353-398 nm. Moreover, phenyl pendant groups of the polyimides showed high glass transition temperatures ( T g ) in the range of 257-281 °C. These results suggest that the incorporating pyridine, kinky and bulky substituents to polymer backbone can improve the optical transparency effectively without sacrificing the thermal properties.

The crystal structure of a new ferrocenyl P,N ligand: 1-[(2,2-di-methyl-hydrazin-1-yl-idene)meth-yl]-1'-(di-phenyl-phospho-rothio-yl)ferrocene.

PubMed

Mouas, Toma Nardjes; Daran, Jean-Claude; Merazig, Hocine; Manoury, Eric

2018-02-01

The asymmetric unit of the title compound, [Fe(C 8 H 11 N 2 )(C 17 H 14 PS)], contains two independent mol-ecules ( A and B ) with very similar conformations. Each mol-ecule is built up from a ferrocene unit substituted in the 1 and 1' positions by a protected sulfur di-phenyl-phosphine and by a di-methyl-hydrazine, -C(H)=N-N(CH 3 ) 2 , fragment. The two independent mol-ecules are linked by a C-H⋯N hydrogen bond. In the crystal, the A - B dimer is linked by a pair of C-H⋯S hydrogen bonds, forming a centrosymmetric four-mol-ecule arrangement. These units are linked by C-H⋯π inter-actions, forming a supra-molecular three-dimensional structure.

Synthesis, crystal growth, single crystal X-ray analysis and vibrational spectral studies of (2E)-3-(2-chloro-4-fluorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one: A combined DFT study

NASA Astrophysics Data System (ADS)

Chidan Kumar, C. S.; Balachandran, V.; Fun, Hoong-Kun; Chandraju, Siddegowda; Quah, Ching Kheng

2015-11-01

A new chalcone derivative, (2E)-3-(2-chloro-4-fluorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (a) was synthesized and single crystals were grown by slow evaporation technique. The FT-Raman and FT-IR spectra of the sample were recorded in the region 3500-100 cm-1 and 4000-400 cm-1 respectively. The spectra were interpreted with the aid of normal coordinate analysis, following structure optimizations and force field calculations based on B3LYP/6-31G (d) level of theory. Normal coordinate calculations were performed using the DFT force field corrected by a recommended set of scaling factors yielding fairly good agreement between the observed and calculated wavenumbers. The total electron density and molecular electrostatic potential surfaces of the molecule were constructed using B3LYP/6-31G (d) method to display electrostatic potential (electron + nuclei) distribution, molecular shape, size, and dipole moments of the molecule. HOMO and LUMO energies were also calculated. Stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital (NBO) analysis. Global and local reactivity descriptors and dipole moment (μ), static polarizability (α), first order hyperpolarizability (β) and optical gap (ΔE) were also calculated to study the NLO property of our title compound.

Enantioconvergent production of (R)-1-phenyl-1,2-ethanediol from styrene oxide by combining the Solanum tuberosum and an evolved Agrobacterium radiobacter AD1 epoxide hydrolases.

PubMed

Cao, Li; Lee, Jintae; Chen, Wilfred; Wood, Thomas K

2006-06-20

Soluble epoxide hydrolase (EH) from the potato Solanum tuberosum and an evolved EH of the bacterium Agrobacterium radiobacter AD1, EchA-I219F, were purified for the enantioconvergent hydrolysis of racemic styrene oxide into the single product (R)-1-phenyl-1,2-ethanediol, which is an important intermediate for pharmaceuticals. EchA-I219F has enhanced enantioselectivity (enantiomeric ratio of 91 based on products) for converting (R)-styrene oxide to (R)-1-phenyl-1,2-ethanediol (2.0 +/- 0.2 micromol/min/mg), and the potato EH converts (S)-styrene oxide primarily to the same enantiomer, (R)-1-phenyl-1,2-ethanediol (22 +/- 1 micromol/min/mg), with an enantiomeric ratio of 40 +/- 17 (based on substrates). By mixing these two purified enzymes, inexpensive racemic styrene oxide (5 mM) was converted at 100% yield to 98% enantiomeric excess (R)-1-phenyl-1,2-ethanediol at 4.7 +/- 0.7 micromol/min/mg. Hence, at least 99% of substrate is converted into a single stereospecific product at a rapid rate. 2006 Wiley Periodicals, Inc.

Supercritical Fluid Chromatography with Photodiode Array Detection in the Determination of Fat-Soluble Vitamins in Hemp Seed Oil and Waste Fish Oil.

PubMed

Tyśkiewicz, Katarzyna; Gieysztor, Roman; Maziarczyk, Izabela; Hodurek, Paweł; Rój, Edward; Skalicka-Woźniak, Krystyna

2018-05-10

In the presented study for the first time a new, optimized, fast SFC (supercritical fluid chromatography) method was applied to separate in one run fat-soluble vitamins from waste fish oil, including cis -and tran s-retinyl palmitate, cis - and trans -retinyl acetate, retinol, α-tocopherol, β-tocopherol, γ‑tocopherol, δ-tocopherol, ergocalciferol (D₂), cholecalciferol (D₃), cis - and trans -phylloquinone (K₁) and menaquinone-4 (K₂-MK4). Vitamins were baseline separated on an Acquity UPC² (ultra performance convergence chromatography) HSS C18 SB (highly strength chemically modified silica) column within 13 min. The influence of the stationary phase, such as Torus 1-AA (1-aminoanthracene), Torus Diol (high density diol), Torus DEA (diethylamine), BEH (silica with no bonding), BEH-2EP (2-ethylpirydine), CSH Fluoro-Phenyl (silica with fluoro-phenyl groups), column temperature, flow rate and back pressure on the separation of the compounds was described. The application of the modified saponification procedure allowed us to increase concentration in the sample prepared for the analysis of γ‑tocopherol from less than 1% (wt %) to 14% for the first time. In addition, α‑tocopherol, γ‑tocopherol, δ‑tocopherol and retinol were identified in waste fish oil. Vitamin purification and analysis in waste fish oil are reported for the first time here. Due to the short time and effectiveness of the proposed method, it can be easily applied in industrial processes.

2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions.

PubMed

Huang, Zhongyan; Okuyama, Kenta; Wang, Chen; Tokunaga, Etsuko; Li, Xiaorui; Shibata, Norio

2016-06-01

2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one (diazo-triflone) ( 2 ) is not only a building block but also a reagent. In this study, diazo-triflone, which was originally used for the synthesis of β-lactam triflones as a trifluoromethanesulfonyl (SO 2 CF 3 ) building block under catalyst-free thermal conditions, is redisclosed as an effective electrophilic trifluoromethylthiolation reagent under copper catalysis. A broad set of enamines, indoles, β-keto esters, pyrroles, and anilines were nicely transformed into corresponding trifluoromethylthio (SCF 3 ) compounds in good to high yields by diazo-triflone under copper catalysis via an electrophilic-type reaction. A coupling-type trifluoromethylthiolation reaction of aryl iodides was also realized by diazo-triflone in acceptable yields.

NSAI activity study of 4-phenyl-2-thioxo-benzo[4,5]thieno[2,3-d]pyrimidine derivatives.

PubMed

Darias, V; Abdallah, S S; Tello, M L; Delgado, L D; Vega, S

1994-12-01

A series of 4-phenyl-2-thioxo-benzo[4,5]thieno[2,3-d]pyrimidine derivatives endowed with anti-inflammatory and related pharmacological properties were submitted to a more extensive study to know their exact pharmacological profile and their possible side effects. The studied compounds possess a remarkable analgesic activity, devoid of central effects. They also show an interesting anti-inflammatory profile evidenced by their effectiveness in different experimental models of inflammation. In addition, these compounds exhibit none or very little activity on CNS, scarce toxicity and low gastrointestinal aggressivity.

Mouse pharmacokinetics and metabolism of the curcumin analog, 4-Piperidione,3,5-bis[(2-fluorophenyl)methylene]-acetate(3E,5E) (EF-24; NSC 716993)

PubMed Central

Reid, Joel M.; Buhrow, Sarah A.; Gilbert, Judith A.; Jia, Lee; Shoji, Mamoru; Snyder, James P.; Ames, Matthew M.

2015-01-01

Purpose Curcumin, a keto-enol constituent of turmeric, has in vitro and in vivo antitumor activity. However, in vivo potency is low due to poor oral absorption. The mono-carbonyl analog, 3,5-bis[(2-fluorophenyl)methylene]-4-piperidinone acetate (EF-24, NSC 716993), exhibited broad spectrum activity in the NCI anti-cancer cell line screen and potent anti-angiogenesis activity in a HUVEC cell migration assay. The purpose of this study was to characterize the preclinical pharmacology of EF-24 in mice. Methods EF-24 plasma stability, protein binding, pharmacokinetics and metabolism were characterized utilizing an LC/MS/MS assay. Results An LC/MS/MS assay that incorporated protein precipitation with methanol, reverse-phase HPLC separation under gradient elution using an aqueous methanol mobile phase containing 0.1% formic acid and positive electrospray ionization detection of the m/z 312 > 149 transition for EF-24. The assay was linear over the range 7.8-1000 nM. Plasma protein binding was > 98% with preferential binding to albumin. EF-24 plasma disposition in mice after i.v. administration of a 10 mg/kg dose was best fit to a 3-compartment open model. The terminal elimination half-life and plasma clearance values were 73.6 min and 0.482 L/min/kg, respectively. EF-24 bioavailability was 60% and 35% after oral and i.p. administration, respectively. NADPH-dependent metabolism of EF-24 loss in liver microsomal preparations yielded several metabolites consistent with EF-24 hydroxylation and reduction. PMID:24760417

Microwave Assisted Enzymatic Kinetic Resolution of (±)-1-Phenyl-2-propyn-1-ol in Nonaqueous Media

PubMed Central

Devendran, Saravanan; Yadav, Ganapati D.

2014-01-01

Kinetic resolution of 1-phenyl-2-propyn-1-ol, an important chiral synthon, was studied through trans-esterification with acyl acetate to investigate synergism between microwave irradiation and enzyme catalysis. Lipases from different microbial origins were employed for the kinetic resolution of (R/S)-1-phenyl-2-propyn-1-ol, among which Candida antarctica lipase B, immobilized on acrylic resin (Novozym 435), was found to be the best catalyst in n-hexane as solvent. Vinyl acetate was the most effective among different acyl esters studied. The effect of various parameters was studied in a systematic manner. Definite synergism between microwave and enzyme was observed. The initial rate was improved around 1.28 times under microwave irradiation than conventional heating. Under optimum conditions, maximum conversion (48.78%) and high enantiomeric excess (93.25%) were obtained in 2 h. From modeling studies, it is concluded that the reaction follows the Ping-Pong bi-bi mechanism with dead end alcohol inhibition. Kinetic parameters were obtained by using nonlinear regression. This process is green, clean, and easily scalable as compared to the chemical process. PMID:24707487

Crystal structure of {2,6-bis-[(di-methyl-amino)-meth-yl]phenyl-κ3N,C1,N'}(bromido/chlorido)-mercury(II).

PubMed

Gupta, Anand; Singh, Harkesh B; Butcher, Ray J

2017-11-01

In the mol-ecular structure of the title compound, {2,6-bis-[(di-methyl-amino)-meth-yl]phenyl-κ 3 N , C 1 , N '}[bromido/chlorido-(0.30/0.70)]mercury(II)-{2,6-bis-[(di-methyl-amino)-meth-yl]phenyl-κ 3 N , C 1 , N '}[bromido/chlorido-(0.24/0.76)]mer-cury(II) (1/1), [HgBr 0.30 Cl 0.70 (C 12 H 19 N 2 )]·[HgBr 0.24 Cl 0.76 (C 12 H 19 N 2 )], there are two mol-ecules in the asymmetric unit of formula L Hg X { L = 2,6-bis-[(di-methyl-amino)-meth-yl]phenyl and X = Cl/Br}. In each mol-ecule, the halide site is mixed Cl/Br, with occupancies of 0.699 (7):0.301 (7) and 0.763 (7):0.237 (7), respectively. The two mol-ecules are linked into dimers by a combination of Hg⋯Hg [Hg⋯Hg = 3.6153 (3) Å] and C-H⋯Cl and C-H⋯π inter-actions.

Synthesis and Evaluation of 15-(4-(2-[18F]Fluoroethoxy)phenyl)pentadecanoic Acid: a Potential PET Tracer for Studying Myocardial Fatty Acid Metabolism

PubMed Central

Tu, Zhude; Li, Shihong; Sharp, Terry L.; Herrero, Pilar; Dence, Carmen S.; Gropler, Robert J.; Mach, Robert H.

2010-01-01

15-(4-(2-[18F]fluoroethoxy)phenyl)pentadecanoic acid ([18F]7) was synthesized as a PET probe for assessing myocardial fatty acid metabolism. The radiosynthesis of [18F]7 was accomplished using a two step reaction, starting with the corresponding tosylate ester, methyl 15-(4-(2-(tosyloxy)ethoxy)phenyl)pentadecanoate (5) and gave the radiolabeled fatty acid, [18F]7 in a radiolabeling yield of 55 – 60% and a specific activity of > 2,000 Ci/mmol (decay corrected to EOB). The biological evaluation of [18F]7 in rats displayed high uptake in heart (1.94%.ID/g at 5 min), which was higher than the uptake (%ID/g) in blood, lung, muscle, pancreas and brain. MicroPET studies of [18F]7 in Sprague-Dawley rats demonstrated excellent images of the myocardium when compared with [11C]palmitate images in the same animal. Moreover, the tracer kinetics of [18F]7 paralleled those seen with [11C]palmitate, with an early peak followed by biphasic washout. When compared to [11C]palmitate, [18F]7 exhibited a slower early clearance (0.17 ± 0.01 vs. 0.30 ± 0.02, P < 0.0001) and a significantly higher late clearance (0.0030 ± 0.0005 vs. 0.0006 ± 0.00013, P < 0.01). These initial studies suggest that [18F]7 could be a potentially useful clinical PET tracer to assess abnormal myocardial fatty acid metabolism. PMID:21070001

Comprehensive quantum chemical and spectroscopic (FTIR, FT-Raman, (1)H, (13)C NMR) investigations of (1,2-epoxyethyl)benzene and (1,2-epoxy-2-phenyl)propane.

PubMed

Arjunan, V; Anitha, R; Devi, L; Mohan, S; Yang, Haifeng

2015-01-25

Aromatic epoxides are causative factors for mutagenic and carcinogenic activity of polycyclic arenes. The 1,2- or 2,3-epoxy compounds are widely used to a considerable extent in the textile, plastics, pharmaceutical, cosmetics, detergent and photochemical industries. The FTIR and FT-Raman spectra of (1,2-epoxyethyl)benzene and (1,2-epoxy-2-phenyl)propane are recorded in the regions 4000-400 cm(-1) and 4000-100 cm(-1), respectively. The observed fundamentals are assigned to different normal modes of vibration. The structure of the compound has been optimised with B3LYP method using 6-311++G(**) and cc-pVTZ basis sets. The IR and Raman intensities are determined. The total electron density and molecular electrostatic potential surfaces of the molecule are constructed by using B3LYP/6-311++G(d,p) method to display electrostatic potential (electron+nuclei) distribution. The electronic properties HOMO and LUMO energies were measured. Natural bond orbital analysis of the compounds has been performed to indicate the presence of intramolecular charge transfer. The (1)H and (13)C NMR chemical shifts of the molecules have been analysed. Copyright © 2014 Elsevier B.V. All rights reserved.

Comprehensive quantum chemical and spectroscopic (FTIR, FT-Raman, 1H, 13C NMR) investigations of (1,2-epoxyethyl)benzene and (1,2-epoxy-2-phenyl)propane

NASA Astrophysics Data System (ADS)

Arjunan, V.; Anitha, R.; Devi, L.; Mohan, S.; Yang, Haifeng

2015-01-01

Aromatic epoxides are causative factors for mutagenic and carcinogenic activity of polycyclic arenes. The 1,2- or 2,3-epoxy compounds are widely used to a considerable extent in the textile, plastics, pharmaceutical, cosmetics, detergent and photochemical industries. The FTIR and FT-Raman spectra of (1,2-epoxyethyl)benzene and (1,2-epoxy-2-phenyl)propane are recorded in the regions 4000-400 cm-1 and 4000-100 cm-1, respectively. The observed fundamentals are assigned to different normal modes of vibration. The structure of the compound has been optimised with B3LYP method using 6-311++G** and cc-pVTZ basis sets. The IR and Raman intensities are determined. The total electron density and molecular electrostatic potential surfaces of the molecule are constructed by using B3LYP/6-311++G(d,p) method to display electrostatic potential (electron + nuclei) distribution. The electronic properties HOMO and LUMO energies were measured. Natural bond orbital analysis of the compounds has been performed to indicate the presence of intramolecular charge transfer. The 1H and 13C NMR chemical shifts of the molecules have been analysed.

2,4,8,10,13-Penta­methyl-6-phenyl-13,14-dihydro-12H-6λ5-dibenzo[d,i][1,3,7,2]dioxaza­phosphecin-6-thione

PubMed Central

Krishnaiah, M.; Babu, V.H.H. Surendra; Sankar, A. Uma Ravi; Raju, C. Naga; Kant, Rajni

2010-01-01

In the title compound, C25H28NO2PS, the cyclo­decene ring exhibits a crown conformation. The two dimethyl­benzene rings which are fused symmetrically on either side of the ten-membered ring, make dihedral angles of 20.2 (1) and 18.0 (1)°. The phenyl ring substituted at P is perpendicular to the heterocyclic ring, making a dihedral angle of 88.4 (1)°. The crystal structure is stabilized by very weak intra­molecular C—H⋯O hydrogen bonding. PMID:21580010

Extreme red shifted SERS nanotags† †Electronic supplementary information (ESI) available: General experimental details for the synthesis and characterization of dyes 1–14, intermediates 15–17, and HGNs; general description of the chemometrics used for principal component analysis; figures of SERS spectra of dye/HGN nanotags with 1280 nm excitation; extinction spectrum for HGNs; SERS spectra of Au and Ag nanoparticles and dye 13 aggregated with KCl; SERS spectra of dyes 13 and 14 on HGN not aggregated with KCl; details of mean plane angle calculations, tables of crystallographic data, atomic coordinates and equivalent isotropic displacement parameters, anisotropic placement parameters, bond lengths, bond angles, and hydrogen atom coordinates and isotropic displacement parameters for dye 14. CCDC 1040064. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc03917c Click here for additional data file. Click here for additional data file.

PubMed Central

Bedics, Matthew A.; Kearns, Hayleigh; Cox, Jordan M.; Mabbott, Sam; Ali, Fatima; Shand, Neil C.; Faulds, Karen; Benedict, Jason B.

2015-01-01

Surfaced enhanced Raman scattering (SERS) nanotags operating with 1280 nm excitation were constructed from reporter molecules selected from a library of 14 chalcogenopyrylium dyes containing phenyl, 2-thienyl, and 2-selenophenyl substituents and a surface of hollow gold nanoshells (HGNs). These 1280 SERS nanotags are unique as they have multiple chalcogen atoms available which allow them to adsorb strongly onto the gold surface of the HGN thus producing exceptional SERS signals at this long excitation wavelength. Picomolar limits of detection (LOD) were observed and individual reporters of the library were identified by principal component analysis and classified according to their unique structure and SERS spectra. PMID:29308144

40 CFR 721.10075 - Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic).

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic). 721.10075 Section 721.10075 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for...

40 CFR 721.10075 - Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic).

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic). 721.10075 Section 721.10075 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for...

40 CFR 721.10075 - Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic).

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Carbon black, 4-[[2-(Sulfooxy) ethyl]substituted] phenyl- modified, sodium salts (generic). 721.10075 Section 721.10075 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for...

Synthesis, spectral and antimicrobial activity of Zn(II) complexes with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde/2-hydroxyacetophenone/indoline-2,3-dione.

PubMed

Singh, Ajay K; Pandey, O P; Sengupta, S K

2013-09-01

Zn(II) complexes have been synthesized by reacting zinc acetate with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and 2-hydroxyacetophenone/benzaldehyde/indoline-2,3-dione. All these complexes are soluble in DMF and DMSO; low molar conductance values indicate that they are non electrolytes. Elemental analyses suggest that the complexes have 1:2 metal to ligands stoichiometry of the types [ZnL2(H2O)2](L=monoanionic Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and 2-hydroxyacetophenone/indoline-2,3-dione) [ZnL2(')(OOCCH3)2(H2O)2](L'=neutral Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde), and they were characterized by IR, (1)H NMR, and (13)C NMR. Particle sizes of synthesized compounds were measured with dynamic light scattering (DLS) analyser which indicates that particle diameter are of the range ca. 100-200nm. All these Schiff bases and their complexes have also been screened for their antibacterial (Bacillus subtilis (B. subtilis), Escherichia coli (E. coli) and antifungal activities (Colletotrichum falcatum (C. falcatum), Aspergillus niger (A. niger), Fusarium oxysporium (F. oxysporium) Curvularia pallescence (C. pallescence). The antimicrobial activities have shown that upon complexation the activity increases. Copyright © 2013 Elsevier B.V. All rights reserved.

7-Meth­oxy-2-phenyl­chroman-4-one

PubMed Central

Piaskowska, Agata; Hodorowicz, Maciej; Nitek, Wojciech

2013-01-01

In the title compound, C16H14O3, the ring O atom and the two adjacent non-fused C atoms, as well as the attached phenyl ring, exhibit static disorder [occupancy ratio 0.559 (12):0.441 (12)]. The crystal packing features π–π [centroid–centroid distance = 3.912 (1) Å] and C—H⋯π inter­actions. PMID:23424545

Dissociation of protonated N-(3-phenyl-2H-chromen-2-ylidene)-benzenesulfonamide in the gas phase: cyclization via sulfonyl cation transfer.

PubMed

Wang, Shanshan; Dong, Cheng; Yu, Lian; Guo, Cheng; Jiang, Kezhi

2016-01-15

In the tandem mass spectrometry of protonated N-(3-phenyl-2H-chromen-2-ylidene)benzenesulfonamides, the precursor ions have been observed to undergo gas-phase dissociation via two competing channels: (a) the predominant channel involves migration of the sulfonyl cation to the phenyl C atom and the subsequent loss of benzenesulfinic acid along with cyclization reaction, and (b) the minor one involves dissociation of the precursor ion to give an ion/neutral complex of [sulfonyl cation/imine], followed by decomposition to afford sulfonyl cation or the INC-mediated electron transfer to give an imine radical cation. The proposed reaction channels have been supported by theoretical calculations and D-labeling experiments. The gas-phase cyclization reaction originating from the N- to C-sulfonyl cation transfer has been first reported to the best of our knowledge. For the substituted sulfonamides, the presence of electron-donating groups (R(2) -) at the C-ring effectively facilitates the reaction channel of cyclization reaction, whereas that of electron-withdrawing groups inhibits this pathway. Copyright © 2015 John Wiley & Sons, Ltd.

Search for Compounds with Hypoglycemic Activity in the Series of 1-[2-(1H-Tetrazol-5-yl)-R1-phenyl]-3-R2-phenyl(ethyl)ureas and R1-Tetrazolo[1,5-c]quinazolin-5(6H)-ones

PubMed Central

Antypenko, Oleksii M.; Kovalenko, Sergiy I.; Zhernova, Galina O.

2016-01-01

Methods of 1-[2-(1H-tetrazol-5-yl)-R1-phenyl]-3-R2-phenyl(ethyl)ureas and R1-tetrazolo[1,5-c]quinazolin-5(6H)-ones synthesis were designed. IR, LC-MS, 1H NMR, and elemental analysis data evaluated the structure and purity of the obtained compounds. Different products, depending on the reaction conditions, were distinguished and discussed. The preliminary hypoglycemic activity of 36 synthesized compounds was revealed. Docking studies to 11β-hydroxysteroid dehydrogenase 1, γ-peroxisome proliferator-activated receptor, and dipeptidyl peptidase-4 were conducted. Eight of these substances were further tested on glucocorticoid-induced insulin resistance models, namely glucose tolerance, oral rapid insulin, and adrenalin tests. One of the most active compounds turned out to be tetrazolo[1,5-c]quinazolin-5(6H)-one 3.1, exceeding the reference drugs Metformin (50 and 200 mg/kg) and Gliclazide (50 mg/kg). PMID:27222601

Novel 4-Thiazolidinone Derivatives as Anti-Infective Agents: Synthesis, Characterization, and Antimicrobial Evaluation.

PubMed

Gupta, Amit; Singh, Rajendra; Sonar, Pankaj K; Saraf, Shailendra K

2016-01-01

A series of new 4-thiazolidinone derivatives was synthesized, characterized by spectral techniques, and screened for antimicrobial activity. All the compounds were evaluated against five Gram-positive bacteria, two Gram-negative bacteria, and two fungi, at concentrations of 50, 100, 200, 400, 800, and 1600 µg/mL, respectively. Minimum inhibitory concentrations of all the compounds were also determined and were found to be in the range of 100-400 µg/mL. All the compounds showed moderate-to-good antimicrobial activity. Compounds 4a [2-(4-fluoro-phenyl)-3-(4-methyl-5,6,7,8-tetrahydro-quinazolin-2-yl)-thiazolidin-4-one] and 4e [3-(4,6-dimethyl-pyrimidin-2-yl)-2-(2-methoxy-phenyl)-thiazolidin-4-one] were the most potent compounds of the series, exhibiting marked antimicrobial activity against Pseudomonas fluorescens, Staphylococcus aureus, and the fungal strains. Thus, on the basis of results obtained, it may be concluded that synthesized compounds exhibit a broad spectrum of antimicrobial activity.

Synthesis and characterization of 3-acetoxy-2-methyl-N-(phenyl)benzamide and 3-acetoxy-2-methyl-N-(4- methylphenyl)benzamide

NASA Astrophysics Data System (ADS)

Kırca, Başak Koşar; Çakmak, Şükriye; Kütük, Halil; Odabaşoğlu, Mustafa; Büyükgüngör, Orhan

2018-01-01

This study treats about two successfully synthesized secondary amide compounds 3-Acetoxy-2-methyl-N-(phenyl)benzamide, I and 3-Acetoxy-2-methyl-N-(4-methylphenyl)benzamide, II. Compounds were characterized by FTIR, 1H NMR, 13C NMR and X-ray single crystal diffraction analysis techniques. Single crystal X-ray diffraction analyses show that while I crystallized in the orthorhombic system with space group Pbca, II crystallized in the triclinic system with space group P-1 and the asymmetric unit of II consists of two crystallographically independent molecules. Lattice constants are a = 7.9713 (3) Å, b = 9.5059 (3) Å, c = 37.1762 (2) Å, Z = 8 for I and a = 7.5579 (8) Å, b = 8.8601 (8) Å, c = 23.363 (3) Å, α = 97.011 (9) °, β = 96.932 (9)°, γ = 90.051 (8)°, Z = 4 for II. Crystallographic studies also show that the supramolecular structures were stabilized by intramolecular, intermolecular hydrogen bonds and Csbnd H … π interactions for both compounds. Characteristic amide bonds were observed in IR and NMR spectra.

Structural and optical properties of p-quaterphenyl thin films and application in organic/inorganic photodiodes

NASA Astrophysics Data System (ADS)

Attia, A. A.; Saadeldin, M. M.; Soliman, H. S.; Gadallah, A.-S.; Sawaby, K.

2016-12-01

Para-quaterpheny1 (p-4pheny1) thin films were deposited by the thermal evaporation method on glass/quartz substrates for structural and optical investigations. The XRD of p-4phenyl thin films showed that the as-deposited films have a monoclinic structure. The surface morphology of p-4phenyl thin film was studied using scanning electron microscope. The absorption spectrum of p-4phenyl thin film recorded in the wavelength range 200-2500 nm. Photoluminescence measurements revealed two emission peaks at 435 and 444 nm using N2-laser (337.8 nm). The energy gap obtained from the absorption and photoluminescence data was found to be 2.87 and 2.74 eV respectively with Stokes shift value of 0.13 eV. The current-voltage characteristics of p-4phenyl/p-Si heterojunction have been recorded in the dark and under illumination of laser (337.8 nm). Responsivity, Detectivity, External quantum efficiency and Response speed of (Au/p-4pheny1/p-Si/Al) photodetector have been determined using different laser sources at -1 V bias.

A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone.

PubMed

Dal Cason, T A

2001-06-15

Recently, tablets inscribed with the Mitsubishi 3-diamond logo, and sold as 3,4-methylenedioxymethamphetamine (MDMA), were found to contain p-methoxymethamphetamine (PMMA), a compound with MDMA-like effects. Shortly after this first submission, similarly inscribed tablets were encountered containing both PMMA and p-methoxyamphetamine (PMA). This second tablet composition has been implicated in several recent deaths in the US. Because two other positions are available for mono-methoxy substitution on the phenyl ring, it is essential that the correct identification be made for these compounds. Analytical data are supplied to enable differentiation of these ring isomers as well as the ketones that serve as their precursors.

Synthesis, spectroscopic and structural characterization of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine with theoretical calculations using density functional theory

NASA Astrophysics Data System (ADS)

İnkaya, Ersin; Dinçer, Muharrem; Şahan, Emine; Yıldırım, İsmail

2013-10-01

In this paper, we will report a combined experimental and theoretical investigation of the molecular structure and spectroscopic parameters (FT-IR, 1H NMR, 13C NMR) of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine. The compound crystallizes in the triclinic space group P-1 with Z = 2. The molecular geometry was also optimized using density functional theory (DFT/B3LYP) method with the 6-311G(d,p) and 6-311++G(d,p) basis sets in ground state and compared with the experimental data. All the assignments of the theoretical frequencies were performed by potential energy distributions using VEDA 4 program. Information about the size, shape, charge density distribution and site of chemical reactivity of the molecules has been obtained by mapping electron density isosurface with electrostatic potential (ESP). Also, non-linear optical properties of the title compound were performed at B3LYP/6-311++G(d,p) level. The theoretical results showed an excellent agreement with the experimental values.

Construction of a new Cu2+ coated wire ion selective electrode based on 2-((2-(2-(2-(2-hydroxy-5-methoxybenzylidene amino)phenyl)disufanyl)phenylimino)methyl)-4-methoxyphenol Schiff base.

PubMed

Shokrollahi, A; Abbaspour, A; Ghaedi, M; Haghighi, A Naghashian; Kianfar, A H; Ranjbar, M

2011-03-15

In this article a new coated platinum Cu(2+) ion selective electrode based on 2-((2-(2-(2-(2-hydroxy-5-methoxybenzylideneamino)phenyl)disufanyl)phenylimino) methyl)-4-methoxyphenol Schiff base (L(1)) as a new ionophore is described. This sensor has a wide linear range of concentration (1.2 × 10(-7)-1.0 × 10(-1) mol L(-1)) and a low detection limit of 9.8 × 10(-8) mol L(-1)of Cu(NO(3))(2). It has a Nernstian response with slope of 29.54 ± 1.62 mV decade(-1) and it is applicable in the pH range of 4.0-6.0 without any divergence in potential. The coated electrode has a short response time of approximately 9s and is stable at least for 3.5 months. The electrode shows a good selectivity for Cu(2+) ion toward a wide variety of metal ions. The proposed sensor was successfully applied for the determination of Cu(2+) ion in different real and environmental samples and as indicator electrode for potentiometric titration of Cu(2+) ion with EDTA. Copyright © 2010 Elsevier B.V. All rights reserved.

2-((Benzimidazol-2-yl)thio)-1-arylethan-1-ones: Synthesis, crystal study and cancer stem cells CD133 targeting potential.

PubMed

Abdel-Aziz, Hatem A; Ghabbour, Hazem A; Eldehna, Wagdy M; Al-Rashood, Sara T A; Al-Rashood, Khalid A; Fun, Hoong-Kun; Al-Tahhan, Mays; Al-Dhfyan, Abdullah

2015-11-02

In order to develop a potent anti-tumor agent that can target both cancer stem cells and the bulk of tumor cells, a series of 2-((benzimidazol-2-yl)thio)-1-arylethan-1-ones 5a-o was synthesized. All compounds were evaluated for their anti-proliferative activity towards colon HT-29 cancer cell line. In addition, their inhibitory effect against cell surface expression of CD133, a potent cancer stem cells (CSCs) marker, in the same cells was evaluated by flow cytometry at 10 μM. Compound 5l emerged as the most active anti-proliferative analog against HT-29 (IC50 = 18.83 ± 1.37 μM), that almost equipotent as 5-fluorouracil (IC50 = 15.83 ± 1.63 μM) with 50.11 ± 4.05% inhibition effect on CD133 expression, suggested dual targeted effect. Also, compounds 5h, 5j, 5k and 5m-o inhibited the expression of CD133 with more than 50%. The SAR study pointed out the significance of substitution of the pendent phenyl group with lipophilic electron-donating groups or replacing it by 2-thienyl or 2-furyl groups. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

Density Functional Study on A-Units Based on Thieno[3,4- c]pyrrole-4,6-dione for Organic Solar Cells

NASA Astrophysics Data System (ADS)

Tang, Xiaoqin; Shen, Wei; Fu, Zhiyong; Liu, Xiaorui; Li, Ming

2017-08-01

The use of polymer donor materials has allowed great progress in organic solar cells. To search for potential donor materials, we have designed a series of donor-acceptor (D-A)-type alternating polymers composed of dithieno[3,2- b:2',3'- d]pyrrole (DTP) electron-rich units and thieno[3,4- c]pyrrole-4,6-dione (TPD) electron-deficient units. Their electronic and optical properties have been investigated using density functional theory and Marcus theory. The calculation results demonstrate that introduction of cyclic compounds (furyl, thienyl, and phenyl) into electron-deficient units of the molecules can result in lower highest occupied molecular orbital (HOMO) levels and reorganization energies compared with the experimental molecule ( X 0 ). To investigate the effects of electron-withdrawing units, three electron-withdrawing substituents (-OCH3, -F, and -CN) were introduced into the thienyl. The results indicated that the polymer X 2-3 will show the best performance among the designed polymers, offering low-lying HOMO energy level (-5.47 eV), narrow energy gap (1.97 eV), and high hole mobility (7.45 × 10-2 cm2 V-1 s-1). This work may provide a guideline for the design of efficient D-A polymers for organic solar cells with enhanced performance.

Prophylactic efficacy of S-2(2-aminoethylamino)ethyl phenyl sulfide (DRDE-07) against sulfur mustard induced lung toxicity in mice.

PubMed

Kannan, G M; Kumar, Pravin; Bhaskar, A S B; Pathak, U; Kumar, Deo; Nagar, D P; Pant, S C; Ganesan, K

2016-01-01

The present study was planned to investigate the prophylactic efficacy of S-2(2-aminoethylamino)ethyl phenyl sulfide (DRDE-07), against topically applied SM induced pulmonary toxicity in mouse. Animals were pretreated with S-2(2-aminoethylamino)ethyl phenyl sulfide (DRDE-07) (249.4 mg/kg by oral gavage) 30 minutes before SM exposure. The SM (6.48 mg/kg) was applied on hair clipped dorsocaudal region (percutaneous) of the animal. The animals were sacrificed on day 1, 3, 5 and 7. The biochemical changes those were observed in the bronchoalveolar lavage (BAL) fluid and lung tissue included protein, LDH, MPO, β-glucuronidase, MMP-2, MMP-9, activated macrophages, reduced glutathione and lipid peroxidation level. Pretreatment with DRDE-07 (0.2 LD50) attenuated SM-induced changes at all time point tested. BAL fluid biochemical endpoints indicated epithelial and endothelial cell damages as evidenced by increase in BAL protein, LDH level and increased number of activated macrophages. The increased myeloperoxidase activity and β-glucuronidase level exhibited the degranulation of neutrophils due to SM toxicity in lung. The zymogrphy analysis of BAL fluid showed a significant increase in matrix metalloproteases (MMP) activity due to inflammatory cells accumulation. Thirty minutes pretreatment with DRDE-07 decreased vascular permeability reduced the inflammation and oxidative stress, hence may be recommended as a potential prophylactic agent for SM intoxication.

DPPC/poly(2-methyl-2-oxazoline)-grad-poly(2-phenyl-2-oxazoline) chimeric nanostructures as potential drug nanocarriers

NASA Astrophysics Data System (ADS)

Pippa, Natassa; Kaditi, Eleni; Pispas, Stergios; Demetzos, Costas

2013-06-01

In this study, we report on the self assembly behavior and on stability studies of mixed (chimeric) nanosystems consisting of dipalmitoylphosphatidylcholine (DPPC) and poly(2-methyl-2-oxazoline)-grad-poly(2-phenyl-2-oxazoline) (MPOx) gradient copolymer in aqueous media and in fetal bovine serum (FBS). A gamut of light scattering techniques and fluorescence spectroscopy were used in order to extract information on the size and morphological characteristics of the nanoassemblies formed, as a function of gradient block copolymer content, as well as temperature. The hydrodynamic radii ( R h) of nanoassemblies decreased in the process of heating up to 50 °C, while the fractal dimension ( d f) values, also increased. Indomethacin was successfully incorporated into these chimeric nanocarriers. Drug release was depended on the components ratio. The present studies show that there are a number of parameters that can be used in order to alter the properties of chimeric nanosystems, and this is advantageous to the development of "smart" nanocarriers for drug delivery.

Yellow emitting Iridium (III) phenyl-benzothiazole complexes with different β-diketone ancillary ligands as dopants in white organic light-emitting diodes

NASA Astrophysics Data System (ADS)

Ivanov, P.; Petrova, P.; Tomova, R.

2018-03-01

We discuss the influence of the type of β-diketone ancillary ligand in Iridium (III) bis phenyl-benzothiazole complexes ((bt)2Ir(β-diketone)) on their photophysical and electroluminescent properties when they are used as dopants in white organic light-emitting diodes (WOLED). For this purpose, we investigated four novel yellow cyclometalated complexes: (bt)2Ir(dbm), (bt)2Ir(fmtdbm), (bt)2Ir(tta) and (bt)2Ir(bsm), where dbm = 1,3-diphenylpropane-1,3-dionate; fmtdbm = 1-(4-fluorophenyl)-3-(4-methoxyphenyl)propane-1,3-dionate; tta = 4,4,4-trifluoro-1-(thiophene-2-yl)butane-1,3-dionate; and bsm = 1-phenylicosane-1,3-dionate). To obtain white light by mixing emissions of two complementary colors (yellow emitted by the dopant and blue, by another emitter), we chose the following OLED structure: ITO/doped HTL/ElL/ETL/M, where ITO was a transparent anode of In2O3:SnO2; M, a metallic Al cathode; HTL, 4,4’-Bis(9H-carbazol-9-yl)biphenyl (CBP) involved in a poly(N-vinylcarbazole) (PVK) matrix; ElL, an electroluminescent layer of aluminum(III)bis(2-methyl-8-quninolinato)-4-phenylphenolate (BAlq); and ETL, an electron-transporting layer of zinc(II)bis(2-2-hydroxyphenyl)benzothiazole. We found that all complexes are suitable candidates for fabrication of WOLED. The best results were demonstrated by the device doped with 2 wt % of (bt)2Ir(bsm), which had twice as high luminescence (1100 cd/m2) and one-and-a-half as high current efficiency (5 cd/A) as the device doped with 1.25 wt % of the known (bt)2Ir(acac), with its 580 cd/m2 and 3.4 cd/A at approximately the same CIE (Commission Internationale de L’Eclairage) (x/y) coordinates of the warm white light emitted by the two devices.

Spectroscopic and structural investigation of interaction of 5-mercapto-3-phenyl-1,3,4-thiadiazole-2-thione potassium salt with molecular iodine

NASA Astrophysics Data System (ADS)

Ivolgina, Victoria A.; Chernov'yants, Margarita S.

2018-06-01

The interest in the study of heteroaromatic thioamides which are known to exhibit antithyroid activity is stimulated by the variety and an unusual structure their complexes with molecular iodine. The directions of dithiones investigation are diversity enough, however a few works are devoted to the study them as the potential thyreostatics. The ability of 5-mercapto-3-phenyl-1,3,4-thiadiazole-2-thion potassium salt to form the outer-sphere charge-transfer complex in dilute chloroform solution, coordinating 2 iodine molecules has been studied by UV-vis spectroscopy (lgβ = 7.91). The compound of the 5,5‧-disulfanediylbis(3-phenyl-1,3,4-thiadiazole-2(3H)-thione) - product of irreversible oxidation of 5-mercapto-3-phenyl-1,3,4-thiadiazole-2-thione potassium salt has been isolated and characterized by X-ray diffraction. Intermolecular interactions between sulfur atoms are observed with very short interatomic distance, shorter than sum of van der Waals radii. The contact between heterocyclic sulfur and heterocyclic nitrogen is also slightly short - 3.169 Å (0.053 Å less than vdW radii sum). This investigation constitutes a starting point for study of novel antithyroid drugs in future.

Synthesis and Mossbauer spectroscopic studies of chemically oxidized ferrocenyl(phenyl)phosphines.

PubMed

Durfey, D A; Kirss, R U; Frommen, C; Feighery, W

The electrochemical potentials of Fc3-xPPhx, (1-3, x = 0-2) and (FcPPh)n (4) indicate that iodine should oxidize ferrocenyl(phenyl)phosphines. The molar conductivity of solutions of 1-3 increases sharply when the solutions are titrated with iodine, leveling off after the addition of > 2 equiv of oxidant, consistent with formation of 1:1 electrolytes. Diamagnetic salts 6-9 are observed upon addition of a benzene solution of iodine to a benzene solution of 1-4 at ambient temperature in ratios of I2/metallocene ranging from 1:1 to 2:1. Well-resolved 1H and 31P NMR spectra are obtained for 6-8. Absorptions assigned to the I3- anion dominate the UV-vis spectrum of 6-8, whereas characteristic absorptions for [Fc][I3] are absent. Mossbauer spectra of 7-9 reveal isomer shifts consistent with low-spin iron(II) in ferrocene derivatives rather than those in ferricenium ions. Small amounts of low-spin FeIII appear to be present in 6. Taken together, the results suggest that 6-9 are iodophosphonium salts and not ferricenium salts. Diferrocenyl(phenyl)phosphine oxide (5) reacts with iodine to produce a diamagnetic, dark solid 10. Low-spin FeII is observed at 77 and 293 K in the Mossbauer spectra of 10 with no evidence for oxidation of FeII to FeIII. Compound 10 is proposed to be a neutral complex between 5 and I2. Reactions between 5 and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) yield [Fc2P(=O)][DDQ]2 (11). Mossbauer spectroscopy of 11 indicates the presence of a mixture of low-spin FeII and low-spin FeIII at 77 K, suggesting that some electron transfer occurs from 5 to DDQ. The fraction of low-spin FeIII increases at room temperature.

Crystal structure of (2R*,3aR*)-2-phenyl-sulfonyl-2,3,3a,4,5,6-hexa-hydro-pyrrolo-[1,2-b]isoxazole.

PubMed

Hernández, Yaiza; Marcos, Isidro; Garrido, Narciso M; Sanz, Francisca; Diez, David

2017-01-01

The title compound, C 12 H 15 NO 3 S, was prepared by 1,3-dipolar cyclo-addition of 3,4-di-hydro-2 H -pyrrole 1-oxide and phenyl vinyl sulfone. In the mol-ecule, both fused five-membered rings display a twisted conformation. In the crystal, C-H⋯O hydrogen bonds link neighbouring mol-ecules, forming chains running parallel to the b axis.

Potential Activity of 3-(2-Chlorophenyl)-1-phenyl-propenonein Accelerating Wound Healing in Rats

PubMed Central

Dhiyaaldeen, Summaya M.; Alshawsh, Mohammed A.; Salama, Suzy M.; Alwajeeh, Nahla S. I.

2014-01-01

Wound healing involves inflammation followed by granular tissue development and scar formation. In this study, synthetic chalcone 3-(2-Chlorophenyl)-1-phenyl-propenone (CPPP) was investigated for a potential role in enhancing wound healing and closure. Twenty-four male rats were divided randomly into 4 groups: carboxymethyl cellulose (CMC) (0.2 mL), Intrasite gel, and CPPP (25 or 50 mg/mL). Gross morphology, wounds treatment with the CPPP, and Intrasite gel accelerate the rate of wound healing compared to CMC group. Ten days after surgery, the animals were sacrificed. Histological assessment revealed that the wounds treated with CPPP showed that wound closure site contained little amount of scar and the granulation tissue contained more collagen and less inflammatory cells than wound treated with CMC. This finding was confirmed with Masson's trichrome staining. The antioxidant defence enzymes catalase (CAT) and superoxide dismutase (SOD) were significantly increased in the wound homogenates treated with CPPP (P < 0.05) compared to CMC treated group. However, in the CPPP treatment group, lipid peroxidation (MDA) was significantly decreased (P < 0.05), suggesting that the CPPP also has an important role in protection against lipid peroxidation-induced skin injury after ten days of treatment with CPPP, which is similar to the values of cytokines TGF-β and TNF-α in tissue homogenate. Finally the administration of CPPP at a dosage of 25 and 50 mg/kg was suitable for the stimulation of wound healing. PMID:24587992

Phenyl substitution of cationic bis-cyclometalated iridium(iii) complexes for iTMC-LEECs.

PubMed

Suhr, Kristin J; Bastatas, Lyndon D; Shen, Yulong; Mitchell, Lauren A; Frazier, Gary A; Taylor, David W; Slinker, Jason D; Holliday, Bradley J

2016-11-28

A series of seven cationic bis-cyclometalated iridium(iii) complexes of the form [(C^N) 2 (N^N)Ir][PF 6 ] has been designed in order to examine the effect of bulky, hydrophobic phenyl substituents on the structure-property relationship of these ionic transition metal complexes (iTMCs) in light-emitting electrochemical cells (LEECs). Capping phenyl substituents on the cyclometalating and ancillary ligands allows for individual tuning of the HOMO and LUMO energy levels, respectively, yielding an emission range from yellow to red. The complexes in this series exhibit increased quantum yields, up to 70% higher than the unoptimized, archetypal [(2-phenylpyridine) 2 (2,2'-bipyridine)Ir][PF 6 ]. Among these, one complex, C3, was recently reported to produce devices with superior luminance and efficiency. Simultaneous measure of the series of complexes enabled the clear discernment of trends in device performance connected to fundamental structure-property relationships that elucidate the origin of enhanced luminance. In general, phenyl substitution of the 2-phenylpyridine ligands of the parent complex produced higher luminance and faster device response than phenyl substitution of the 2,2'-bipyridine ligand. Overall, complex design and device engineering produce competitive LEECs from simple, single-layer architectures. The synthesis, crystallographic, photophysical, and electrochemical properties of the iTMCs, along with the electroluminescence properties of the LEEC devices are reported herein.

Effects of p-(Trifluoromethoxy)benzyl and p-(Trifluoromethoxy)phenyl Molecular Architecture on the Performance of Naphthalene Tetracarboxylic Diimide-Based Air-Stable n-Type Semiconductors.

PubMed

Zhang, Dongwei; Zhao, Liang; Zhu, Yanan; Li, Aiyuan; He, Chao; Yu, Hongtao; He, Yaowu; Yan, Chaoyi; Goto, Osamu; Meng, Hong

2016-07-20

N,N'-Bis(4-trifluoromethoxyphenyl) naphthalene-1,4,5,8-tetracarboxylic acid diimide (NDI-POCF3) and N,N'-bis(4-trifluoromethoxybenzyl) naphthalene-1,4,5,8-tetracarboxylic acid diimide (NDI-BOCF3) have similar optical and electrochemical properties with a deep LUMO level of approximately 4.2 eV, but exhibit significant differences in electron mobility and molecular packing. NDI-POCF3 exhibits nondetectable charge mobility. Interestingly, NDI-BOCF3 shows air-stable electron transfer performance with enhanced mobility by increasing the deposition temperature onto the octadecyltrichlorosilane (OTS)-modified SiO2/Si substrates and achieves electron mobility as high as 0.7 cm(2) V(-1) s(-1) in air. The different mobilities of those two materials can be explained by several factors including thin-film morphology and crystallinity. In contrast to the poor thin-film morphology and crystallinity of NDI-POCF3, NDI-BOCF3 exhibits larger grain sizes and improved crystallinities due to the higher deposition temperature. In addition, the theoretical calculated transfer integrals of the intermolecular lowest unoccupied molecular orbital (LUMO) of the two materials further show that a large intermolecular orbital overlap of NDI-BOCF3 can transfer electron more efficiently than NDI-POCF3 in thin-film transistors. On the basis of fact that the theoretical calculations are consistent with the experimental results, it can be concluded that the p-(trifluoromethoxy) benzyl (BOCF3) molecular architecture on the former position of the naphthalene tetracarboxylic diimides (NDI) core provides a more effective way to enhance the intermolecular electron transfer property than the p-(trifluoromethoxy) phenyl (POCF3) group for the future design of NDI-related air-stable n-channel semiconductor.

(E)-3-[2-(4-Chloro­phenyl­sulfon­yl)vin­yl]-6-methyl-4H-chromen-4-one

PubMed Central

Ravi Kumar, R.; Krishnaiah, M.; Oo, Thanzaw; Kaung, Pho; Jagadeesh Kumar, N.

2009-01-01

In the title compound, C18H13ClO4S, the mean planes of the chloro­phenyl ring and the S—C=C—C chain are oriented at angles of 52.7 (2) and 51.3 (2)°, respectively, with respect to the sulfonyl (O=S=O) plane. The dihedral angle between the mean planes of the chloro­phenyl group and the benzopyran ring is 80.7 (1)°. The crystal structure is stabilized by two inter­molecular C—H⋯O inter­actions, forming centrosymmetrc dimers, which are linked via a second C—H⋯O inter­action into a chain structure. PMID:21578354

Copper(I) Complexes of N-(2-{[(2E)-2-(4-Nitrobenzylidenyl)Hydrazinyl]Carbonyl}Phenyl)Benzamide and Triphenylphosphine: Synthesis, Characterization and Luminescence Properties.

PubMed

Chavan, S S; Pawal, S B; More, M S; Willis, A C

2016-11-01

Copper(I) complexes of the formula [Cu(L)(PPh 3 ) 2 ]X (1-4) (X = Cl(1), ClO 4 (2), BF 4 (3) and PF 6 (4)) [where L = N-(2-{[(2E)-2-(4-nitrobenzylidenyl)hydrazinyl]carbonyl}phenyl)benzamide; PPh 3  = triphenylphosphine] have been prepared by the condensation of N-[2-(hydrazinocarbonyl)phenyl]benzamide with 4-nitrobenzaldehyde followed by the reaction with CuCl, [Cu(MeCN) 4 ]ClO 4 , [Cu(MeCN) 4 ]BF 4 and [Cu(MeCN) 4 ]PF 6 in presence of triphenylphosphine as a coligand. Complexes 1-4 were then characterized by elemental analyses, FTIR, UV-visible and 1 H NMR spectroscopy. Mononuclear copper(I) complexes 1-4 were formed with L in its keto form by involvement of azomethine nitrogen and the carbonyl oxygen along with two PPh 3 groups. A single crystal X-ray diffraction study of the representative complex [(Cu(L)(PPh 3 ) 2 ]CIO 4 (2) reveals a distorted tetrahedral geometry around Cu(I). Crystal data of (2): space group = C2/c, a = 42.8596 (9) Å, b = 14.6207 (3) Å, c = 36.4643 (7) Å, V = 20,653.7 (7) Å 3 , Z = 16. Complexes 1-4 exhibit quasireversible redox behaviour corresponding to a Cu(I)/Cu(II) couple. All complexes show blue-green emission as a result of fluorescence from an intra-ligand charge transition (ILCT), ligand to ligand charge transfer transition (LLCT) or mixture of both. Significant increase in size of the counter anion shows marked effect on quantum efficiency and lifetime of the complexes in solution.

2-Octyl thiophene based three ring mesogens: solid state (13)C NMR and XRD investigations.

PubMed

Veeraprakash, B; Lobo, Nitin P; Narasimhaswamy, T; Mandal, A B

2015-08-14

2-Octyl thiophene based three-ring mesogens namely 4-n-alkoxyphenyl 4-(5-n-octyl-2-thienyl)benzoates are synthesized by employing palladium acetate based direct arylation. The alkoxy terminal is varied with even carbons from C2 to C14 and enantiotropic polymesomorphism is noticed for all the homologs. Accordingly, phase sequence consisting of nematic, smectic A, smectic C and smectic B is seen for mesogens with terminal chains C6, C8, C10 and C12 on cooling the isotropic phase. For mesogens with C2, C4, C8 and C10 terminal alkoxy chains, the mesophase assignment from hot-stage optical microscopy and differential scanning calorimetry is further confirmed by variable temperature powder X-ray diffraction measurements. The appearance of smectic B phase is established by noticing sharp and intense peaks in both small-angle and wide-angle regions. For a representative mesogen, i.e. T10, high-resolution solid-state (13)C NMR investigations are carried out in all the phases, viz. nematic, smectic A, smectic C and smectic B phases. The orientational order parameters calculated from (13)C-(1)H dipolar couplings from 2D SAMPI-4 experiments are found to be 0.44, 0.67, 0.73 and 0.79 in nematic, smectic A, smectic C and smectic B mesophases for the center phenyl ring respectively. Remarkably, the thiophene order parameter in all mesophases is found to be higher than that of phenyl rings and is explained by considering the molecular shape, which has a terminal bend. Further, the mesogens are found to be photoemissive in chloroform solution with an emission band at ∼410 nm.

Gas Permeation Properties of Soluble Aromatic Polyimides Based on 4-Fluoro-4,4'-Diaminotriphenylmethane

PubMed Central

Guzmán-Lucero, Diego; Froylán Palomeque-Santiago, Jorge; Camacho-Zúñiga, Claudia; Ruiz-Treviño, Francisco Alberto; Guzmán, Javier; Galicia-Aguilar, Alberto; Aguilar-Lugo, Carla

2015-01-01

A series of new organic polyimides were synthesized from 4-fluoro-4'4"-diaminotriphenylmethane and four different aromatic dianhydrides through a one-step, high-temperature, direct polycondensation in m-cresol at 180–200 °C, resulting in the formation of high-molecular-weight polyimides (inherent viscosities ~ 1.0–1.3 dL/g). All the resulting polyimides exhibited good thermal stability with initial decomposition temperatures above 434 °C, glass-transition temperatures between 285 and 316 °C, and good solubility in polar aprotic solvents. Wide-angle X-ray scattering data indicated that the polyimides were amorphous. Dense membranes were prepared by solution casting and solvent evaporation to evaluate their gas transport properties (permeability, diffusivity, and solubility coefficients) toward pure hydrogen, helium, oxygen, nitrogen, methane, and carbon dioxide gases. In general, the gas permeability was increased as both the fractional free volume and d-spacing were also increased. A good combination of permeability and selectivity was promoted efficiently by the bulky hexafluoroisopropylidene and 4-fluoro-phenyl groups introduced into the polyimides. The results indicate that the gas transport properties of these films depend on both the structure of the anhydride moiety, which controls the intrinsic intramolecular rigidity, and the 4-fluoro-phenyl pendant group, which disrupts the intermolecular packing. PMID:28788041

Gas Permeation Properties of Soluble Aromatic Polyimides Based on 4-Fluoro-4,4'-Diaminotriphenylmethane.

PubMed

Guzmán-Lucero, Diego; Palomeque-Santiago, Jorge Froylán; Camacho-Zúñiga, Claudia; Ruiz-Treviño, Francisco Alberto; Guzmán, Javier; Galicia-Aguilar, Alberto; Aguilar-Lugo, Carla

2015-04-21

A series of new organic polyimides were synthesized from 4-fluoro-4'4"-diaminotriphenylmethane and four different aromatic dianhydrides through a one-step, high-temperature, direct polycondensation in m-cresol at 180-200 °C, resulting in the formation of high-molecular-weight polyimides (inherent viscosities ~ 1.0-1.3 dL/g). All the resulting polyimides exhibited good thermal stability with initial decomposition temperatures above 434 °C, glass-transition temperatures between 285 and 316 °C, and good solubility in polar aprotic solvents. Wide-angle X-ray scattering data indicated that the polyimides were amorphous. Dense membranes were prepared by solution casting and solvent evaporation to evaluate their gas transport properties (permeability, diffusivity, and solubility coefficients) toward pure hydrogen, helium, oxygen, nitrogen, methane, and carbon dioxide gases. In general, the gas permeability was increased as both the fractional free volume and d-spacing were also increased. A good combination of permeability and selectivity was promoted efficiently by the bulky hexafluoroisopropylidene and 4-fluoro-phenyl groups introduced into the polyimides. The results indicate that the gas transport properties of these films depend on both the structure of the anhydride moiety, which controls the intrinsic intramolecular rigidity, and the 4-fluoro-phenyl pendant group, which disrupts the intermolecular packing.

Synthesis, spectroscopic and structural characterization of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine with theoretical calculations using density functional theory.

PubMed

Inkaya, Ersin; Dinçer, Muharrem; Sahan, Emine; Yıldırım, Ismail

2013-10-01

In this paper, we will report a combined experimental and theoretical investigation of the molecular structure and spectroscopic parameters (FT-IR, (1)H NMR, (13)C NMR) of 5-benzoyl-4-phenyl-2-methylthio-1H-pyrimidine. The compound crystallizes in the triclinic space group P-1 with Z=2. The molecular geometry was also optimized using density functional theory (DFT/B3LYP) method with the 6-311G(d,p) and 6-311++G(d,p) basis sets in ground state and compared with the experimental data. All the assignments of the theoretical frequencies were performed by potential energy distributions using VEDA 4 program. Information about the size, shape, charge density distribution and site of chemical reactivity of the molecules has been obtained by mapping electron density isosurface with electrostatic potential (ESP). Also, non-linear optical properties of the title compound were performed at B3LYP/6-311++G(d,p) level. The theoretical results showed an excellent agreement with the experimental values. Copyright © 2013 Elsevier B.V. All rights reserved.

Spectroscopic and structural investigation of interaction of 5-mercapto-3-phenyl-1,3,4-thiadiazole-2-thione potassium salt with molecular iodine.

PubMed

Ivolgina, Victoria A; Chernov'yants, Margarita S

2018-06-15

The interest in the study of heteroaromatic thioamides which are known to exhibit antithyroid activity is stimulated by the variety and an unusual structure their complexes with molecular iodine. The directions of dithiones investigation are diversity enough, however a few works are devoted to the study them as the potential thyreostatics. The ability of 5-mercapto-3-phenyl-1,3,4-thiadiazole-2-thion potassium salt to form the outer-sphere charge-transfer complex in dilute chloroform solution, coordinating 2 iodine molecules has been studied by UV-vis spectroscopy (lgβ=7.91). The compound of the 5,5'-disulfanediylbis(3-phenyl-1,3,4-thiadiazole-2(3H)-thione) - product of irreversible oxidation of 5-mercapto-3-phenyl-1,3,4-thiadiazole-2-thione potassium salt has been isolated and characterized by X-ray diffraction. Intermolecular interactions between sulfur atoms are observed with very short interatomic distance, shorter than sum of van der Waals radii. The contact between heterocyclic sulfur and heterocyclic nitrogen is also slightly short - 3.169Å (0.053Å less than vdW radii sum). This investigation constitutes a starting point for study of novel antithyroid drugs in future. Copyright © 2018 Elsevier B.V. All rights reserved.

3,4-Dimethyl-1-phenyl­pyrano[2,3-c]pyrazol-6(1H)-one

PubMed Central

Ahmad, Neman; Tahir, M. Nawaz; Khan, Misbahul Ain; Ather, Abdul Qayyum; Khan, Muhammad Naeem

2011-01-01

In the title compound, C14H12N2O2, the dihedral angle between the phenyl ring and the 3,4-dimethyl­pyrano[2,3-c]pyrazol-6(1H)-one system is 7.28 (6)°. An intra­molecular C—H⋯O inter­action generates an S(6) ring. In the crystal, the mol­ecules are linked by C—H⋯O hydrogen bonds, forming C(8) chains. C–H⋯π and π–π inter­actions [centroid–centroid separation = 3.6374 (12) Å] further consolidate the packing. PMID:21754037

The Synthesis of 1-Phenyl-1,2,3,4-tetrahydroisoquinolines: An Undergraduate Organic Laboratory Experiment and Class Project.

ERIC Educational Resources Information Center

Letcher, R. M.; Sammes, M. P.

1985-01-01

Describes an undergraduate organic chemistry experiment (requiring three/four 3-hour laboratory sessions) involving a four-stage synthesis of 1-phenyl-1,2,3,4-tetrahydroisoquinolines via the Pictet-Spengler route. In addition, the experiment allows students to study the spectra and properties of aklaloid-like materials while completing several…

Novel L-Dopa and dopamine prodrugs containing a 2-phenyl-imidazopyridine moiety.

PubMed

Denora, Nunzio; Laquintana, Valentino; Lopedota, Angela; Serra, Mariangela; Dazzi, Laura; Biggio, Giovanni; Pal, Dhananjay; Mitra, Ashim K; Latrofa, Andrea; Trapani, Giuseppe; Liso, Gaetano

2007-07-01

The aim of this study was to gain insight into the feasibility of enhancing the delivery of L-Dopa and dopamine to the brain by linking these neurotransmitters and L-Dopa ethyl ester to 2-phenyl-3-carboxymethyl-imidazopyridine compounds giving rise to the so-called Dopimid compounds. A number of Dopimid compounds were synthesized and both stability and binding studies to dopaminergic and benzodiazepine receptors were performed. To evaluate whether Dopimid compounds are P-gp substrates, [(3)H]ritonavir uptake experiments and bi-directional transport studies on confluent MDCKII-MDR1 monolayers were carried out. The brain penetration properties of Dopimid compounds were estimated by the Clark's computational model and evaluated by investigation of their transport across BBMECs monolayers. The dopamine levels following the intraperitoneal administration of the selected Dopimid compounds were measured in vivo by using brain microdialysis in rat. Tested compounds were adequately stable in solution buffered at pH 7.4 but undergo faster cleavage in dilute rat serum at 37 degrees C. Receptor binding studies showed that Dopimid compounds are essentially devoid of affinity for dopaminergic and benzodiazepine receptors. [(3)H]ritonavir uptake experiments indicated that selected Dopimid compounds, like L-Dopa and dopamine hydrochloride, are not substrates of P-gp and it was also confirmed by bi-directional transport experiments across MDCKII-MDR1 monolayers. By Clark's model a significant brain penetration was deduced for L-Dopa ethyl ester and dopamine derivatives. Transport studies involving BBMECs monolayers indicated that some of these compounds should be able to cross the BBB. Interestingly, the rank order of apparent permeability (P (app)) values observed in these assays parallels that calculated by the computational approach. Brain microdialysis experiments in rat showed that intraperitoneal acute administration of some Dopimid compounds induced a dose-dependent increase

p-halo N4-phenyl substituted thiosemicarbazones: Crystal structure, supramolecular architecture, characterization and bio-assay of their Co(III) and Ni(II) complexes

NASA Astrophysics Data System (ADS)

Kotian, Avinash; Kumara, Karthik; Kamat, Vinayak; Naik, Krishna; Kokare, Dhoolesh G.; Nevrekar, Anupama; Lokanath, Neratur Krishnappagowda; Revankar, Vidyanand K.

2018-03-01

In the present work, three potential metal ion chelating ligands, p-halo N4-phenyl substituted thiosemicarbazones are synthesized and characterized. The molecular structure of all (E)-4-(4-halophenyl)-1-(3-hydroxyiminobutan-2-ylidene) thiosemicarbazones (halo = F/Cl/Br) are determined by single crystal X-ray diffraction method. All the molecules have crystallized in monoclinic crystal system with P21/n space group. The ligands show Csbnd H⋯S and Nsbnd H⋯S intermolecular interactions, which are responsible to form the supramolecular self-assemblies through R22(8), R22(12) and R22(14) ring motifs. Hirshfeld surface analysis is carried out to explore the intermolecular interactions. A series of Co(III) and Ni(II) mononuclear transition metal complexes derived from these ligands have been synthesized and characterized by various spectro-analytical methods. The metal to ligand stoichiometry has been found to be 1:2 in all the complexes. The synthesized compounds have been investigated for their in vitro antimicrobial potencies. The compounds are found to be more active than the standard used, in the case of E. coli and A. niger. Additionally, they are also screened for their in vitro antitubercular activity.

3-Phenyl-6-(2-pyrid­yl)-1,2,4,5-tetra­zine

PubMed Central

Chartrand, Daniel; Laverdière, François; Hanan, Garry

2008-01-01

The title compound, C13H9N5, is the first asymmetric diaryl-1,2,4,5-tetra­zine to be crystallographically characterized. We have been inter­ested in this motif for incorporation into supra­molecular assemblies based on coordination chemistry. The solid state structure shows a centrosymmetric mol­ecule, forcing a positional disorder of the terminal phenyl and pyridyl rings. The mol­ecule is completely planar, unusual for aromatic rings with N atoms in adjacent ortho positions. The stacking observed is very common in diaryl­tetra­zines and is dominated by π stacking [centroid-to-centroid distance between the tetrazine ring and the aromatic ring of an adjacent molecule is 3.6 Å, perpendicular (centroid-to-plane) distance of about 3.3 Å]. PMID:21200916

BF3·Et2O Catalysed 4-Aryl-3-phenyl-benzopyrones, Pro-SERMs, and Their Characterization

PubMed Central

Srivastava, Ambika; Kumar, Rajesh

2015-01-01

We have synthesized the novel 4-(4-hydroxy-benzyl)-3-phenyl-chromen-2-one which is a precursor of SERMs with a smaller number of steps and good yield. Two methodologies for the synthesis have been worked out. Anhydrous BF3·Et2O catalyzed reaction was found to be selective for product formation while anhydrous AlCl3, FeCl3, and SnCl4 catalyzed ones were nonselective. PMID:26421007

Three closely related 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridines: synthesis, molecular conformations and hydrogen bonding in zero, one and two dimensions.

PubMed

Sagar, Belakavadi K; Harsha, Kachigere B; Yathirajan, Hemmige S; Rangappa, Kanchugarakoppal S; Rathore, Ravindranath S; Glidewell, Christopher

2017-03-01

In each of 1-(4-fluorophenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine, C 21 H 19 F 4 N 3 O 2 S, (I), 1-(4-chlorophenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine, C 21 H 19 ClF 3 N 3 O 2 S, (II), and 1-(3-methylphenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine, C 22 H 22 F 3 N 3 O 2 S, (III), the reduced pyridine ring adopts a half-chair conformation with the methylsulfonyl substituent occupying an equatorial site. Although compounds (I) and (II) are not isostructural, having the space groups Pbca and P2 1 2 1 2 1 , respectively, their molecular conformations are very similar, but the conformation of compound (III) differs from those of (I) and (II) in the relative orientation of the N-benzyl and methylsulfonyl substituents. In compounds (II) and (III), but not in (I), the trifluoromethyl groups are disordered over two sets of atomic sites. Molecules of (I) are linked into centrosymmetric dimers by C-H...π(arene) hydrogen bonds, molecules of (II) are linked by two C-H...O hydrogen bonds to form ribbons of R 3 3 (18) rings, which are themselves further linked by a C-Cl...π(arene) interaction, and a combination of C-H...O and C-H...π(arene) hydrogen bonds links the molecules of (III) into sheets. Comparisons are made with the structures of some related compounds.

Miscibility and in vitro osteocompatibility of biodegradable blends of poly[(ethyl alanato) (p-phenyl phenoxy) phosphazene] and poly(lactic acid-glycolic acid)

PubMed Central

Deng, Meng; Nair, Lakshmi S.; Nukavarapu, Syam P.; Kumbar, Sangamesh G.; Jiang, Tao; Krogman, Nicholas R.; Singh, Anurima; Allcock, Harry R.; Laurencin, Cato T.

2007-01-01

Previously we demonstrated the ability of ethyl glycinato substituted polyphosphazenes to neutralize the acidic degradation products and control the degradation rate of poly(lactic acid-glycolic acid) by blending. In this study, blends of high strength poly[(50% ethyl alanato) (50% p-phenyl phenoxy) phosphazene] (PNEA50PhPh50) and 85:15 poly(lactic acid-glycolic acid) (PLAGA) were prepared using a mutual solvent approach. Three different solvents, methylene chloride (MC), chloroform (CF) and tetrahydrofuran (THF) were studied to investigate solvent effects on blend miscibility. Three different blends were then fabricated at various weight ratios namely 25:75 (BLEND25), 50:50 (BLEND50), and 75:25 (BLEND75) using THF as the mutual solvent. The miscibility of the blends was evaluated by scanning electron microscopy (SEM), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FTIR). Among these, BLEND25 was miscible while BLEND50 and BLEND75 were partially miscible. Furthermore, BLEND25 formed apatite layers on its surface as evidenced in a biomimetic study performed. These novel blends showed cell adhesion and proliferation comparable to PLAGA. However, the PNEA50PhPh50 component in the blends was able to increase the phenotypic expression and mineralized matrix synthesis of the primary rat osteoblasts (PRO) in vitro. Blends of high strength poly[(50% ethyl alanato) (50% p-phenyl phenoxy) phosphazene] (PNEA50PhPh50) and 85:15 poly(lactic acid-glycolic acid) (PLAGA) are promising biomaterials for a variety of musculoskeletal applications. PMID:17942150

Why Do Simple Molecules with "Isolated" Phenyl Rings Emit Visible Light?

PubMed

Zhang, Haoke; Zheng, Xiaoyan; Xie, Ni; He, Zikai; Liu, Junkai; Leung, Nelson L C; Niu, Yingli; Huang, Xuhui; Wong, Kam Sing; Kwok, Ryan T K; Sung, Herman H Y; Williams, Ian D; Qin, Anjun; Lam, Jacky W Y; Tang, Ben Zhong

2017-11-15

π-Bonds connected with aromatic rings were generally believed as the standard structures for constructing highly efficient fluorophores. Materials without these typical structures, however, exhibited only low fluorescence quantum yields and emitted in the ultraviolet spectral region. In this work, three molecules, namely bis(2,4,5-trimethylphenyl)methane, 1,1,2,2-tetrakis(2,4,5-trimethylphenyl)ethane, and 1,1,2,2-tetraphenylethane, with nonconjugated structures and isolated phenyl rings were synthesized and their photophysical properties were systematically investigated. Interestingly, the emission spectra of these three molecules could be well extended to 600 nm with high solid-state quantum yields of up to 70%. Experimental and theoretical analyses proved that intramolecular through-space conjugation between the "isolated" phenyl rings played an important role for this abnormal phenomenon.

Phenyl 3,5-di-tert-butyl-2-hy­droxy­benzoate

PubMed Central

Carreño, Alexander; Preite, Marcelo; Manriquez, Juan Manuel; Vega, Andrés; Chavez, Ivonne

2010-01-01

The title mol­ecule, C21H26O3, has a six-membered planar carbon ring as the central core, substituted at position 1 with phen­oxy­carbonyl, at position 2 with hy­droxy and at positions 3 and 5 with tert-butyl groups. The structure shows two independent but very similar mol­ecules within the asymmetric unit. For both independent mol­ecules, the ester carboxyl­ate group is coplanar with the central core, as reflected by the small C—C—O—C torsion angles [179.95 (17) and 173.70 (17)°]. In contrast, the phenyl substituent is almost perpendicular to the carboxyl­ate –CO2 fragment, as reflected by C—O—C—C torsion angles, ranging from 74 to 80°. The coplanarity between the central aromatic ring and the ester carboxyl­ate –CO2– group allows the formation of an intra­molecular hydrogen bond, with O⋯O distances of 2.563 (2) and 2.604 (2) Å. PMID:21589569

Excited state luminescence of multi-(5-phenyl-1,3,4-oxadiazo-2-yl)benzenes in an electron-donating matrix: exciplex or electroplex?

PubMed

Yang, Chih-Chiang; Hsu, Chia-Jung; Chou, Pi-Tai; Cheng, Hsu Chun; Su, Yuhlong Oliver; Leung, Man-kit

2010-01-21

Multi-(5-phenyl-1,3,4-oxadiazo-2-yl)benzenes show emission in organic solvents from ultraviolet to blue (339-447 nm). The reduction potentials E(1/2)(red) cover a large range of -2.11 V for 2,5-diphenyl-1,3,4-oxadiazole to -0.76 V for 1,2,3,4,5,6-hexa(5-phenyl-1,3,4-oxadiazo-2-yl)benzene. An unexpectedly wide spectral range of the oxadiazole (OXD) exciplex emissions in PVK is observed, ranging from 406 to 603 nm. The OXDs also exhibit similar electroluminescence (EL) when blended into polyvinylcarbazole (PVK). A linear correlation between the lambda(max) of the electroluminescence and photoluminescence is observed, implying that the emission mechanisms in both processes are similar. In addition, the linear correlation between the E(1/2)(red) versus lambda(max) of EL (eV) reflected that the term of the charge-transfer configuration of the contact electron-hole pair plays a major role in the exciplex emission. The exciplex EL of 1,2,5-tri(5-phenyl-1,3,4-oxadiazo-2-yl)benzene (5) could be as high as 1.0 cd/A. Since the exciplex emission usually has a large Stokes shift, this provides a window for us to generate duo emissions for near white light EL with high efficiency. Among the devices we tried, the device of PVK/2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole/5/2,5,8,11-tetra-tert-butylperylene (100:40:40:4) gave EL with good current efficiency of 1.63 cd/A.

Optically active antifungal azoles. XII. Synthesis and antifungal activity of the water-soluble prodrugs of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone.

PubMed

Ichikawa, T; Kitazaki, T; Matsushita, Y; Yamada, M; Hayashi, R; Yamaguchi, M; Kiyota, Y; Okonogi, K; Itoh, K

2001-09-01

1-[(1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (1: TAK-456) was selected as a candidate for clinical trials, but since its water-solubility was insufficient for an injectable formulation, the quaternary triazolium salts 2 were designed as water-soluble prodrugs. Among the prodrugs prepared, 4-acetoxymethyl-1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-1-terazolyl)phenyl]-1-imidazolidinyl]butyl]-1H-1,2,4-triazolium chloride (2a: TAK-457) was selected as an injectable candidate for clinical trials based on the results of evaluations on solubility, stability, hemolytic effect and in vivo antifungal activities.

Pretreatment with nomifensine or nomifensine analogue 4-phenyl-1,2,3,4-tetrahydroisoquinoline augments methamphetamine-induced stereotypical behavior in mice

PubMed Central

Hall, F. Scott; Uhl, George R.; Asano, Hiromi; Chatani, Ryuki; Hayata, Sachiko; Yokoyama, Hiroko; Tanaka, Koh-ichi; Nishiyama, Nobuyoshi; Takemura, Motohiko

2014-01-01

Nomifensine is a dopamine/norepinephrine reuptake inhibitor. Nomifensine and some of its structural analogues produce behavioral effects indicative of indirect dopaminergic agonist properties, such as hyperlocomotion. By contrast, the deaminated and demethylated nomifensine analogue 4-phenyl-1,2,3,4-tetrahydroisoquinoline (PTIQ) is reported to have amphetamine-antagonistic properties, as demonstrated by inhibition of methamphetamine (METH)-induced dopamine release in the nucleus accumbens and METH-induced hyperlocomotion in rats. In the present study, we examined the effect of PTIQ (10 mg/kg, i.p.) and nomifensine (3 mg/kg, i.p.) on METH (5 or 10 mg/kg ,i.p.)-induced stereotypical behavior in mice in order to determine whether PTIQ and nomifensine inhibit and augment, respectively, METH-induced stereotypical behavior. Unexpectedly, our observations demonstrated that both PTIQ and nomifensine significantly augmented METH-induced stereotypical behavior and locomotion in mice. This augmentation is likely the result of additive effects on dopaminergic function by METH in combination with PTIQ or nomifensine. These results suggest that, contrary to some reports, PTIQ may display dopaminergic agonist properties in mice. PMID:22265332

40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

Code of Federal Regulations, 2013 CFR

2013-07-01

... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new uses...

40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new uses...

40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new uses...

40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new uses...

40 CFR 721.4840 - Substituted tri-phenyl-meth-ane.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Substituted tri-phenyl-meth-ane. 721.4840 Section 721.4840 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC... Substances § 721.4840 Substituted tri-phenyl-meth-ane. (a) Chemical substance and significant new uses...

Synergistic effects of influenza and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) can be eliminated by the use of influenza therapeutics: experimental evidence for the multi-hit hypothesis.

PubMed

Sadasivan, Shankar; Sharp, Bridgett; Schultz-Cherry, Stacey; Smeyne, Richard Jay

2017-01-01

Central Nervous System inflammation has been implicated in neurodegenerative disorders including Parkinson's disease (Ransohoff, Science 353: 777-783, 2016; Kannarkat et al. J. Parkinsons Dis. 3: 493-514, 2013). Here, we examined if the H1N1 influenza virus (Studahl et al. Drugs 73: 131-158, 2013) could synergize with the parkinsonian toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (Jackson-Lewis et al. in Mark LeDoux (ed) Movement Disorders: Genetics and Models : 287-306, Elsevier, 2015) to induce a greater microglial activation and loss of substantia nigra pars compacta dopaminergic neurons than either insult alone. H1N1-infected animals administered 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine exhibit a 20% greater loss of substantia nigra pars compacta dopaminergic neurons than occurs from the additive effects of H1N1 or 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine alone ( p  < 0.001). No synergistic effects were found in microglial activation. The synergistic dopaminergic neuron loss is eliminated by influenza vaccination or treatment with oseltamivir carboxylate. This work shows that multiple insults can induce synergistic effects; and even these small changes can be significant as it might allow one to cross a phenotypic disease threshold that would not occur from individual non-interacting exposures. Our observations also have important implications for public health, providing impetus for influenza vaccination or prompt treatment with anti-viral medications upon influenza diagnosis.

Plasticity of Cl-Te-Cl Fragments. Synthesis, Single-Crystal X-ray, and NBO Study of (1-Thia-2-tellura-1-phenyl-4-chloro)cyclopentane 2,2,2-Trichloride.

PubMed

Sundberg, Markku R.; Laitalainen, Tarja; Bergman, Jan; Uggla, Rolf; Matikainen, Jorma; Kaltia, Seppo

1998-06-01

Tellurium tetrachloride and allylphenyl sulfide react to form (1-thia-2-tellura-1-phenyl-4-chloro)cyclopentane 2,2,2-trichloride. The crystal and molecular structure were determined by single-crystal X-ray techniques. The crystals belong to the monoclinic system, space group P2(1)/c (No. 14) with a = 6.020(3) Å, b = 11.46(1) Å, c = 20.156(2) Å, beta = 97.53(2) degrees, V = 1379(1) Å(3), and Z = 4. The structure was refined to the final R value of 0.036. The coordination around Te(IV) is distorted psi octahedral with three Cl atoms in the equatorial positions. The axial Te(1)-C(1) bond opposite to the lone pair of electrons at the Te(IV) atom completes the coordination polyhedron. The intramolecular Te-S distance is 2.903(3) Å. Symmetric and asymmetric deformation modes were established to describe the plasticity of the Cl-Te-Cl fragments extracted from the Cambridge Structural Database. The hypervalency of Te(IV) manifests itself as plasticity in the equatorial plane of the coordination sphere. The NBO calculations show that all of the equatorial Te-Cl bonds are highly polarized and the electrons reside mainly on the Cl atoms.

Design and synthesis of some new 1-phenyl-3/4-[4-(aryl/heteroaryl/alkyl-piperazine1-yl)-phenyl-ureas as potent anticonvulsant and antidepressant agents.

PubMed

Mishra, Chandra Bhushan; Kumari, Shikha; Tiwari, Manisha

2016-05-01

A series of 1-phenyl-3/4-[4-(aryl/heteroaryl/alkyl-piperazine1-yl)-phenyl-urea derivatives (29-42) were designed, synthesized and evaluated for their anticonvulsant activity by using maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) seizure tests. The acute neurotoxicity was checked by rotarod assay. Most of the test compounds were found effective in both seizure tests. Compound 30 (1-{4-[4-(4-chloro-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-urea) exhibited marked anticonvulsant activity in MES as well as scPTZ tests. The phase II anticonvulsant quantification study of compound 30 indicates the ED50 value of 28.5 mg/kg against MES induced seizures. In addition, this compound also showed considerable protection against pilocarpine induced status epilepticus in rats. Seizures induced by 3-mercaptopropionic acid model and thiosemicarbazide were significantly attenuated by compound 30, which suggested its broad spectrum of anticonvulsant activity. Interestingly, compound 30 displayed better antidepressant activity than standard drug fluoxetine. Moreover, compound 30 appeared as a non-toxic chemical entity in sub-acute toxicity studies.

Controlling the Conformational Energy of a Phenyl Group by Tuning the Strength of a Nonclassical CH···O Hydrogen Bond: The Case of 5-Phenyl-1,3-dioxane.

PubMed

Bailey, William F; Lambert, Kyle M; Stempel, Zachary D; Wiberg, Kenneth B; Mercado, Brandon Q

2016-12-16

Anancomeric 5-phenyl-1,3-dioxanes provide a unique opportunity to study factors that control conformation. Whereas one might expect an axial phenyl group at C(5) of 1,3-dioxane to adopt a conformation similar to that in axial phenylcyclohexane, a series of studies including X-ray crystallography, NOE measurements, and DFT calculations demonstrate that the phenyl prefers to lie over the dioxane ring in order to position an ortho-hydrogen to participate in a stabilizing, nonclassical CH···O hydrogen bond with a ring oxygen of the dioxane. Acid-catalyzed equilibration of a series of anancomeric 2-tert-butyl-5-aryl-1,3-dioxane isomers demonstrates that remote substituents on the phenyl ring affect the conformational energy of a 5-aryl-1,3-dioxane: electron-withdrawing substituents decrease the conformational energy of the aryl group, while electron-donating substituents increase the conformational energy of the group. This effect is correlated in a very linear way to Hammett substituent parameters. In short, the strength of the CH···O hydrogen bond may be tuned in a predictable way in response to the electron-withdrawing or electron-donating ability of substituents positioned remotely on the aryl ring. This effect may be profound: a 3,5-bis-CF 3 phenyl group at C(5) in 1,3-dioxane displays a pronounced preference for the axial orientation. The results are relevant to broader conformational issues involving heterocyclic systems bearing aryl substituents.

40 CFR 721.5286 - Benzenediazonium, [[[[(substituted) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol...

Code of Federal Regulations, 2010 CFR

2010-07-01

...) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized..., [[[[(substituted) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized..., [[[[(substituted)azo]phenyl]sulfonyl]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized...

40 CFR 721.5286 - Benzenediazonium, [[[[(substituted) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol...

Code of Federal Regulations, 2011 CFR

2011-07-01

...) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized..., [[[[(substituted) azo]phenyl]sulfonyl]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized..., [[[[(substituted)azo]phenyl]sulfonyl]amino]-, coupled with aminophenol, diazotized aminobenzoic acid, diazotized...

Conformation and tautomerism of methoxy-substituted 4-phenyl-4-thiazoline-2-thiones: a combined crystallographic and ab initio investigation.

PubMed

Balti, Monaem; Norberg, Bernadette; Efrit, Mohamed Lotfi; Lanners, Steve; Wouters, Johan

2016-05-01

4-Phenyl-4-thiazoline-2-thiol is an active pharmaceutical compound, one of whose activities is as a human indolenamine dioxygenase inhibitor. It has been shown recently that in both the solid state and the gas phase, the thiazolinethione tautomer should be preferred. As part of both research on this lead compound and a medicinal chemistry program, a series of substituted arylthiazolinethiones have been synthesized. The molecular conformations and tautomerism of 4-(2-methoxyphenyl)-4-thiazoline-2-thione and 4-(4-methoxyphenyl)-4-thiazoline-2-thione, both C10H9NOS2, are reported and compared with the geometry deduced from ab initio calculations [PBE/6-311G(d,p)]. Both the crystal structure analyses and the calculations establish the thione tautomer for the two substituted arylthiazolinethiones. In the crystal structure of the 2-methoxyphenyl regioisomer, the thiazolinethione unit was disordered over two conformations. Both isomers exhibit similar hydrogen-bond patterns [R2(2)(8) motif] and form dimers. The crystal packing is further reinforced by short S...S interactions in the 2-methoxyphenyl isomer. The conformations of the two regioisomers correspond to stable geometries calculated from an ab initio energy-relaxed scan.

Duplex and triplex formation of mixed pyrimidine oligonucleotides with stacking of phenyl-triazole moieties in the major groove.

PubMed

Andersen, Nicolai Krog; Døssing, Holger; Jensen, Frank; Vester, Birte; Nielsen, Poul

2011-08-05

5-(1-Phenyl-1,2,3-triazol-4-yl)-2'-deoxycytidine was synthesized from a modified CuAAC protocol and incorporated into mixed pyrimidine oligonucleotide sequences together with the corresponding 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridine. With consecutive incorporations of the two modified nucleosides, improved duplex formation with a complementary RNA and improved triplex formation with a complementary DNA duplex were observed. The improvement is due to π-π stacking of the phenyl-triazole moieties in the major groove. The strongest stacking and most pronounced positive influence on thermal stability was found in between the uridine analogues or with the cytidine analogue placed in the 3' direction to the uridine analogue. Modeling indicated a different orientation of the phenyl-triazole moieties in the major groove to account for the difference between the two nucleotides. The modified oligonucleotides were all found to be significantly stabilized toward nucleolytic degration.

Calculation of Hammett Equation parameters for some N,N‧-bis (substituted-phenyl)-1,4-quinonediimines by density functional theory

NASA Astrophysics Data System (ADS)

Sein, Lawrence T.

2011-08-01

Hammett parameters σ' were determined from vertical ionization potentials, vertical electron affinities, adiabatic ionization potentials, adiabatic electron affinities, HOMO, and LUMO energies of a series of N, N' -bis (3',4'-substituted-phenyl)-1,4-quinonediimines computed at the B3LYP/6-311+G(2d,p) level on B3LYP/6-31G ∗ molecular geometries. These parameters were then least squares fit as a function of literature Hammett parameters. For N, N' -bis (4'-substituted-phenyl)-1,4-quinonediimines, the least squares fits demonstrated excellent linearity, with the square of Pearson's correlation coefficient ( r2) greater than 0.98 for all isomers. For N, N' -bis (3'-substituted-3'-aminophenyl)-1,4-quinonediimines, the least squares fits were less nearly linear, with r2 approximately 0.70 for all isomers when derived from calculated vertical ionization potentials, but those from calculated vertical electron affinities usually greater than 0.90.

Bis(4-(3,4-dimethylenepyrrolidyl)-phenyl) methane

NASA Technical Reports Server (NTRS)

Ottenbrite, Raphael M. (Inventor)

1989-01-01

It is the primary object of the present invention to prepare high temperature polymeric materials, especially linear aromatic polyimides, which maintain their integrity and toughness during long exposure times at elevated temperatures. According to the present invention, this object is achieved, and the attending benefits are obtained, by first providing the bis(exocyclodiene) bis(4-(3,4-dinethylene pyrrolidyl) phenyl) methane, which is formed from the monomer N-phenyl 3,4-dimethylene pyrrolidine. This bis-(exocyclodiene) undergoes Diels-Alder reaction with a bismaleimide without the evolution of gaseous by-products, to form the aromatic polyimide.

(Z)-3-(1-Chloro-prop-1-en-yl)-2-methyl-1-phenyl-sulfonyl-1H-indole.

PubMed

Umadevi, M; Saravanan, V; Yamuna, R; Mohanakrishnan, A K; Chakkaravarthi, G

2013-11-16

In the title compound, C18H16ClNO2S, the indole ring system forms a dihedral angle of 75.07 (8)° with the phenyl ring. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming a chain along [10-1]. C-H⋯π inter-actions are also observed, leading to a three-dimensional network.

Bis(N'-{(E)-[(2E)-1,3-di-phenyl-prop-2-en-1-yl-idene]amino}-N-ethyl-carbamimido-thio-ato-κ2N',S)zinc(II): crystal structure and Hirshfeld surface analysis.

PubMed

Tan, Ming Yueh; Crouse, Karen A; Ravoof, Thahira B S A; Jotani, Mukesh M; Tiekink, Edward R T

2017-07-01

The title Zn II complex, [Zn(C 18 H 18 N 3 S) 2 ], (I), features two independent but chemically equivalent mol-ecules in the asymmetric unit. In each, the thio-semicarbazonate monoanion coordinates the Zn II atom via the thiol-ate-S and imine-N atoms, with the resulting N 2 S 2 donor set defining a distorted tetra-hedral geometry. The five-membered ZnSCN 2 chelate rings adopt distinct conformations in each independent mol-ecule, i.e. one ring is almost planar while the other is twisted about the Zn-S bond. In the crystal, the two mol-ecules comprising the asymmetric unit are linked by amine-N-H⋯N(imine) and amine-N-H⋯S(thiol-ate) hydrogen bonds via an eight-membered heterosynthon, {⋯HNCN⋯HNCS}. The dimeric aggregates are further consolidated by benzene-C-H⋯S(thiol-ate) inter-actions and are linked into a zigzag supra-molecular chain along the c axis via amine-N-H⋯S(thiol-ate) hydrogen bonds. The chains are connected into a three-dimensional architecture via phenyl-C-H⋯π(phen-yl) and π-π inter-actions, the latter occurring between chelate and phenyl rings [inter-centroid separation = 3.6873 (11) Å]. The analysis of the Hirshfeld surfaces calculated for (I) emphasizes the different inter-actions formed by the independent mol-ecules in the crystal and the impact of the π-π inter-actions between chelate and phenyl rings.

Understanding the scale of the single ion free energy: A critical test of the tetra-phenyl arsonium and tetra-phenyl borate assumption

NASA Astrophysics Data System (ADS)

Duignan, Timothy T.; Baer, Marcel D.; Mundy, Christopher J.

2018-06-01

The tetra-phenyl arsonium and tetra-phenyl borate (TATB) assumption is a commonly used extra-thermodynamic assumption that allows single ion free energies to be split into cationic and anionic contributions. The assumption is that the values for the TATB salt can be divided equally. This is justified by arguing that these large hydrophobic ions will cause a symmetric response in water. Experimental and classical simulation work has raised potential flaws with this assumption, indicating that hydrogen bonding with the phenyl ring may favor the solvation of the TB- anion. Here, we perform ab initio molecular dynamics simulations of these ions in bulk water demonstrating that there are significant structural differences. We quantify our findings by reproducing the experimentally observed vibrational shift for the TB- anion and confirm that this is associated with hydrogen bonding with the phenyl rings. Finally, we demonstrate that this results in a substantial energetic preference of the water to solvate the anion. Our results suggest that the validity of the TATB assumption, which is still widely used today, should be reconsidered experimentally in order to properly reference single ion solvation free energy, enthalpy, and entropy.

Comparative XAFS studies of some Cobalt complexes of (3-N- phenyl -thiourea-pentanone-2)

NASA Astrophysics Data System (ADS)

soni, Namrata; Parsai, Neetu; Mishra, Ashutosh

2016-10-01

XAFS spectroscopy is a useful method for determining the local structure around a specific atom in disordered systems. XAFS study of some cobalt complexes of (3-N-phenyle- thiourea-pentanon-2) is carried out using the latest XAFS analysis software Demeter with Strawberry Perl. The same study is also carried out theoretically using Mathcad software. It is found that the thiourea has significant influence in the spectra and the results obtained experimentally and theoretically are in agreement. Fourier transform of the experimental and theoretically generated XAFS have been taken to obtain first shell radial distance. The values so obtained are in agreement with each other.

Fast Hetero-Diels-Alder Reactions Using 4-Phenyl-1,2,4-Triazoline-3,5-Dione (PTAD) as the Dienophile

ERIC Educational Resources Information Center

Celius, Tevye C.

2010-01-01

A hetero-Diels-Alder reaction that proceeds rapidly and only requires a simple filtration to purify the product is presented. The dienophile, 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), is prepared by the heterogeneous oxidation of 4-phenylurazole by the bromenium ion, Br[superscript +], generated in situ by the oxidation of potassium bromide by…

Three closely related (2E,2'E)-3,3'-(1,4-phenyl-ene)bis-[1-(meth-oxy-phen-yl)prop-2-en-1-ones]: supra-molecular assemblies in one dimension mediated by hydrogen bonding and C-H⋯π inter-actions.

PubMed

Sim, Aijia; Chidan Kumar, C S; Kwong, Huey Chong; Then, Li Yee; Win, Yip-Foo; Quah, Ching Kheng; Naveen, S; Chandraju, S; Lokanath, N K; Warad, Ismail

2017-06-01

In the title compounds, (2 E ,2' E )-3,3'-(1,4-phenyl-ene)bis-[1-(2-meth-oxy-phen-yl)prop-2-en-1-one], C 26 H 22 O 4 (I), (2 E ,2' E )-3,3'-(1,4-phenyl-ene)bis-[1-(3-meth-oxy-phen-yl)prop-2-en-1-one], C 26 H 22 O 4 (II) and (2 E ,2' E )-3,3'-(1,4-phenyl-ene)bis-[1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one], C 28 H 26 O 6 (III), the asymmetric unit consists of a half-mol-ecule, completed by crystallographic inversion symmetry. The dihedral angles between the central and terminal benzene rings are 56.98 (8), 7.74 (7) and 7.73 (7)° for (I), (II) and (III), respectively. In the crystal of (I), mol-ecules are linked by pairs of C-H⋯π inter-actions into chains running parallel to [101]. The packing for (II) and (III), features inversion dimers linked by pairs of C-H⋯O hydrogen bonds, forming R 2 2 (16) and R 2 2 (14) ring motifs, respectively, as parts of [201] and [101] chains, respectively.

Design synthesis and structure-activity relationship of 5-substituted (tetrahydronaphthalen-2yl)methyl with N-phenyl-N-(piperidin-2-yl)propionamide derivatives as opioid ligands.

PubMed

Deekonda, Srinivas; Rankin, David; Davis, Peg; Lai, Josephine; Vanderah, Todd W; Porecca, Frank; Hruby, Victor J

2016-01-15

Here, we report the design, synthesis and structure activity relationship of novel small molecule opioid ligands based on 5-amino substituted (tetrahydronaphthalen-2-yl)methyl moiety with N-phenyl-N-(piperidin-2-yl)propionamide derivatives. We synthesized various molecules including amino, amide and hydroxy substitution on the 5th position of the (tetrahydronaphthalen-2-yl)methyl moiety. In our further designs we replaced the (tetrahydronaphthalen-2-yl)methyl moiety with benzyl and phenethyl moiety. These N-phenyl-N-(piperidin-2-yl)propionamide analogues showed moderate to good binding affinities (850-4 nM) and were selective towards the μ opioid receptor over the δ opioid receptors. From the structure activity relationship studies, we found that a hydroxyl substitution at the 5th position of (tetrahydronapthalen-2yl)methyl group, ligands 19 and 20, showed excellent binding affinities 4 and 5 nM, respectively, and 1000 fold selectivity towards the μ opioid relative to the delta opioid receptor. The ligand 19 showed potent agonist activities 75±21 nM, and 190±42 nM in the GPI and MVD assays. Surprisingly the fluoro analogue 20 showed good agonist activities in MVD assays 170±42 nM, in contrast to its binding affinity results. Copyright © 2015 Elsevier Ltd. All rights reserved.

Synthesis, molecular structure and spectroscopic investigations of novel fluorinated spiro heterocycles.

PubMed

Islam, Mohammad Shahidul; Al-Majid, Abdullah Mohammed; Barakat, Assem; Soliman, Saied M; Ghabbour, Hazem A; Quah, Ching Kheng; Fun, Hoong-Kun

2015-05-07

This paper describes an efficient and regioselective method for the synthesis of novel fluorinated spiro-heterocycles in excellent yield by cascade [5+1] double Michael addition reactions. The compounds 7,11-bis(4-fluorophenyl)-2,4-dimethyl- 2,4-diazaspiro[5.5] undecane-1,3,5,9-tetraone (3a) and 2,4-dimethyl-7,11-bis (4-(trifluoromethyl)phenyl)-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone (3b) were characterized by single-crystal X-ray diffraction, FT-IR and NMR techniques. The optimized geometrical parameters, infrared vibrational frequencies and NMR chemical shifts of the studied compounds have also been calculated using the density functional theory (DFT) method, using Becke-3-Lee-Yang-Parr functional and the 6-311G(d,p) basis set. There is good agreement between the experimentally determined structural parameters, vibrational frequencies and NMR chemical shifts of the studied compounds and those predicted theoretically. The calculated natural atomic charges using NBO method showed higher polarity of 3a compared to 3b.The calculated electronic spectra are also discussed based on the TD-DFT calculations.

Bifunctional phenyl monophosphonic/sulfonic acid ion exchange resin and process for using the same

DOEpatents

Alexandratos, Spiro; Shelley, Christopher A.; Horwitz, E. Philip; Chiarizia, Renato

2001-01-01

A cross-linked water-insoluble ion exchange resin comprised of polymerized monomers having a phenyl ring is disclosed. A contemplated resin contains (i) polymerized phenyl ring-containing monomers having a phosphonic acid ligand linked to the phenyl ring, (ii) about 2 to about 5 millimoles per gram (mmol/g) of phosphorus as phosphonic acid ligands, and (iii) a sufficient amount of a sulfonic acid ligand such that the ratio of mmol/g of phosphonic acid to mmol/g sulfonic acid is up to 3:1. A process for removing polyvalent metal cations from aqueous solution, and a process for removing iron(III) cations from acidic copper(II) cation-containing solutions that utilize the contemplated resin or other resins are disclosed.

Bifunctional phenyl monophosphonic/sulfonic acid ion exchange resin and process for using the same

DOEpatents

Alexandratos, Spiro; Shelley, Christopher A.; Horwitz, E. Philip; Chiarizia, Renato; Gula, Michael J.; Xue, Sui; Harvey, James T.

2002-01-01

A cross-linked water-insoluble ion exchange resin comprised of polymerized monomers having a phenyl ring is disclosed. A contemplated resin contains (i) polymerized phenyl ring-containing monomers having a phosphonic acid ligand linked to the phenyl ring, (ii) about 2 to about 5 millimoles per gram (mmol/g) of phosphorus as phosphonic acid ligands, and (iii) a sufficient amount of a sulfonic acid ligand such that the ratio of mmol/g of phosphonic acid to mmol/g sulfonic acid is up to 3:1. A process for removing polyvalent metal cations from aqueous solution, and a process for removing iron(III) cations from acidic copper(II) cation-containing solutions that utilize the contemplated resin or other resins are disclosed.

Control of intramolecular π-π stacking interaction in cationic iridium complexes via fluorination of pendant phenyl rings.

PubMed

He, Lei; Ma, Dongxin; Duan, Lian; Wei, Yongge; Qiao, Juan; Zhang, Deqiang; Dong, Guifang; Wang, Liduo; Qiu, Yong

2012-04-16

Intramolecular π-π stacking interaction in one kind of phosphorescent cationic iridium complexes has been controlled through fluorination of the pendant phenyl rings on the ancillary ligands. Two blue-green-emitting cationic iridium complexes, [Ir(ppy)(2)(F2phpzpy)]PF(6) (2) and [Ir(ppy)(2)(F5phpzpy)]PF(6) (3), with the pendant phenyl rings on the ancillary ligands substituted with two and five fluorine atoms, respectively, have been synthesized and compared to the parent complex, [Ir(ppy)(2)(phpzpy)]PF(6) (1). Here Hppy is 2-phenylpyridine, F2phpzpy is 2-(1-(3,5-difluorophenyl)-1H-pyrazol-3-yl)pyridine, F5phpzpy is 2-(1-pentafluorophenyl-1H-pyrazol-3-yl)-pyridine, and phpzpy is 2-(1-phenyl-1H-pyrazol-3-yl)pyridine. Single crystal structures reveal that the pendant phenyl rings on the ancillary ligands stack to the phenyl rings of the ppy ligands, with dihedral angles of 21°, 18°, and 5.0° between least-squares planes for complexes 1, 2, and 3, respectively, and centroid-centroid distances of 3.75, 3.65, and 3.52 Å for complexes 1, 2, and 3, respectively, indicating progressively reinforced intramolecular π-π stacking interactions from complexes 1 to 2 and 3. Compared to complex 1, complex 3 with a significantly reinforced intramolecular face-to-face π-π stacking interaction exhibits a significantly enhanced (by 1 order of magnitude) photoluminescent efficiency in solution. Theoretical calculations reveal that in complex 3 it is unfavorable in energy for the pentafluorophenyl ring to swing by a large degree and the intramolecular π-π stacking interaction remains on the lowest triplet state. © 2012 American Chemical Society

Pincer phosphine complexes of ruthenium: formation of Ru(P-O-P)(PPh3)HCl (P-O-P = xantphos, DPEphos, (Ph2PCH2CH2)2O) and Ru(dppf)(PPh3)HCl and characterization of cationic dioxygen, dihydrogen, dinitrogen, and arene coordinated phosphine products.

PubMed

Ledger, Araminta E W; Moreno, Aitor; Ellul, Charles E; Mahon, Mary F; Pregosin, Paul S; Whittlesey, Michael K; Williams, Jonathan M J

2010-08-16

Treatment of Ru(PPh(3))(3)HCl with the pincer phosphines 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (xantphos), bis(2-diphenylphosphinophenyl)ether (DPEphos), or (Ph(2)PCH(2)CH(2))(2)O affords Ru(P-O-P)(PPh(3))HCl (xantphos, 1a; DPEphos, 1b; (Ph(2)PCH(2)CH(2))(2)O, 1c). The X-ray crystal structures of 1a-c show that all three P-O-P ligands coordinate in a tridentate manner through phosphorus and oxygen. Abstraction of the chloride ligand from 1a-c by NaBAr(4)(F) (BAr(4)(F) = B(3,5-C(6)H(3)(CF(3))(2))(4)) gives the cationic aqua complexes [Ru(P-O-P)(PPh(3))(H(2)O)H]BAr(4)(F) (3a-c). Removal of chloride from 1a by AgOTf yields Ru(xantphos)(PPh(3))H(OTf) (2a), which reacts with water to form [Ru(xantphos)(PPh(3))(H(2)O)H](OTf). The aqua complexes 3a-b react with O(2) to generate [Ru(xantphos)(PPh(3))(eta(2)-O(2))H]BAr(4)(F) (5a) and [Ru(DPEphos)(PPh(3))(eta(2)-O(2))H]BAr(4)(F) (5b). Addition of H(2) or N(2) to 3a-c yields the thermally unstable dihydrogen and dinitrogen species [Ru(P-O-P)(PPh(3))(eta(2)-H(2))H]BAr(4)(F) (6a-c) and [Ru(P-O-P)(PPh(3))(N(2))H]BAr(4)(F) (7a-c), which have been characterized by multinuclear NMR spectroscopy at low temperature. Ru(PPh(3))(3)HCl reacts with 1,1'-bis(diphenylphosphino)ferrocene (dppf) to give the 16-electron complex Ru(dppf)(PPh(3))HCl (1d), which upon treatment with NaBAr(4)(F), affords [Ru(dppf){(eta(6)-C(6)H(5))PPh(2)}H]BAr(4)(F) (8), in which the PPh(3) ligand binds eta(6) through one of the PPh(3) phenyl rings. Reaction of 8 with CO or PMe(3) at elevated temperatures yields the 18-electron products [Ru(dppf)(PPh(3))(CO)(2)H]BAr(F)(4) (9) and [Ru(PMe(3))(5)H]BAr(4)(F) (10).

Electrically conductive alternating copolymers

DOEpatents

Aldissi, M.; Jorgensen, B.S.

1987-08-31

Polymers which are soluble in common organic solvents and are electrically conductive, but which also may be synthesized in such a manner that they become nonconductive. Negative ions from the electrolyte used in the electrochemical synthesis of a polymer are incorporated into the polymer during the synthesis and serve as a dopant. A further electrochemical step may be utilized to cause the polymer to be conductive. The monomer repeat unit is comprised of two rings, a pyrrole molecule joined to a thienyl group, or a furyl group, or a phenyl group. The individual groups of the polymers are arranged in an alternating manner. For example, the backbone arrangement of poly(furylpyrrole) is -furan-pyrrole-furan-pyrrole- furan-pyrrole. An alkyl group or phenyl group may be substituted for either or both of the hydrogen atoms of the pyrrole ring.

Spectroscopic (FT-IR, FT-Raman and UV) investigation, NLO, NBO, molecular orbital and MESP analysis of 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid

NASA Astrophysics Data System (ADS)

Govindasamy, P.; Gunasekaran, S.

2015-02-01

In this work, FT-IR and FT-Raman spectra of 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid (abbreviated as 2DCPAPAA) have been reported in the regions 4000-450 cm-1 and 4000-50 cm-1, respectively. The molecular structure, geometry optimization, intensities, vibrational frequencies were obtained by the ab initio and DFT levels of theory B3LYP with 6-311++G(d,p) standard basis set and a different scaling of the calculated wave numbers. The complete vibrational assignments were performed on the basis of the potential energy distribution (PED) of the vibrational modes calculated using vibrational energy distribution analysis (VEDA 4) program. The harmonic frequencies were calculated and the scaled values were compared with experimental FT-IR and FT-Raman data. The observed and the calculated frequencies are found to be in good agreement. Stability of the molecule arising from hyper conjugative interactions, charge delocalization has been analyzed using natural bond orbital (NBO) analysis. The thermodynamic properties of the title compound at different temperature reveal the correlations between standard heat capacities (C) standard entropies (S) standard enthalpy changes (ΔH). The important non-linear optical properties such as electric dipole momentum, polarizability and first hyperpolarizability of 2DCPAPAA have been computed using B3LYP/6-311++G(d,p) quantum chemical calculations. The Natural charges, HOMO, LUMO, chemical hardness (η), chemical potential (μ), Electro negativity (χ) and electrophilicity values (ω) are calculated and reported. The oscillator's strength, wave length, and energy calculated by TD-DFT and 2DCPAPAA is approach complement with the experimental findings. The molecular electrostatic potential (MESP) surfaces of the molecule were constructed.

2-(4-Meth-oxy-phen-yl)-1-pentyl-4,5-di-phenyl-1H-imidazole.

PubMed

Simpson, Jim; Mohamed, Shaaban K; Marzouk, Adel A; Talybov, Avtandil H; Abdelhamid, Antar A

2013-01-01

The title compound, C27H28N2O, is a lophine (2,4,5-triphenyl-1H-imidazole) derivative with an n-pentyl chain on the amine N atom and a 4-meth-oxy substituent on the benzene ring. The two phenyl and meth-oxy-benzene rings are inclined to the imidazole ring at angles of 25.32 (7), 76.79 (5) and 35.42 (7)°, respectively, while the meth-oxy substituent lies close to the plane of its benzene ring, with a maximum deviation of 0.126 (3) Å for the meth-oxy C atom. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R2(2)(22) loops. These dimers are stacked along the a-axis direction.

Discovery of 3-(3-(4-(1-Aminocyclobutyl)phenyl)-5-phenyl-3 H -imidazo[4,5- b ]pyridin-2-yl)pyridin-2-amine (ARQ 092): An Orally Bioavailable, Selective, and Potent Allosteric AKT Inhibitor

DOE Office of Scientific and Technical Information (OSTI.GOV)

Lapierre, Jean-Marc; Eathiraj, Sudharshan; Vensel, David

The work in this paper describes the optimization of the 3-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine chemical series as potent, selective allosteric inhibitors of AKT kinases, leading to the discovery of ARQ 092 (21a). The cocrystal structure of compound 21a bound to full-length AKT1 confirmed the allosteric mode of inhibition of this chemical class and the role of the cyclobutylamine moiety. Compound 21a demonstrated high enzymatic potency against AKT1, AKT2, and AKT3, as well as potent cellular inhibition of AKT activation and the phosphorylation of the downstream target PRAS40. Compound 21a also served as a potent inhibitor of the AKT1-E17K mutant protein and inhibited tumormore » growth in a human xenograft mouse model of endometrial adenocarcinoma.« less

Separation of americium from europium using 3,3'-dimethoxy-phenyl-bis-1,2,4-triazinyl-2,6-pyridine

DOE PAGES

Hill, Talon G.; Chin, Ai Lin; Tai, Serene; ...

2017-03-22

Development of liquid-liquid separation processes for the effective removal of the minor actinide Am(III) from used nuclear fuel using ligand-based strategies continues to be an area of significant research focus. The current investigation demonstrates the efficacy of a nitrogen-based bis-triazinyl pyridine (BTP) derivative to selectively extract Am(III) from nitric acid solutions containing light lanthanides. The performance of 3,3’-dimethoxy-phenyl-bis-1,2,4-triazinyl-2,6- pyridine (MOB-BTP) was compared to that of a camphor substituted BTP (CA-BTP). The results of this investigation demonstrate the novel 3,3’-methoxy-BTP extractant dissolved in a polar diluent was a more efficient extractant for Am(III) at a lower concentration than CA-BTP under comparablemore » conditions.« less

Separation of americium from europium using 3,3'-dimethoxy-phenyl-bis-1,2,4-triazinyl-2,6-pyridine

DOE Office of Scientific and Technical Information (OSTI.GOV)

Hill, Talon G.; Chin, Ai Lin; Tai, Serene

Development of liquid-liquid separation processes for the effective removal of the minor actinide Am(III) from used nuclear fuel using ligand-based strategies continues to be an area of significant research focus. The current investigation demonstrates the efficacy of a nitrogen-based bis-triazinyl pyridine (BTP) derivative to selectively extract Am(III) from nitric acid solutions containing light lanthanides. The performance of 3,3’-dimethoxy-phenyl-bis-1,2,4-triazinyl-2,6- pyridine (MOB-BTP) was compared to that of a camphor substituted BTP (CA-BTP). The results of this investigation demonstrate the novel 3,3’-methoxy-BTP extractant dissolved in a polar diluent was a more efficient extractant for Am(III) at a lower concentration than CA-BTP under comparablemore » conditions.« less

N-[5-(Di­phenyl­phosphorylmeth­yl)-4-(4-fluoro­phen­yl)-6-iso­propyl­pyrimi­din-2-yl]-N-methyl­methane­sulfonamide

PubMed Central

Wu, Ya-Ming

2013-01-01

In the title compound, C28H29FN3O3PS, the pyrimidine ring is oriented at a dihedral angle of 50.9 (2)° with respect to the floro­benzene ring, while the two phenyl rings bonding to the same P atom are twisted with respect to each other, making a dihedral angle of 62.2 (2)°. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯F hydrogen bonds into a three-dimensional supra­molecular architecture. PMID:24454107

The physiological disposition of the uricosuric-saluretic agent (6,7-dichloro-2-methyl-1-oxo-2-phenyl-5-indanyloxy)acetic acid (MK-196) in the rat, dog, and monkey.

PubMed

Zacchei, A G; Wishousky, T I

1976-01-01

The physiological disposition of a new saluretic-uricosuric agent, (6,7-dichloro-2-methyl-1-oxo-2-phenyl-5-indanyloxy)acetic acid (MK-196), was studied in the rat, dog, and monkey. MK-196 was well absorbed and showed minimal metabolism in these species. Peak plasma levels of radioactivity and drug occurred 0.5-2 hr after oral administration at a dose of 2.5 mg/kg. Essentially all of the radioactivity present in the plasma during the first day was intact MK-196. Following a single dose, a long terminal half-life for plasma radioactivity was observed in the dog (approximately 68 hr) and monkey (approximately 105 hr). The chronic administration of MK-196 to dogs resulted in a dose-related plasma profile and showed no tendency to increase or decrease with dosing. However, upon repeated drug administration to monkeys, the plasma levels of drug increased and then decreased, possibly due to hypochloremia and secondary metabolic alkalosis. Fecal excretion was the predominant route of tracer elimination in the dog (approximately 80%) and rat (approximately 94%), whereas the monkey eliminated the majority of the dose (approximately 60%) via the urine. Minimal metabolism was noted in the three lower species; most of the urinary, plasma, and fecal radioactivity was accounted for as intact drug and its glucuronide conjugate. Three minor metabolites, which were present in dog bile, plasma, and urine, were characterized as: (l,7-dichloro-1alpha-hydroxy-2-methyl-2-phenyl-5-indanyloxy)acetic acid, I; (6,7-dichloro-2-(4-hydroxyphenyl)-2-methyl-2-oxo-5-indanyloxy)acetic acid, II; and 2-methyl-2-phenyl-5-hydroxy-6,7-dichloro-1-indanone, III. The monkey urine and plasma also contained small amounts of II.

Mechanism of permeability-enhancing effect of EDTA and boric acid on the corneal penetration of 4-[1-hydroxy-1-methylethyl]-2-propyl-1-[4-[2-[tetrazole-5-yl]phenyl]phenyl] methylimidazole-5-carboxylic acid monohydrate (CS-088).

PubMed

Kikuchi, Takayuki; Suzuki, Masahiko; Kusai, Akira; Iseki, Ken; Sasaki, Hitoshi; Nakashima, Kenichiro

2005-08-11

This study was conducted to clarify the penetration properties of 4-[1-hydroxy-1-methylethyl]-2-propyl-1-[4-[2-[tetrazole-5-yl]phenyl]phenyl]methylimidazole-5-carboxylic acid monohydrate (CS-088), an ophthalmic agent, and the mechanism of the permeability-enhancing effect of EDTA and boric acid (EDTA/boric acid) on the corneal penetration of CS-088. In the absence of additives, corneal permeability decreased with increasing concentration of CS-088 as CS-088 monomers self-associate to form dimers. Presence of EDTA/boric acid caused no significant changes in the physicochemical properties of CS-088, the apparent partition coefficient or the mean particle size of CS-088. EDTA/boric acid induced only a slight change in the zeta potential of liposomes used as a model of the biological membrane. On the other hand, EDTA/boric acid significantly increased membrane fluidity of liposomes, whereas other buffering agents tested did not. This effect was synergistic and concentration-dependent for both EDTA and boric acid as was observed in in vitro corneal penetration of CS-088. In accordance with the result, the rate of CS-088 permeation into the liposomes significantly increased by the addition of EDTA/boric acid. Therefore, it was demonstrated that EDTA/boric acid promotes corneal penetration of CS-088 through the transcellular pathway by increasing membrane fluidity. Conversely, other buffering agents decreased corneal permeability of CS-088 by inducing further self-association of CS-088 aggregates.

Crystal structure of tricarbon­yl(μ-di­phenyl­phosphido-κ2 P:P)(methyl­diphenyl­silyl-κSi)bis(tri­phenyl­phosphane-κP)iron(II)platinum(0)(Fe—Pt)

PubMed Central

Mohamed, Ahmed Said; Jourdain, Isabelle; Knorr, Michael; Rousselin, Yoann; Kubicki, Marek M.

2015-01-01

The title compound, [FePt(C12H10P)(C13H13Si)(C18H15P)2(CO)3]·0.5CH2Cl2, represents an example of a phosphido-bridged heterobimetallic silyl complex; these are inter­esting precursors for the coordination and activation of small unsaturated organic mol­ecules. The μ2-PPh2 ligand spans the iron and platinum atoms, which are connected via a metal–metal bond of 2.7738 (4) Å. In contrast to most other complexes of the [(OC)3Fe(SiR 3)(μ-PR 2)PtL 2] family, where the iron-bound SiR 3 group is trans-arranged with respect to the μ2-PPh2 ligand, the SiPh2Me ligand is roughly collinear with the Fe–Pt vector [Si—Fe—Pt = 169.07 (3)°]. PMID:25878830

1-{(E)-[(2E)-3-(4-Meth-oxy-phen-yl)-1-phenyl-prop-2-en-1-yl-idene]amino}-3-phenyl-urea: crystal structure and Hirshfeld surface analysis.

PubMed

Tan, Ming Yueh; Crouse, Karen A; Ravoof, Thahira B S A; Jotani, Mukesh M; Tiekink, Edward R T

2017-11-01

The title compound, C 23 H 21 N 3 O 2 , is constructed about an almost planar disubstituted amino-urea residue (r.m.s. deviation = 0.0201 Å), which features an intra-molecular amine-N-H⋯N(imine) hydrogen bond. In the 'all- trans ' chain connecting this to the terminal meth-oxy-benzene residue, the conformation about each of the imine and ethyl-ene double bonds is E . In the crystal, amide-N-H⋯O(carbon-yl) hydrogen bonds connect centrosymmetrically related mol-ecules into dimeric aggregates, which also incorporate ethyl-ene-C-H⋯O(amide) inter-actions. The dimers are linked by amine-phenyl-C-H⋯π(imine-phen-yl) and meth-oxy-benzene-C-H⋯π(amine-phen-yl) inter-actions to generate a three-dimensional network. The importance of C-H⋯π inter-actions in the mol-ecular packing is reflected in the relatively high contributions made by C⋯H/H⋯C contacts to the Hirshfeld surface, i.e . 31.6%.

Enantioconvergent hydrolysis of racemic styrene oxide at high concentration by a pair of novel epoxide hydrolases into (R)-phenyl-1,2-ethanediol.

PubMed

Wang, Rui; Hu, Die; Zong, Xuncheng; Li, Jinping; Ding, Lei; Wu, Minchen; Li, Jianfang

2017-12-01

To prepare (R)-phenyl-1,2-ethanediol ((R)-PED) with high enantiomeric excess (ee p ) and yield from racemic styrene oxide (rac-SO) at high concentration by bi-enzymatic catalysis. The bi-enzymatic catalysis was designed for enantioconvergent hydrolysis of rac-SO by a pair of novel epoxide hydrolases (EHs), a Vigna radiata EH3 (VrEH3) and a variant (AuEH2 A250I ) of Aspergillus usamii EH2. The simultaneous addition mode of VrEH3 and AuEH2 A250I , exhibiting the highest average turnover frequency (aTOF) of 0.12 g h -1 g -1 , was selected, by which rac-SO (10 mM) was converted into (R)-PED with 92.6% ee p and 96.3% yield. Under the optimized reaction conditions: dry weight ratio 14:1 of VrEH3-expressing E. coli/vreh3 to AuEH2 A250I -expressing E. coli/Aueh2 A250I and reaction at 20 °C, rac-SO (10 mM) was completely hydrolyzed in 2.3 h, affording (R)-PED with 98% ee p . At the weight ratio 0.8:1 of rac-SO to two mixed dry cells, (R)-PED with 97.4% ee p and 98.7% yield was produced from 200 mM (24 mg/ml) rac-SO in 10.5 h. Enantioconvergent hydrolysis of rac-SO at high concentration catalyzed by both VrEH3 and AuEH2 A250I is an effective method for preparing (R)-PED with high ee p and yield.

2-(Benzothiazol-2-yl)-phenyl-β-d-galactopyranoside derivatives as fluorescent pigment dyeing substrates and their application for the assay of β-d-galactosidase activities.

PubMed

Otsubo, Tadamune; Minami, Akira; Fujii, Haruna; Taguchi, Risa; Takahashi, Tadanobu; Suzuki, Takashi; Teraoka, Fumiteru; Ikeda, Kiyoshi

2013-04-01

2-(Benzothiazol-2-yl)-phenyl-β-d-galactopyranoside derivatives were synthesized as novel artificial fluorescent pigment dyeing substrates for β-d-galactosidase. The substrates, which exhibited non-fluorescence or weak fluorescence in solution phase, were smoothly hydrolyzed by β-d-galactosidase from Aspergillus oryzae and yielded a water-insoluble strong fluorescent pigment. The difference of fluorescent intensity exhibited a linear relationship with the amount of enzyme. Copyright © 2013 Elsevier Ltd. All rights reserved.

(Z)-3-Methyl-4-[1-(4-methyl­anilino)propyl­idene]-1-phenyl-1H-pyrazol-5(4H)-one

PubMed Central

Sharma, Naresh; Vyas, Komal M.; Jadeja, R. N.; Kant, Rajni; Gupta, Vivek K.

2013-01-01

In the title mol­ecule, C20H21N3O, the central pyrazole ring forms dihedral angles of 4.75 (9) and 49.11 (9)°, respectively, with the phenyl and methyl-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 51.76 (8)°. The amino group and carbonyl O atom are involved in an intra­molecular N—H⋯O hydrogen bond. In the crystal, π–π inter­actions are observed between benzene rings [centroid–centroid seperation = 3.892 (2) Å] and pyrazole rings [centroid–centroid seperation = 3.626 (2) Å], forming chains along [111]. The H atoms of the methyl group on the p-tolyl substituent were refined as disordered over two sets of sites in a 0.60 (4):0.40 (4) ratio. PMID:24109353

Effects of counterions of colorful sandwich-type zinc(II) 4‧-phenyl-terpyridine compounds on photoluminescent and thermal properties

NASA Astrophysics Data System (ADS)

Zhang, Yongqiang; Zhou, Peng; Liang, Baohuan; Huang, Ling; Zhou, Yanling; Ma, Zhen

2017-10-01

Reactions between 4‧-phenyl-terpyridine (L) and several Zn(II) salts (p-toluenesulfonate, nitrate, trifluoromethane sulfonate or hexafluoroantimonate) led to the formation of the complexes [ZnL2](p-OSO2PhCH3)2 (1), [ZnL2](NO3)2 (2), [ZnL2](SO3CF3)2 (3) and [ZnL2](SbF6)2 (4), which were characterized by IR, 1H NMR, elemental analysis, UV-vis spectroscopies and single crystal X-ray diffraction, along with their TG-DTA thermal and photoluminescent properties. The four compounds show mononuclear Zn(II) structures with hexacoordinated, irregular ZnN6 octahedron geometries. Their colours and photo-luminescent properties have changed regularly depending on the counterions of the compounds.

Cyclo-oxygenase-2 contributes to constitutive prostanoid production in rat kidney and brain

PubMed Central

2005-01-01

Cyclo-oxygenases (COXs) catalyse the synthesis of PGH2 (prostaglandin H2), which serves as the common substrate for the production of PGE2, PGD2, PGF2α, prostacyclin (or PGI2) and TXs (thromboxanes). While COX-1 is the major isoform responsible for prostanoid synthesis in healthy tissues, little information is available on the contribution of constitutive COX-2 to the various prostanoid synthetic pathways under non-inflammatory conditions. To evaluate further the role of COX-2 in prostanoid biosynthesis, rats were acutely treated with the selective COX-1 inhibitor SC-560 [5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-trifluoromethylpyrazole] or the selective COX-2 inhibitors MF tricyclic [3-(3,4-difluorophenyl)-4-(4-(methylsulphonyl)phenyl)-2-(5H)-furanone] and DFU [5,5-dimethyl-3-(3-fluorophenyl)-4-(4-methylsulphonyl)phenyl-2-(5H)-furanone]. Selected tissues were then processed for a complete analysis of their prostanoid content by liquid chromatography MS. Whereas the treatment with SC-560 caused a 60–70% inhibition in the total prostanoid content of most tissues examined, a significant decrease (35–50%) in total prostanoid content following selective COX-2 inhibition was solely detected for kidney and brain tissues. Analysis of the individual prostanoids reveals significant inhibition of 6-oxo-PGF1α, PGE2, PGD2, PGF2α and TXB2 in the kidney and inhibition of all these prostanoids with the exception of PGD2 in the forebrain. These results demonstrate that constitutively expressed COX-2 contributes to the production of prostanoids in kidney and brain for each of the PGE2, PGI2 and TXB2 pathways under non-inflammatory conditions. Approaches to modulate inflammation through specific inhibition of terminal synthases, such as mPGES-1 (microsomal PGE2 synthase-1), thus have the potential to differ from COX-2 inhibitors and non-selective non-steroidal anti-inflammatory drugs with regard to effects on constitutive prostanoid synthesis and on renal function. PMID

Spectroscopic (FT-IR, FT-Raman and UV) investigation, NLO, NBO, molecular orbital and MESP analysis of 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid.

PubMed

Govindasamy, P; Gunasekaran, S

2015-02-05

In this work, FT-IR and FT-Raman spectra of 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid (abbreviated as 2DCPAPAA) have been reported in the regions 4000-450cm(-1) and 4000-50cm(-1), respectively. The molecular structure, geometry optimization, intensities, vibrational frequencies were obtained by the ab initio and DFT levels of theory B3LYP with 6-311++G(d,p) standard basis set and a different scaling of the calculated wave numbers. The complete vibrational assignments were performed on the basis of the potential energy distribution (PED) of the vibrational modes calculated using vibrational energy distribution analysis (VEDA 4) program. The harmonic frequencies were calculated and the scaled values were compared with experimental FT-IR and FT-Raman data. The observed and the calculated frequencies are found to be in good agreement. Stability of the molecule arising from hyper conjugative interactions, charge delocalization has been analyzed using natural bond orbital (NBO) analysis. The thermodynamic properties of the title compound at different temperature reveal the correlations between standard heat capacities (C) standard entropies (S) standard enthalpy changes (ΔH). The important non-linear optical properties such as electric dipole momentum, polarizability and first hyperpolarizability of 2DCPAPAA have been computed using B3LYP/6-311++G(d,p) quantum chemical calculations. The Natural charges, HOMO, LUMO, chemical hardness (η), chemical potential (μ), Electro negativity (χ) and electrophilicity values (ω) are calculated and reported. The oscillator's strength, wave length, and energy calculated by TD-DFT and 2DCPAPAA is approach complement with the experimental findings. The molecular electrostatic potential (MESP) surfaces of the molecule were constructed. Copyright © 2014 Elsevier B.V. All rights reserved.

Synthesis and biological evaluation of 2-fluoro and 3-trifluoromethyl-phenyl-piperazinylalkyl derivatives of 1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione as potential antidepressant agents.

PubMed

Zagórska, Agnieszka; Bucki, Adam; Kołaczkowski, Marcin; Siwek, Agata; Głuch-Lutwin, Monika; Starowicz, Gabriela; Kazek, Grzegorz; Partyka, Anna; Wesołowska, Anna; Słoczyńska, Karolina; Pękala, Elżbieta; Pawłowski, Maciej

2016-01-01

A series of 2-fluoro and 3-trifluoromethylphenylpiperazinylalkyl derivatives of 1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione (4-21) were synthesized and evaluated for their serotonin (5-HT 1A /5-HT 7 ) receptor affinity and phosphodiesterase (PDE4B and PDE10A) inhibitor activity. The study enabled the identification of potent 5-HT 1A , 5-HT 7 and mixed 5-HT 1A /5-HT 7 receptor ligands with weak inhibitory potencies for PDE4B and PDE10A. The tests have been completed with the determination of lipophilicity and metabolic stability using micellar electrokinetic chromatography (MEKC) system and human liver microsomes (HLM) model. In preliminary pharmacological in vivo studies, selected compound 8-(5-(4-(2-fluorophenyl)piperazin-1-yl)pentyl)-1,3,7-trimethyl-1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione (9) behaved as a potential antidepressant in forced swim test (FST) in mice. Moreover, potency of antianxiety effects evoked by 9 (2.5 mg/kg) is greater than that of the reference anxiolytic drug, diazepam. Molecular modeling revealed that fluorinated arylpiperazinylalkyl derivatives of 1H-imidazo[2,1-f]purine-2,4(3H,8H)-dione have major significance for the provision of lead compounds for antidepressant and/or anxiolytic application.

New phenyl-ethanediols from the culture broth of Boletus edulis.

PubMed

Yang, Wan-Qiu; Qin, Xiang-Dong; Shao, Hong-Jun; Fang, Li-Zhen; Wang, Fei; Ding, Zhi-Hui; Dong, Ze-Jun; Liu, Ji-Kai

2007-04-01

A new phenyl-ethanediol, (1S)-(4-acetylphenyl)-1, 2-ethanediol (1), and a new natural product, (1S)-(3-ethenylphenyl)-1, 2-ethanediol (2), were isolated from the culture broth of the basidiomycete Boletus edulis together with three related known compounds, 1-(4-ethylphenyl)-1, 2-ethanediol (3), 1-(3-ethylphenyl)-1, 2-ethanediol (4) and 1-(3-formylphenyl)-ethanone (5). Their structures were elucidated by spectroscopic methods including extensive 2D-NMR techniques.

Discovery of novel EGFR tyrosine kinase inhibitors by structure-based virtual screening.

PubMed

Li, Siyuan; Sun, Xianqiang; Zhao, Hongli; Tang, Yun; Lan, Minbo

2012-06-15

By using of structure-based virtual screening, 13 novel epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors were discovered from 197,116 compounds in the SPECS database here. Among them, 8 compounds significantly inhibited EGFR kinase activity with IC(50) values lower than 10 μM. 3-{[1-(3-Chloro-4-fluorophenyl)-3,5-dioxo-4-pyrazolidinylidene]methyl}phenyl 2-thiophenecarboxylate (13), particularly, was the most potent inhibitor possessing the IC(50) value of 3.5 μM. The docking studies also provide some useful information that the docking models of the 13 compounds are beneficial to find a new path for designing novel EGFR inhibitors. Copyright © 2012 Elsevier Ltd. All rights reserved.

Synthesis, crystal structure, characterization and antifungal activity of 3,4-diaryl-1H-Pyrazoles derivatives

NASA Astrophysics Data System (ADS)

Zhang, Jin; Tan, Da-Jin; Wang, Tao; Jing, Si-Si; Kang, Yang; Zhang, Zun-Ting

2017-12-01

A series of 3,4-diaryl-1H-pyrazoles derivatives were designed and synthesized by the reaction of 3-heteroarylchromones and 3-phenylchromones with hydrazine hydrate in good yields. All of those compounds were characterized by 1H NMR, 13C NMR, IR, and HRMS. Moreover, 3-(2,4-dihydroxyphenyl)-4-(4-hydroxyphenyl)-1H-pyrazole and 3-(2,4-dihydroxy phenyl)-4-(4-methoxyphenyl)-1H-pyrazole were further conformed by the single crystal X-ray diffraction. In addition, the antifungal activity against five phytopathogenic fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani and Fusarium solani) of 3,4-diaryl-1H-pyrazoles were evaluated. 3-(2-Hydroxy-4-isopropoxyphenyl)-4-phenyl-1H-pyrazole was more better and broader inhibitory effect on Cytospora sp., C. gloeosporioides, A. solani and Fusarium solani with IC50 values of 26.96, 28.84, 16.77 and 22.10 μg/mL, respectively. 4-(4-Fluorophenyl)-3-(2-hydroxy-4-methoxyphenyl)-1H-pyrazole exhibited fairly effective antifungal activity against Cytospora sp., C. gloeosporioides and A. solani with IC50 values of 11.91, 14.92 and 16.98 μg/mL, respectively.

Influence of 6-phenyl-3(2H)-pyridazinone and 3-chloro-6-phenylpyrazine on mild steel corrosion in 0.5 M HCl medium: Experimental and theoretical studies

NASA Astrophysics Data System (ADS)

Olasunkanmi, Lukman O.; Sebona, Mabina Frans; Ebenso, Eno E.

2017-12-01

Two pyridazine derivatives, namely, 6-phenyl-3(2H)-pyridazinone (P1) and 3-chloro-6-phenylpyrazine (P2) were investigated for their influence on mild steel corrosion in 0.5 M HCl, using Tafel polarization, electrochemical impedance spectroscopy (EIS), surface morphology, FTIR and UV-vis techniques. Quantum chemical calculations were also conducted to corroborate experimental findings. P1 was found to accelerate corrosion at low concentrations but exhibits inhibitive action at higher concentrations, attaining 61% inhibition efficiency at 1.25 mM. The inhibitive action of P2 increases with increasing concentration from 88% at 0.1 mM to 96% at 1.25 mM as deduced from EIS measurements. Both compounds are mixed type inhibitors. P2 seems to display chiefly anodic inhibitive effects. The adsorption of P2 on mild steel surface obeys the Langmuir adsorption isotherm and involved competitive physisorption and chemisorption mechanisms. Scanning electron microscopy analyses of steel surfaces in acid-inhibitor solutions showed that both compounds protect mild steel surface effectively at 1.25 mM. FTIR and UV-vis spectroscopic analyses revealed that Nsbnd H, Cdbnd O, and Csbnd N functional groups of the pyridazine derivatives are actively involved in adsorption of the molecules onto steel surface. Quantum chemical parameters showed that the higher inhibition efficiency of P2 compared to P1 might be related to better electron acceptance ability of P2.

Structure determination of two structural analogs, named 3-[1-(2-fluoro-4-biphenyl)ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C23H16F2N4S) and 3-[1-(2-fluoro-4-biphenyl)ethyl]-6-(4-chlorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C23H16ClFN4S) by synchrotron X-ray powder diffraction

DOE Office of Scientific and Technical Information (OSTI.GOV)

Gündoğdu, Gülsüm; Aytaç, Sevim Peri; Müller, Melanie

Two novel compounds, 3-[1-(2-fluoro-4-biphenyl)ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C 23H 16F 2N 4S) (1) and 3-[1-(2-fluoro-4-biphenyl)ethyl]-6-(4-chlorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C 23H 16ClFN 4S) (2), have been designed and synthesized as cytotoxic agents. The compounds were characterized by infrared, proton nuclear magnetic resonance, mass spectral data, elemental analysis and X-ray powder diffraction. The present study comprises spectral data and crystal structures of these novel compounds determined from synchrotron X-ray powder diffraction data. The structure solutions were obtained by simulated annealing. The final structures were achieved by Rietveld refinement using soft restraints for all bond lengths, bond angles, and planar groups. Both compounds crystallize in space groupmore » $$P\\bar 1$$,Z= 2, with the unit-cell parametersa= 6.37433(9),b= 11.3641(2),c= 14.09115(19) Å,α= 80.1740(8)°,β= 85.1164(8)°,γ= 80.9831(10)°,V= 991.55(3) Å 3of compound (1) anda= 6.53736(6),b= 11.55725(15),c= 14.01373(13) Å,α= 80.3323(7)°,β= 84.8939(6)°,γ= 79.3954(8)°,V= 1024.08(2) Å 3of compound (2). Structural analyses reveal that the title compounds are isostructural.« less

The synthesis and biological evaluation of new DNA-directed alkylating agents, phenyl N-mustard-4-anilinoquinoline conjugates containing a urea linker.

PubMed

Marvania, Bhavin; Kakadiya, Rajesh; Christian, Wilson; Chen, Tai-Lin; Wu, Ming-Hsi; Suman, Sharda; Tala, Kiran; Lee, Te-Chang; Shah, Anamik; Su, Tsann-Long

2014-08-18

We synthesized a series of phenyl N-mustard-4-anilinoquinoline conjugates to study their antitumorigenic effects. These agents were prepared by the condensation of 4-[N,N-bis(2-chloroethyl)amino]phenyl isocyanate with 6-amino-4-methylamino or 4-anilinoquinolines. The structure-activity relationship (SAR) studies revealed that the C2-methylquinoline derivatives (18a-o) were generally more cytotoxic than the C2-phenylquinoline conjugates (23a-d) in inhibiting the cell growth of various human tumor cell lines in vitro. However, the methylamino or aniline substituents at C4 of quinoline did not influence the cytotoxic effects. The title conjugates were capable of inducing DNA cross-linking and promoting cell-cycle arrest at the G2/M phase. This study demonstrates that phenyl N-mustard-4-anilinoquinoline conjugates are generally more potent than phenyl N-mustard-4-anilinoquinazoline conjugates against the cell growth of various tumor cell-lines. Copyright © 2014 Elsevier Masson SAS. All rights reserved.

Pharmacological characterization of P2X7 receptors in rat peritoneal cells.

PubMed

Chen, Y-W; Donnelly-Roberts, D L; Namovic, M T; Gintant, G A; Cox, B F; Jarvis, M F; Harris, R R

2005-03-01

P2X(7) receptor activation by ATP results in the release of IL-1beta and IL-18. Prolonged stimulation can lead to pore formation and cell death. In this study we pharmacologically characterized P2X(7) receptors on rat peritoneal cells (RPC) and on 1321N1 cells transfected with rat P2X(7) receptor (1321rP2X(7)-11). RPC were isolated from rats by lavage. P2X(7) agonist induced pore formation in RPC was measured by EtBr uptake. P2X(7)-stimulated pore formation and Ca(++) influx in 1321rP2X(7)-11 cells were measured by a fluorometric imaging plate reader. The effects of pyridoxal phosphate-6-azo phenyl -2'-4'-disulfonic acid (PPADS) on pore formation and Ca(++) influx were examined in both RPC and 1321rP2X(7)-11. P2X(7)-mediated IL-1beta release in RPC and the effect of PPADS were determined. RPC express functional P2X(7) receptors that were activated by ATP analogs with a rank order of potency of 2'- 3'-O-(4-Benzoylbenzoyl) adenosine 5'-triphosphate (BzATP) > ATP > alpha,beta-methylene ATP. Activation of P2X(7) receptors by BzATP was inhibited by PPADS. Similar results were also obtained in 1321rP2X(7)-11 cells. Activation of P2X(7) receptors on RPC resulted in IL-1 beta secretion, which was inhibited by PPADS. RPC express functional P2X(7) receptors that form pores and mediate the release of IL-1beta.

Metal complexes of the nanosized ligand N-benzoyl-N‧-(p-amino phenyl) thiourea: Synthesis, characterization, antimicrobial activity and the metal uptake capacity of its ligating resin

NASA Astrophysics Data System (ADS)

Elhusseiny, Amel F.; Eldissouky, Ali; Al-Hamza, Ahmed M.; Hassan, Hammed H. A. M.

2015-11-01

The new nanosized N-benzoyl-N‧-(p-amino phenyl) thiourea ligand H2L was synthesized by nanoprecipitation method. The [Cu (H2L)2 Cl]·2H2O, [Zn (H2L)2(OAc)2], [Cd (H2L)2Cl2] and [Hg (H2L)2Cl2] complexes were synthesized and characterized by various physicochemical methods. Results revealed that the ligand act as hypodentate and bonded to the metal ion via the sulfur atom forming mononuclear non-electrolyte diamagnetic complex. Magnetic moment results indicated a reduction of Cu (II) to Cu (I) during the coordination process. Thermal studies demonstrated variable stabilities of the complexes and [Zn (H2L)2(OAc)2] exhibited the highest thermal stability while [Hg (H2L)2Cl2] was volatile. The prepared compounds were screened against different pathogenic microorganisms. The ligand performed high antibacterial activity against certain bacterial strain compared to its complexes, and the standard bacteriocide in use. The ligand was successfully immobilized on modified Amberlite XAD-16 forming the hypodentate ligating resin PS-SO2-H2L. The new resin was characterized and the extent of metal adsorption reached maximum at pH 6.0 for Cu (II), Cd (II) and Ag (I), with an adsorption amount of 4.3, 4.0 and 3.7 mmol g-1 respectively. The nanosized H2L represents a new category of promising adsorbent that would have a practical impact on biological and water treatment applications.

S-phenyl-N-acetylcysteine in urine of rats and workers after exposure to benzene

DOE Office of Scientific and Technical Information (OSTI.GOV)

Jongeneelen, F.J.; Dirven, H.A.; Leijdekkers, C.M.

1987-05-01

An HPLC method for the determination of S-phenyl-N-acetylcysteine in urine is described. The sensitivity is 6 mumol/L (CV = 9%) urine. Exposure of rats to six different concentrations of benzene, ranging from 0-30 ppm, was highly associated with urinary excretion of S-phenyl-N-acetylcysteine (r = 0.86) and with total phenol (r = 0.81). A background level of phenol was found in urine of both non-exposed rats and of non-exposed referents. However, no background excretion of S-phenyl-N-acetylcysteine was found, either in rats or in humans. In urine of exposed rats, the level of S-phenyl-N-acetylcysteine was approximately five times lower than the phenolmore » level. Workers occupationally exposed to benzene, showing high levels of urinary phenol, revealed low concentrations of urinary S-phenyl-N-acetylcysteine. The biological monitoring of industrial exposure to benzene by determination of S-phenyl-N-acetylcysteine in urine is not better than the determination of phenol in urine.« less

X-Ray study of hetero ring flexibility in norbornane, norbornene-fused 1,3-oxazin-2-thiones Structure of 5,8-methano- r-4-phenyl-c-4a, c-5,6,7, c-8, c- 8a-hexahydro-4H- 1 ,3-benzoxazin-2 (3H)-thione

NASA Astrophysics Data System (ADS)

Kálmán, A.; Argay, Gy.; Stájer, G.; Bernáth, G.

1991-08-01

The structure of S,8-methano- r-4-phenyl c4a, c5,6,7 c8 c8ahexahydro4 H 1,3 -benzoxazin- 2 (3 H)-thione (C 15H 17N0S, M r=259.37) has been established by X-ray crystallography from diffractometer data: it crystallizes in the monoclinic space group P2 1/n with a=6.150(2) Å, b=9.655(1) Å, c=22.093(4) Å,β=96.75(2)† V=1302.7(8) Å 3,4,D c=1.32gcm -3and p( Cu K) =20.4cm -. The structure has been solved by direct methods, refined to R=0.050 for 2193 observed reflections. The X-ray analysis substantiated the structure: the NMR spectra in- dicated that the 4-phenyl group assumes an exo-equatorial position. The puckering parameters of D. Cremer, J.A. Pople, J. Am. Chem. Soc., 97 (1975), 1354 (ref.1), of the distorted hetero ring (a transitional form between E 4-envelope, ( 5S 4-screw-boat) show that, depending on the positions of the hetero atoms, both the norbornane, norbornene skeletons markedly alter the characteristic transitional ( 5E/ 5H 6) shape of the 1,3-oxazine ring observed in other saturated, partly saturated l,3-benzoxazin-2-ones, analogous thiones.

Structural Insights into the Atomistic Mechanisms of Action of Small Molecule Inhibitors Targeting the KCa3.1 Channel Pore

PubMed Central

Nguyen, Hai M.; Singh, Vikrant; Pressly, Brandon; Jenkins, David Paul

2017-01-01

The intermediate-conductance Ca2+-activated K+ channel (KCa3.1) constitutes an attractive pharmacological target for immunosuppression, fibroproliferative disorders, atherosclerosis, and stroke. However, there currently is no available crystal structure of this medically relevant channel that could be used for structure-assisted drug design. Using the Rosetta molecular modeling suite we generated a molecular model of the KCa3.1 pore and tested the model by first confirming previously mapped binding sites and visualizing the mechanism of TRAM-34 (1-[(2-chlorophenyl)diphenylmethyl]-1H-pyrazole), senicapoc (2,2-bis-(4-fluorophenyl)-2-phenylacetamide), and NS6180 (4-[[3-(trifluoromethyl)phenyl]methyl]-2H-1,4-benzothiazin-3(4H)-one) inhibition at the atomistic level. All three compounds block ion conduction directly by fully or partially occupying the site that would normally be occupied by K+ before it enters the selectivity filter. We then challenged the model to predict the receptor sites and mechanisms of action of the dihydropyridine nifedipine and an isosteric 4-phenyl-pyran. Rosetta predicted receptor sites for nifedipine in the fenestration region and for the 4-phenyl-pyran in the pore lumen, which could both be confirmed by site-directed mutagenesis and electrophysiology. While nifedipine is thus not a pore blocker and might be stabilizing the channel in a nonconducting conformation or interfere with gating, the 4-phenyl-pyran was found to be a classical pore blocker that directly inhibits ion conduction similar to the triarylmethanes TRAM-34 and senicapoc. The Rosetta KCa3.1 pore model explains the mechanism of action of several KCa3.1 blockers at the molecular level and could be used for structure-assisted drug design. PMID:28126850

Molecular modeling of the inhibition of enzyme PLA2 from snake venom by dipyrone and 1-phenyl-3-methyl-5-pyrazolone

NASA Astrophysics Data System (ADS)

Silva, S. L. Da; Comar, M., Jr.; Oliveira, K. M. T.; Chaar, J. S.; Bezerra, E. R. M.; Calgarotto, A. K.; Baldasso, P. A.; Veber, C. L.; Villar, J. A. F. P.; Oliveira, A. R. M.; Marangoni, S.

Phospholipases A2 (PLA2) are enzymes that trigger the degradation cascade of the arachidonic acid, leading to the formation of pro-inflammatory eicosanoids. The selective inhibition of PLA2s is crucial in the search for a more efficient anti-inflammatory drug with fewer side effects than the drugs currently used. Hence, we studied the influences caused by two pyrazolonic inhibitors: dipyrone (DIP) and 1-phenyl-3-methyl-5-pyrazolone (PMP) on the kinetic behavior of PLA2 from Crotalus adamanteus venom. Molecular modeling results, by DFT and MM approaches, showed that DIP is strongly associated to the active site of PLA2 through three hydrogen bonds, whereas PMP is associated to the enzyme just through hydrophobic interactions. In addition, only PMP presents an intramolecular hydrogen bond that make difficult the formation of more efficient interactions with PLA2. These results help in the understanding of the experimental observations. Experimentally, the results showed that PLA2 from C. adamanteus present a typical Michaelian behavior. In addition, the calculated kinetic parameters showed that, in the presence of DIP or PMP, the maximum enzymatic velocity (VMAX) value was kept constant, whereas the Michaelis constant (KM) values increased and the inhibition constant (KI) decreased, indicating competitive inhibition. These results show that the phenyl-pyrazolonic structures might help in the development and design of new drugs able to selectively inhibit PLA2.

Quaternary ammonium salts substituted by 5-phenyl-1,3,4-oxadiazole-2-thiol as novel antibacterial agents with low cytotoxicity.

PubMed

Wang, Chun-Hua; Xie, Xian-Rui; Liu, Wen-Shuai; Hou, Gui-Ge; Sun, Ju-Feng; Zhao, Feng; Cong, Wei; Li, Hong-Juan; Xin, Wen-Yu

2017-11-01

Twenty-one novel 5-phenyl-1,3,4-oxadiazole-2-thiol (POT) substituted N-hydroxyethyl quaternary ammonium salts (6a-g, 7a-g, 8a-g) were prepared and characterized by FTIR, NMR, and elemental analysis. Compounds 6a, 6c, and 8a were confirmed by X-ray single-crystal diffraction. They display the unsurpassed antibacterial activity against Staphylococcus aureus, α-H-tococcus, Escherichia coli, P. aeruginosa, Proteus vulgaris, Canidia Albicans, especially 6g, 7g, 8g with dodecyl group. Compounds 8a-d with N,N-dihydroxyethyl and POT groups display unsurpassed antibacterial activity and non-toxicity. The structure-activity relationships indicate that POT and flexible dihydroxyethyl group in QAS are necessary for antibacterial activity and cytotoxicity. SEM and TEM images of E. coli morphologies of 8d show the antibacterial agents can adhere to membrane surfaces to inhibit bacterial growth by disrupting peptidoglycan formation and releasing bacterial cytoplasm from cell membranes. © 2017 John Wiley & Sons A/S.

Optical Properties and Junction Characteristics of 6-(5-Bromothiohen-2-yl)-2,3-Dihydro-1-Methyl-3-Oxo-2-Phenyl-1 H-Pyrazolo[4,3-b]Pyridine-5-Carbonitrile Films

NASA Astrophysics Data System (ADS)

Zedan, I. T.; El-Taweel, F. M. A.; Abu El-Enein, R. A. N.; Nawar, H. H.; El-Menyawy, E. M.

2016-11-01

In this study, 6-(5-bromothiohen-2-yl)-2,3-dihydro-1-methyl-3-oxo-2-phenyl-1 H-pyrazolo[4,3-b]pyridine-5-carbonitrile (BDPC) powder was synthesized. BDPC powder showed a polycrystalline structure, whereas the thermally evaporated films had an amorphous structure. The optical parameters such as absorption coefficient and refractive index were calculated in the spectral range 200-500 nm. Spectral distribution analysis of the absorption coefficient revealed that the films had an indirect band transitions with energy gaps of 2.57 eV and 3.5 eV. According to the single oscillator model, the oscillation energy, dispersion energy, and dielectric constant were estimated. The room-temperature current-voltage characteristics of the fabricated Au/BDPC/p-Si/Al heterojunction showed diode-like behavior. The ideality factor, the barrier height and series resistance were determined based on thermionic emission theory and Norde's function. At reverse bias, the current was interpreted in terms of the Schottky and pool-Frenkle effects in low and high voltages, respectively. The built-in voltage, carrier concentration and barrier height were obtained using capacitance-voltage characteristics.

The synthesis and crystal structure of 2-[4(S)-4,5-dihydro-4-phenyl-2-oxazolinyl]-benzenamine, and 2-[4(S)-4,5-dihydro-4-benzyl-2-oxazolinyl]-benzenamine

DOE Office of Scientific and Technical Information (OSTI.GOV)

Mei Luo, E-mail: Lmhh5523385@yahoo.cn; Hai Zhangjia; Hao Yin

2010-12-15

Two oxazolines compound 1a and 1b, 2-[4(S)-4,5-dihydro-4-phenyl-2-ozazolinyl-benzenamine, and (C{sub 15}H{sub 14}N{sub 2}O), 2-[4(S)-4,5-dihydro-4-benzyl-2-ozazolinyl-benzenamine (C{sub 16}H{sub 16}N{sub 2}O) were obtained in moderate yield from the reactions of 2-aminobenzonitrile with optically active L-(+)-Phenylglycinol and L-(+)-Phenylalaninol, respectively, in chlorobenzene under dry, anaerobic conditions. ZnCl{sub 2} was dried under vacuum and acted as a Lewis acid catalyst in this reaction. The structures of 1a and 1b were determined by X-ray diffraction and NMR. There exist intra- and intermolecular N-H-N hydrogen bonds in the crystal structure.

Spectrofluorimetric determination of DL-N-methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine in pharmaceuticals and chitosan solution.

PubMed

Rodrigues, Máira Regina

2012-02-01

A spectrofluorimetric method for the determination of D,L-N-methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine, fluoxetine (F), in pharmaceuticals was evaluated in the 50.0-500.0 μg ml⁻¹ range. Linearity, sensibility, quantification and detection limit, and precision values are satisfactory. The method does not need pre-treatment and was successfully applied to the determination in pharmaceuticals and chitosan (Ch) solution. Ch has an ability to carry and absorb fat and may eventually be used together with F in slimming diets, and then interactions of Ch-F may occur. This work seeks to study these interactions by monitoring the photophysics of a drug in the presence of Ch. The results warn about the care that must be taken when both compounds are prescribed together.

Pharmacokinetic Study of Di-Phenyl-Di-(2,4-Difluobenzohydroxamato)Tin(IV): Novel Metal-Based Complex with Promising Antitumor Potential

PubMed Central

Li, Yunlan; Gao, Zhuyan; Guo, Pu; Li, Qingshan

2012-01-01

Di-phenyl-di-(2,4-difluobenzohydroxamato)tin(IV)(DPDFT), a new metal-based arylhydroxamate antitumor complex, showed high in vivo and in vitro antitumor activity with relative low toxicity, but no data was reported regarding its pharmacokinetics and dependent toxicity. In this paper, a rapid, sensitive, and reproducible HPLC method in vivo using Diamonsil ODS column with a mixture of methanol and phosphoric acid in water (30 : 70, V/V, pH 3.0) as mobile phase was developed and validated for the determination of DPDFT. The plasma was deproteinized with methanol that contained acetanilide as the internal standard (I.S.). The photodiode array detector was set at a wavelength of 228 nm at room temperature and a linear curve over the concentration range 0.1~25 μg·mL−1 (r = 0.9993) was obtained. The method was used to determine the concentration-time profiles for DPDFT in the plasma after single intravenous administration with doses of 5, 10, 15 mg·kg−1 to rats. The pharmacokinetics parameter calculations and modeling were carried out using the 3p97 software. The results showed that the concentration-time curves of DPDFT in rat plasma could be fitted to two-compartment model. PMID:22400014

Induction of apoptosis and cell cycle arrest in L-1210 murine lymphoblastic leukaemia cells by (2E)-3-(2-naphthyl)-1-(3'-methoxy-4'-hydroxy-phenyl)-2-propen-1-one.

PubMed

Pedrini, Fernanda Spezia; Chiaradia, Louise Domeneghini; Licínio, Marley Aparecida; de Moraes, Ana Carolina Rabello; Curta, Juliana Costa; Costa, Aline; Mascarello, Alessandra; Creczinsky-Pasa, Tânia Beatriz; Nunes, Ricardo José; Yunes, Rosendo Augusto; Santos-Silva, Maria Cláudia

2010-09-01

New compounds with biological targets and less cytotoxicity to normal cells are necessary for cancer therapy. In this work ten synthetic chalcones derived from 2-naphtaldehyde were evaluated for their cytotoxic effect in murine acute lymphoblastic leukemia cells L-1210. A series of ten chalcones derived from 2-naphtaldehyde and corresponding acetophenones were prepared by aldolic condensation, using methanol as solvent under basic conditions, at room temperature for 24 h. The cell viability was determined by MTT colorimeter method. The cell cycle phase analysis was carried out by flow cytometry after propidium iodide staining. The apoptosis induction was assessed by exposure to phosphatidylserine (ANNEXIN V-FITC). Cytometric analysis was performed to evaluate the expression of p53, Bcl-2 and Bax protein. The caspase-3 expression was studied by immunoblotting analysis. A preliminary screening of a series of ten chalcones derived from 2-naphtaldehyde showed that chalcone 8, (2E)-3-(2-naphtyl)-1-(3'-methoxy-4'-hydroxy-phenyl)-2-propen-1-one, had the highest cytotoxic effect (IC50 of 54 microM), but not in normal human lymphocytes. To better understand the cytotoxic mechanism of chalcone 8, its effect on cell cycle and apoptosis was assessed. Our results showed that chalcone 8 caused cell cycle arrest in the G2/M phase and a significant increase in the proportion of cells in the subG0/G1 phase. Our results also demonstrated that chalcone 8 promoted a modification in Bax:Bcl-2 ratio and increased p53 expression and caspase-3 activation. The studied chalcone 8 has cytotoxic effect against L-1210 lymphoblastic leukaemic cells, and this effect is associated with increase of p-53 and Bax expression.

Ideal gas thermodynamic properties for the phenyl, phenoxy, and o-biphenyl radicals

NASA Technical Reports Server (NTRS)

Burcat, A.; Zeleznik, F. J.; Mcbride, B. J.

1985-01-01

Ideal gas thermodynamic properties of the phenyl and o-biphenyl radicals, their deuterated analogs and the phenoxy radical were calculated to 5000 K using estimated vibrational frequencies and structures. The ideal gas thermodynamic properties of benzene, biphenyl, their deuterated analogs and phenyl were also calculated.

Effect of prostanoid EP4 receptor antagonist, CJ-042,794, in rat models of pain and inflammation.

PubMed

Murase, Akio; Okumura, Takako; Sakakibara, Ayano; Tonai-Kachi, Hiroko; Nakao, Kazunari; Takada, Junji

2008-02-02

Recent study suggests that the proinflammatory and nociceptive effects of prostaglandin E(2) are mediated by prostanoid receptor subtype EP(4) and prostanoid EP(4) receptor may be a potential target for the treatment of inflammatory pain. Here we describe pharmacological characterization of a novel prostanoid EP(4) receptor antagonist, CJ-042,794 (4-{(1S)-1-[({5-chloro-2-[(4-fluorophenyl) oxy] phenyl} carbonyl) amino] ethyl} benzoic acid) in comparison with piroxicam (non-steroidal anti-inflammatory drug) or rofecoxib (cyclooxygenase-2 inhibitor). CJ-042,794 competitively antagonized cAMP accumulation with a pA(2) value of 8.7 in HEK293 cells overexpressing rat prostanoid EP(4) receptors. Orally administered CJ-042,794 dose-dependently inhibited carrageenan-induced mechanical hyperalgesia with an ED(50) value of 4.7 mg/kg (11 micromol/kg) and its maximal activity was somewhat less effective than that of 10 mg/kg piroxicam (30 micromol/kg p.o.). When CJ-042,794 and rofecoxib were administered to adjuvant-induced arthritis rats on Days 12-22 twice daily, both compounds reversed paw swelling to normal levels. These results suggest that a pharmacological blockade of the prostanoid EP(4) receptor may represent a new therapeutic strategy in signs and symptomatic relief of osteoarthritis and/or rheumatoid arthritis.

The structural properties of 5-methyl-2-phenyl-2H-1,2,3-triazole-4- carboxylic acid and chromogenic mechanism on its rhodamine B derivatives to Hg2+ ions

NASA Astrophysics Data System (ADS)

Li, Jianling; Ding, Guohua; Niu, Yanyan; Wu, Luyong; Feng, Huajie; He, Wenying

2018-07-01

5-Methyl-2-phenyl-2H-1,2,3-triazole-4-carboxylic acid (MPTC), a newly synthesized compound, was explored to study the structural properties and theoretical spectra by using GaussView5.0 program package and the time dependent density functional theory (TD DFT). The calculated quantum chemical values suggested that it is easy for MPTC to lose electron with weak electron accepting ability. And the results of experimental measurements on fluorescence and absorption spectra were consistent with that of the calculated spectra in great degree. In addition, MPTC was successfully used and synthesized a novel rhodamine B derivative RMPTC containing 1,2,3-triazole unit. It is found that there is special chromogenic response of RMPTC to Hg2+ ions in N, N-dimethylformamide (DMF)-H2O (v/v = 1/1, Tris-HCl, pH 7.4) with the triazole appended colorless chemosensor turned to pink and enabled naked-eye detection. The fluorescence signal for RMPTC-Hg2+ system was not affected by other coexisting metal ions. The 1:2 stoichiometric structure of RMPTC and Hg2+ is confirmed using a Job's plot estimation and TD DFT calculations. The corresponding "off-on" fluorescence mechanism of RMPTC binding to Hg2+ which were ascribed to Hg2+ inducing the ring-opened rhodamine B moiety were proposed. This study was an advancement for the application of 1,2,3-triazole compound in photophysical chemistry field and provides guidance for exploring simple and high-selectivity Hg2+ probes in aqueous solutions under physiological conditions.

Reactivities of Substituted α-Phenyl-N-tert-butyl Nitrones

PubMed Central

2015-01-01

In this work, a series of α-phenyl-N-tert-butyl nitrones bearing one, two, or three substituents on the tert-butyl group was synthesized. Cyclic voltammetry (CV) was used to investigate their electrochemical properties and showed a more pronounced substituent effect for oxidation than for reduction. Rate constants of superoxide radical (O2•–) reactions with nitrones were determined using a UV–vis stopped-flow method, and phenyl radical (Ph•) trapping rate constants were measured by EPR spectroscopy. The effect of N-tert-butyl substitution on the charge density and electron density localization of the nitronyl carbon as well as on the free energies of nitrone reactivity with O2•– and HO2• were computationally rationalized at the PCM/B3LYP/6-31+G**//B3LYP/6-31G* level of theory. Theoretical and experimental data showed that the rates of the reaction correlate with the nitronyl carbon charge density, suggesting a nucleophilic nature of O2•– and Ph• addition to the nitronyl carbon atom. Finally, the substituent effect was investigated in cell cultures exposed to hydrogen peroxide and a correlation between the cell viability and the oxidation potential of the nitrones was observed. Through a combination of computational methodologies and experimental methods, new insights into the reactivity of free radicals with nitrone derivatives have been proposed. PMID:24968285

Testing Consent Order on Dilsodecyl Phenyl Phosphite

EPA Pesticide Factsheets

This rule announces that EPA has signed an enforceable Testing Consent Order with three manufacturers of dilsodecyl phenyl phosphite (PDDP CAS No, 25550-98-5), who have agreed to perform certain neurotoxicity tests PDDP.

Crystal structure of bis-(N-methyl-N-phenyl-amino)-tris-ulfane.

PubMed

Barany, George; Henley, Matthew J; Polski, Lauren A; Schroll, Alayne L; Young, Victor G

2015-07-01

The title compound, C14H16N2S3, crystallized with two independent mol-ecules [(1 a ) and (1 b )] in the asymmetric unit. Both mol-ecules display a pseudo-trans conformation. The two consecutive S-S bond lengths of the tris-ulfane unit of mol-ecule (1 a ) are 2.06 (3) and 2.08 (3) Å, and 2.08 (3) and 2.07 (2) Å for mol-ecule (1 b ). Torsion angles about each of the two S-S bonds are 86.6 (2) and 87.0 (2)° for (1 a ), and -84.6 (2) and -85.9 (2)° for (1 b ). The core atoms, viz. the N-S-S-S-N moiety, of the two mol-ecules superimpose well if one is inverted on the other, but the phenyl groups do not. Thus, the two units are essentially conformational enanti-omers. In mol-ecule (1 a ), the two phenyl rings are inclined to one another by 86.7 (3)°, and in mol-ecule (1 b ), by 81.1 (3)°. In the crystal, mol-ecules are linked via C-H⋯π inter-actions, forming sheets lying parallel to (010).

pH-dependent association of SN-38 with lipid bilayers of a novel liposomal formulation.

PubMed

Peikov, Viktor; Ugwu, Sydney; Parmar, Manjeet; Zhang, Allen; Ahmad, Imran

2005-08-11

The aim of this study was to determine the location of SN-38 molecules in a liposomal formulation as a function of pH. Steady-state fluorescence polarization anisotropy and gel filtration studies of blank (placebo) liposomes, liposomes containing SN-38 and SN-38 solutions (in some cases suspensions) were conducted before lyophilization and after re-hydration at different pH conditions. SN-38, l-(4-trimethylammoniumphenyl)-6-phenyl-l,3,5-hexatriene p-toluenesulfonate (TMA-DPH), N-((4-(6-phenyl-l,3,5-hexatrienyl)phenyl)propyl)trimethylammonium p-toluenesulfonate (TMAP-DPH) and l,6-diphenyl-l,3,5-hexatriene (DPH) were used as fluoroprobes in the polarization anisotropy measurements. The localization of SN-38 was governed by the degree of hydrophobicity of the drug molecules. At high pH, SN-38 is in its inactive, hydrophilic form and partitioned into the water phase of the liposome suspensions. In lyophilized LE-SN38 liposomes re-hydrated with low pH buffer, SN-38 was found at the water-lipid interface of the bilayer.

Synthesis, structure characterization and biological studies on a new aromatic hydrazone, 5-(2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)hydrazono)-2,2-dimethyl-1,3-dioxane-4,6-dione, and its transition metal complexes

NASA Astrophysics Data System (ADS)

Kumar, Shubha S.; Biju, S.; Sadasivan, V.

2018-03-01

A new aromatic hydrazone 5-(2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)hydrazono)-2,2-dimethyl-1,3-dioxane-4,6-dione has been synthesized by Japp-Klingemann reaction from diazotized 4-aminoantipyrine and Meldrum's acid. A few 3d-metal ion complexes of this hydrazone were synthesized. The compound and its complexes were characterized by UV-Visible, 1H NMR, ESR, Mass spectral, molar conductance and magnetic susceptibility measurements. The compound was found to exist in hydrazone form in solid state and solution from SXRD and 1H NMR study. The influence of pH on the molecule was studied and found that it shows azo/enol-hydrazone tautomerism in solution. This molecule act as a univalent tridentate ligand and the complexes were assigned to have a 1:2 stoichiometry (M:L). The antioxidant properties of the compounds were explored by DPPH assay and found that the ligand possesses better free radical scavenging effect than the complexes. Antimicrobial activities of these compounds were investigated and were found to be active.

Modelling by partial least squares the relationship between the HPLC mobile phases and analytes on phenyl column.

PubMed

Markopoulou, Catherine K; Kouskoura, Maria G; Koundourellis, John E

2011-06-01

Twenty-five descriptors and 61 structurally different analytes have been used on a partial least squares (PLS) to latent structure technique in order to study chromatographically their interaction mechanism on a phenyl column. According to the model, 240 different retention times of the analytes, expressed as Y variable (log k), at different % MeOH mobile-phase concentrations have been correlated with their theoretical most important structural or molecular descriptors. The goodness-of-fit was estimated by the coefficient of multiple determinations r(2) (0.919), and the root mean square error of estimation (RMSEE=0.1283) values with a predictive ability (Q(2)) of 0.901. The model was further validated using cross-validation (CV), validated by 20 response permutations r(2) (0.0, 0.0146), Q(2) (0.0, -0.136) and validated by external prediction. The contribution of certain mechanism interactions between the analytes, the mobile phase and the column, proportional or counterbalancing is also studied. Trying to evaluate the influence on Y of every variable in a PLS model, VIP (variables importance in the projection) plot provides evidence that lipophilicity (expressed as Log D, Log P), polarizability, refractivity and the eluting power of the mobile phase are dominant in the retention mechanism on a phenyl column. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

8-Chloro-6-iodo-2-phenyl­chromeno[4,3-c]pyrazol-4(2H)-one N,N-dimethyl­formamide monosolvate

PubMed Central

Lokhande, Pradeep; Hasanzadeh, Kamal; Khaledi, Hamid; Mohd Ali, Hapipah

2011-01-01

In the title compound, C16H8ClIN2O2·C3H7NO, the fused tricyclic pyrazolo­coumarin ring and the N-phenyl ring are almost coplanar, the dihedral angle between them being 1.86 (9)°. In the crystal, these rings stack on top of each other via π–π inter­actions [centroid–centroid distances = 3.489 (2), 3.637 (2), 3.505 (2) and 3.662 (2) Å], forming infinite chains along the a axis. The chains are connected into layers parallel to ac plane through I⋯O inter­actions [3.0011 (18) Å] between pairs of symmetry-related mol­ecules. The DMF solvent mol­ecules are C—H⋯O bonded to this network. PMID:21837089

Pharmacological activation of a novel p53-dependent S-phase checkpoint involving CHK-1

PubMed Central

Ahmed, A; Yang, J; Maya-Mendoza, A; Jackson, D A; Ashcroft, M

2011-01-01

We have recently shown that induction of the p53 tumour suppressor protein by the small-molecule RITA (reactivation of p53 and induction of tumour cell apoptosis; 2,5-bis(5-hydroxymethyl-2-thienyl)furan) inhibits hypoxia-inducible factor-1α and vascular endothelial growth factor expression in vivo and induces p53-dependent tumour cell apoptosis in normoxia and hypoxia. Here, we demonstrate that RITA activates the canonical ataxia telangiectasia mutated/ataxia telangiectasia and Rad3-related DNA damage response pathway. Interestingly, phosphorylation of checkpoint kinase (CHK)-1 induced in response to RITA was influenced by p53 status. We found that induction of p53, phosphorylated CHK-1 and γH2AX proteins was significantly increased in S-phase. Furthermore, we found that RITA stalled replication fork elongation, prolonged S-phase progression and induced DNA damage in p53 positive cells. Although CHK-1 knockdown did not significantly affect p53-dependent DNA damage or apoptosis induced by RITA, it did block the ability for DNA integrity to be maintained during the immediate response to RITA. These data reveal the existence of a novel p53-dependent S-phase DNA maintenance checkpoint involving CHK-1. PMID:21593792

In Vitro Studies on a Microfluidic Sensor with Embedded Obstacles Using New Antibacterial Synthetic Compounds (1-TDPPO) Mixed Prop-2-en-1-one with Difluoro Phenyl.

PubMed

Roh, Changhyun; Lee, Jaewoong; Kinger, Mayank; Kang, Chankyu

2017-04-08

This paper describes the use of an analytical microfluidic sensor for accelerating chemo-repellent response and strong anti-bacterial 1-(Thien-2-yl)-3-(2, 6-difluoro phenyl) prop-2-en-1-one (1-TDPPO). The chemically-synthesized antimicrobial agent, which included prop-2-en-1-one and difluoro phenyl groups, was moving through an optically transparent polydimethylsiloxane (PDMS) microfluidic sensor with circular obstacles arranged evenly. The response, growth and distribution of fluorescent labeling Pseudomonas aeruginosa PAO1 against the antimicrobial agent were monitored by confocal laser scanning microscope (CLSM). The microfluidic sensor along with 1-TDPPOin this study exhibits the following advantages: (i) Real-time chemo-repellent responses of cell dynamics; (ii) Rapid eradication of biofilm by embedded obstacles and powerful antibacterial agents, which significantly reduce the response time compared to classical methods; (iii) Minimal consumption of cells and antimicrobial agents; and (iv) Simplifying the process of the normalization of the fluorescence intensity and monitoring of biofilm by captured images and datasets.

Characterization of the covalent binding of N-phenyl-N'-(2-chloroethyl)ureas to {beta}-tubulin: importance of Glu198 in microtubule stability.

PubMed

Fortin, Sébastien; Bouchon, Bernadette; Chambon, Christophe; Lacroix, Jacques; Moreau, Emmanuel; Chezal, Jean-Michel; Degoul, Françoise; C-Gaudreault, René

2011-02-01

N-Phenyl-N'-(2-chloroethyl)ureas (CEUs) are antimicrotubule agents interacting covalently with β-tubulin near the colchicine-binding site (C-BS). Glutamyl 198 residue in β-tubulin (Glu198), which is adjacent to the C-BS behind the two potent nucleophilic residues, Cys239 and Cys354, has been shown to covalently react with 1-(2-chloroethyl)-3-(4-iodophenyl)urea (ICEU). By use of mass spectrometry, we have now identified residues in β-tubulin that have become modified irreversibly by 1-(2-chloroethyl)-3-[3-(5-hydroxypentyl)phenyl]urea (HPCEU), 1-[4-(3-hydroxy-4-methoxystyryl)phenyl]-3-(2-chloroethyl)urea (4ZCombCEU), and N,N'-ethylenebis(iodoacetamide) (EBI). The binding of HPCEU and 4ZCombCEU to β-tubulin resulted in the acylation of Glu198, a protein modification of uncommon occurrence in living cells. Prototypical CEUs then were used as molecular probes to assess, in mouse B16F0 and human MDA-MB-231 cells, the role of Glu198 in microtubule stability. For that purpose, we studied the effect of Glu198 modification by ICEU, HPCEU, and 4ZCombCEU on the acetylation of Lys40 on α-tubulin, a key indicator of microtubule stability. We show that modification of Glu198 by prototypical CEUs correlates with a decrease in Lys40 acetylation, as observed also with other microtubule depolymerizing agents. Therefore, CEU affects the stability and the dynamics of microtubule, likewise a E198G mutation, which is unusual for xenobiotics. We demonstrate for the first time that EBI forms an intramolecular cross-link between Cys239 and Cys354 of β-tubulin in living cells. This work establishes a novel basis for the development of future chemotherapeutic agents and provides a framework for the design of molecules useful for studying the role of Asp and Glu residues in the structure/function and the biological activity of several cellular proteins under physiological conditions.

Computer-aided insights into receptor-ligand interaction for novel 5-arylhydantoin derivatives as serotonin 5-HT7 receptor agents with antidepressant activity.

PubMed

Kucwaj-Brysz, Katarzyna; Kurczab, Rafał; Jastrzębska-Więsek, Magdalena; Żesławska, Ewa; Satała, Grzegorz; Nitek, Wojciech; Partyka, Anna; Siwek, Agata; Jankowska, Agnieszka; Wesołowska, Anna; Kieć-Kononowicz, Katarzyna; Handzlik, Jadwiga

2018-03-10

This paper presents a computer-aided insight into the receptor-ligand interaction for novel analogs of the lead structure 5-(4-fluorophenyl)-3-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-5-methylimidazolidine-2,4-dione (1, MF-8), as part of the search for potent and selective serotonin 5-HT 7 receptor (5-HT 7 R) agents. New hydantoin derivatives (4-19) were designed and synthesized. For 5-phenyl-3-(2-hydroxy-3-(4-(2-ethoxyphenyl)piperazin-1-yl)propyl)-5-methylimidazolidine-2,4-dione (4), its crystal structure was determined experimentally. Molecular modeling studies were performed, including both pharmacophore and structure-based approaches. New compounds were investigated in radioligand binding assays (RBA) for their affinity toward 5-HT 7 R and selectivity over 5-HT 1A R, dopamine D 2 R and α 1 -, α 2 -and β-adrenoceptors. Selected compounds (5-8) were assessed for their antidepressant and anxiolytic effects in vivo in mice. Most of the tested compounds displayed potent affinity and selectivity for 5-HT 7 R in RBA, in particular seven compounds (4, 5, 7, 8 and 10-12,K i  ≤ 10 nM). Antidepressant-like activity in vivo for all tested compounds (5-8) was confirmed. SAR analysis based on both crystallography-supported molecular modeling and RBA results indicated that mono-phenyl substituents at both hydantoin and piperazine are more favorable for 5-HT 7 R affinity than the di-phenyl ones. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Synthesis, growth, structural, optical, luminescence, surface and HOMO LUMO analysis of 2-[2-(4-cholro-phenyl)-vinyl]-1-methylquinolinium naphthalene-2-sulfonate organic single crystals grown by a slow evaporation technique

NASA Astrophysics Data System (ADS)

Karthigha, S.; Kalainathan, S.; Maheswara Rao, Kunda Uma; Hamada, Fumio; Yamada, Manabu; Kondo, Yoshihiko

2016-02-01

Single crystals of 2-[2-(4-cholro-phenyl)-vinyl]-1-methylquinolinium naphthalene-2-sulfonate (4CLNS) were grown by a slow evaporation technique. The formation of molecule was confirmed from 1H NMR and FTIR analysis. The confirmation of crystal structure was done by single crystal XRD and atomic packing of grown crystal was identified. The grown single crystal crystallized in triclinic structure with centrosymmetric space group P-1. The crystalline nature of the synthesised material was recorded by powder XRD. The optical absorption properties of the grown crystals were analyzed by UV-vis spectral studies. The thermal behaviour of the title material has been studied by TG/DTA analysis which revealed the stability of the compound till its melting point 276.7 °C. The third order nonlinear optical property of 4CLNS was investigated in detail by Z scan technique and it confirms that the title crystal is suitable for photonic devices and NLO optical applications. Emissions at 519 nm in green region of the EM spectrum were found by photoluminescence studies. The charge transfer occurring within the molecule is explained by the calculated HOMO and LUMO energies.

Crystal structure of 3-({[(morpholin-4-yl)carbono-thio-yl]sulfan-yl}acet-yl)phenyl benzoate.

PubMed

Ambekar, Sachin P; Mahesh Kumar, K; Shirahatti, Arun Kumar M; Kotresh, O; Anil Kumar, G N

2014-11-01

In the title compound, C20H19NO4S2, the morpholine ring adopts the expected chair conformation. The central phenyl ring makes dihedral angles of 67.97 (4) and 7.74 (3)°, respectively, with the benzoate phenyl ring and the morpholine mean plane. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming zigzag chains along the b-axis direction. C-H⋯π inter-actions link centrosymmetrically related mol-ecules, reinforcing the three-dimensional structure.

78 FR 63938 - Receipt of Several Pesticide Petitions Filed for Residues of Pesticide Chemicals in or on Various...

Federal Register 2010, 2011, 2012, 2013, 2014

2013-10-25

...]-(2-fluorophenyl)-[alpha]- (4-fluorophenyl)-1 H-1,2,4-triazole-1-ethanol], including its metabolites...-fluorophenyl)-1 H-1,2,4-triazole-1-ethanol], including its metabolites and degradates, in or on African tree... saflufenacil, including its metabolites and degradates, in or on grass, forage at 15 ppm; grass, hay at 20 ppm...

Selenorhodamine Photosensitizers for Photodynamic Therapy of P-Glycoprotein-Expressing Cancer Cells

PubMed Central

2015-01-01

We examined a series of selenorhodamines with amide and thioamide functionality at the 5-position of a 9-(2-thienyl) substituent on the selenorhodamine core for their potential as photosensitizers for photodynamic therapy (PDT) in P-glycoprotein (P-gp) expressing cells. These compounds were examined for their photophysical properties (absorption, fluorescence, and ability to generate singlet oxygen), for their uptake into Colo-26 cells in the absence or presence of verapamil, for their dark and phototoxicity toward Colo-26 cells, for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their colocalization with mitochondrial specific agents in Colo-26 cells. Thioamide derivatives 16b and 18b were more effective photosensitizers than amide derivatives 15b and 17b. Selenorhodamine thioamides 16b and 18b were useful in a combination therapy to treat Colo-26 cells in vitro: a synergistic therapeutic effect was observed when Colo-26 cells were exposed to PDT and treatment with the cancer drug doxorubicin. PMID:25250825

2-(4-Ethoxy phenyl)-4-phenyl quinoline organic phosphor for solution processed blue organic light-emitting diodes.

PubMed

Ghate, Minakshi; Kalyani, N Thejo; Dhoble, S J

2018-05-31

This paper reports the synthesis and characterization of 2-(4-ethoxyphenyl)-4-phenyl quinoline (OEt-DPQ) organic phosphor using an acid-catalyzed Friedlander reaction and the preparation of blended thin films by molecularly doping OEt-DPQ in poly(methyl methacrylate) (PMMA) at different wt%. The molecular structure of the synthesized phosphor was confirmed by Fourier transform infra-red (FTIR) spectroscopy and nuclear magnetic resonance spectra (NMR). Surface morphology and percent composition of the elements were assessed by scanning electron microscopy (SEM) and energy dispersive analysis of X-rays (EDAX). The thermal stability and melting point of OEt-DPQ and thin films were probed by thermo-gravimetric analysis (TGA)/differential thermal analysis (DTA) and were found to be 80°C and 113.6°C, respectively. UV-visible optical absorption spectra of OEt-DPQ in the solid state and blended films produced absorption bands in the range 260-340 nm, while photoluminescence (PL) spectra of OEt-DPQ in the solid state and blended thin films demonstrated blue emission that was registered at 432 nm when excited at 363-369 nm. However, solvated OEt-DPQ in chloroform, tetrahydrofuran or dichloromethane showed a blue shift of 31-43 nm. Optical absorption and emission parameters such as molar extinction coefficient (ε), energy gap (E g ), transmittance (T), reflectance (R), refractive index (n), oscillator energy (E 0 ) and oscillator strength (f), quantum yield (φ f ), oscillator energy (E 0 ), dispersion energy (E d ), Commission Internationale de l'Éclairage (CIE) co-ordinates and energy yield fluorescence (E F ) were calculated to assess the phosphor's suitability as a blue emissive material for opto-electronic applications such as organic light-emitting diodes (OLEDs), flexible displays and solid-state lighting technology. Copyright © 2018 John Wiley & Sons, Ltd.

Improving Nonspecific Binding and Solubility: Bicycloalkyl Groups and Cubanes as para-Phenyl Bioisosteres.

PubMed

Auberson, Yves P; Brocklehurst, Cara; Furegati, Markus; Fessard, Thomas C; Koch, Guido; Decker, Andrea; La Vecchia, Luigi; Briard, Emmanuelle

2017-04-20

Bicycloalkyl groups have been previously described as phenyl group bioisosteres. This article describes the synthesis of new building blocks allowing their introduction into complex molecules, and explores their use as a means to modify the physicochemical properties of drug candidates and improve the quality of imaging agents. In particular, the replacement of an aromatic ring with a bicyclo[1.1.1]pentane-1,3-diyl (BCP) group improves aqueous solubility by at least 50-fold, and markedly decreases nonspecific binding (NSB) as measured by CHI(IAM), the chromatographic hydrophobicity index on immobilized artificial membranes. Structural variations with the bicyclo[2.2.2]octane-1,4-diyl group led to more lipophilic molecules and did not show the same benefits regarding NSB or solubility, whereas substitutions with cubane-1,4-diyl showed improvements for both parameters. These results confirm the potential advantages of both BCP and cubane motifs as bioisosteric replacements for optimizing para-phenyl-substituted molecules. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Effect of Crystallizable Solvent on Phase Separation and Charge Transport in Polymer-fullerene Films

NASA Astrophysics Data System (ADS)

Kaewprajak, A.; Lohawet, K.; Wutikhun, T.; Meemuk, B.; Kumnorkaew, P.; Sagawa, T.

2017-09-01

The effect of 1,3,5-trichlorobenzene (TCB) as crystallizable solvent on poly[N-9‧-heptadecanyl-2,7-carbazole-alt-5,5-(4‧,7‧-di-2-thienyl-2‧,1‧,3‧-benzothiadiazole)] (PCDTBT) and [6,6]-phenyl C71 butyric acid methyl ester (PC71BM) bulk heterojunction (BHJ) was investigated. We found that phase separation of PCDTBT and PC71BM and formation of the condensed network of polymers were appropriately regulated by addition of TCB in the BHJ films, which were confirmed by optical microscopic, AFM, and TEM observations in addition to current-voltage analyses. Through the formation of a good continuous pathway for carrier transport by the addition of TCB, 2.5 times enhancement of the hole mobility in the BHJ film was attained from 5.82 × 10-5 cm2 V-1 s-1 without TCB to 1.48 × 10-4 cm2 V-1 s-1 with 20 mg ml-1 of TCB.

Conformational Aspects of the O-acetylation of C-tetra(phenyl)calixpyrogallol[4]arene.

PubMed

Casas-Hinestroza, José Luis; Maldonado, Mauricio

2018-05-20

Reaction between pyrogallol and benzaldehyde results in a conformational mixture of C- tetra(phenyl)pyrogallol[4]arene (crown and chair). The conformer mixture was separated using crystallization procedures and the structures were determined using FTIR, ¹H-NMR, and 13 C-NMR. O -acetylation of C- tetra(phenyl)pyrogallol[4]arene (chair) with acetic anhydride, in pyridine results in the formation of dodecaacetyl-tetra(phenyl)pyrogallol[4]arene. The structure was determined using ¹H-NMR and 13 C-NMR finding that the product maintains the conformation of the starting conformer. On the other hand, the O -acetylation reaction of C- tetra(phenyl)pirogallol[4]arene (crown) under same conditions proceeded efficiently, and its structure was determined using ¹H-NMR and 13 C-NMR. Dynamic ¹H-NMR of acetylated pyrogallolarene was studied by means of variable temperature in DMSO- d ₆ solution, and it revealed that two conformers are formed in the solution. Boat conformations for acetylated pyrogallolarene showed a slow interconversion at room temperature.

Synthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors

PubMed Central

Binyamin, Iris; Meidan-Shani, Shoval

2015-01-01

Summary The synthesis of P-chirogenic (±)-phosphine oxides and phosphinates via selective nucleophilic ring opening of the corresponding oxaphospholanes is described. Two representative substrates: the phosphonate 2-ethoxy-1,2-oxaphospholane 2-oxide and the phosphinate 2-phenyl-1,2-oxaphospholane 2-oxide were reacted with various Grignard reagents to produce a single alkyl/aryl product. These products may possess further functionalities in addition to the phosphorus center such as the γ-hydroxypropyl group which results from the ring opening and π-donor moieties such as aryl, allyl, propargyl and allene which originates from the Grignard reagent. PMID:26425187

Photoinduced intramolecular charge transfer and photophysical characteristics of (2Z)-3-[4-(dimethylamino) phenyl]-2-(2-methylphenyl) prop-2-ene-nitrile (DPM) in different media

NASA Astrophysics Data System (ADS)

Asiri, Abdullah M.; El-Daly, Samy A.; Alamry, Khalid A.; Arshad, Muhammad Nadeem; Pannipara, Mehboobali

2015-10-01

A new fluorophore, (2Z)-3-[4-(dimethylamino) phenyl]-2-(2-methylphenyl) prop-2-ene-nitrile (DPM), was synthesized by knoevenagel condensation of 4-(dimethylamino) benzaldehyde and 2-methylbenzyl cyanide in ethanol using NaOH as base. The electronic absorption and emission characteristic of DPM was studied in different solvents. The X-ray crystallographic structure of DPM was also investigated. A crystalline solid of DPM gives a strong green emission at about 533 nm; these phenomena are important for the application of DPM dye in organic photo emitting diode. DPM exhibits a red shift in its emission spectrum as solvent polarity increases, indicating a large change in the dipole moment of dye molecule upon excitation due to intramolecular charge transfer in excited DPM*. The fluorescence quantum yield depends strongly on the properties of the solvents, which was attributed to positive and negative solvatokinetic effects. The DPM dye displays solubilization in cationic (CTAB) micelle and could be used as a probe to determine the critical micelle concentration (CMC) of CTAB.

1-(2-Hydroxy-5-methylphenyl)-3-phenyl-1,3-propanedione Induces G1 Cell Cycle Arrest and Autophagy in HeLa Cervical Cancer Cells.

PubMed

Tsai, Jie-Heng; Hsu, Li-Sung; Huang, Hsiu-Chen; Lin, Chih-Li; Pan, Min-Hsiung; Hong, Hui-Mei; Chen, Wei-Jen

2016-08-05

The natural agent, 1-(2-hydroxy-5-methylphenyl)-3-phenyl-1,3-propanedione (HMDB), has been reported to have growth inhibitory effects on several human cancer cells. However, the role of HMDB in cervical cancer remains unclear. Herein, we found that HMDB dose- and time-dependently inhibited growth of HeLa cervical cancer cells, accompanied with G1 cell cycle arrest. HMDB decreased protein expression of cyclins D1/D3/E and cyclin-dependent kinases (CDKs) 2/4/6 and reciprocally increased mRNA and protein levels of CDK inhibitors (p15, p16, p21, and p27), thereby leading to the accumulation of hypophosphorylated retinoblastoma (Rb) protein. HMDB also triggered the accumulation of acidic vesicles and formation of microtubule-associated protein-light chain 3 (LC3), followed by increased expression of LC3 and Beclin-1 and decreased expression of p62, suggesting that HMDB triggered autophagy in HeLa cells. Meanwhile, suppression of the expression of survivin and Bcl-2 implied that HMDB-induced autophagy is tightly linked to apoptosis. Exploring the action mechanism, HMDB induced autophagy via the modulation of AMP-activated protein kinase (AMPK) and mTOR signaling pathway rather than the class III phosphatidylinositol 3-kinase pathway. These results suggest that HMDB inhibits HeLa cell growth by eliciting a G1 arrest through modulation of G1 cell cycle regulators and by concomitantly inducing autophagy through the mediation of AMPK-mTOR and Akt-mTOR pathways, and may be a promising antitumor agent against cervical cancer.

Phenyl-β-D-glucopyranoside and Phenyl-β-D-galactopyranoside dimers: Small Structural differences but Very Different Interactions

NASA Astrophysics Data System (ADS)

Usabiaga, Imanol; Camiruaga, Ander; Insausti, Aran; Çarçabal, Pierre; Cocinero, Emilio J.; León, Iker; Fernández, José A.

2018-02-01

We report a combination of laser spectroscopy in molecular jets and quantum mechanical calculations to characterize the aggregation preferences of phenyl-β-D-glucopyranoside (β-PhGlc) and phenyl-β-D-galactopyranoside (β-PhGal) homodimers. At least two structures of β-PhGlc dimer were found maintaining the same intramolecular interactions of the monomers, but with additional intermolecular interactions between the hydroxyl groups. Several isomers were also found for the dimer of β-PhGal forming extensive hydrogen bond networks between the interacting molecules, of very different shape. All the species found present several CH•••Pi and OH•••Pi interactions that add stability to the aggregates. The results show how even the smallest change in a substituent, from axial to equatorial position, plays a decisive role in the formation of the dimers. These conclusions reinforce the idea that the small structural changes between sugar units are amplified by formation of intra and intermolecular hydrogen bond networks, helping other molecules (proteins, receptors) to easily read the sugar code of glycans.

(2R,3S,4R)-3,4-Isopropyl­idenedi­oxy-2-(phenyl­sulfonyl­meth­yl)pyrrolidin-1-ol

PubMed Central

Flores, Mari Fe; Garcia, Pilar; M. Garrido, Narciso; Sanz, Francisca; Diez, David

2012-01-01

The title compound, C14H19NO5S, was prepared by nucleophilic addition of the lithium derivative of methyl­phenyl­sulfone to (3S,4R)-3,4-isopropyl­idene­dioxy­pyrroline 1-oxide. There are four mol­ecules in the asymmetric unit. The crystal structure determination confirms the configuration of the chiral centres as 2R,3S,4R. In the crystal, pairs of O—H⋯N hydrogen bonds link the mol­ecules into dimers. PMID:22904989

Understanding the Thickness-Dependent Performance of Organic Bulk Heterojunction Solar Cells: The Influence of Mobility, Lifetime, and Space Charge.

PubMed

Kirchartz, Thomas; Agostinelli, Tiziano; Campoy-Quiles, Mariano; Gong, Wei; Nelson, Jenny

2012-12-06

We investigate the reasons for the dependence of photovoltaic performance on the absorber thickness of organic solar cells using experiments and drift-diffusion simulations. The main trend in photocurrent and fill factor versus thickness is determined by mobility and lifetime of the charge carriers. In addition, space charge becomes more and more important the thicker the device is because it creates field free regions with low collection efficiency. The two main sources of space-charge effects are doping and asymmetric mobilities. We show that for our experimental results on Si-PCPDTBT:PC71BM (poly[(4,40-bis(2-ethylhexyl)dithieno[3,2-b:20,30-d]silole)-2,6-diyl-alt-(4,7-bis(2-thienyl)-2,1,3-benzothiadiazole)-5,50-diyl]:[6,6]-phenyl C71-butyric acid methyl ester) solar cells, the influence of doping is most likely the dominant influence on the space charge and has an important effect on the thickness dependence of performance.

40 CFR 721.9825 - Phenyl substituted triazolinones.

Code of Federal Regulations, 2013 CFR

2013-07-01

... in combination with a chemical-resistant glove that has been demonstrated (EPA review not required... SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.9825 Phenyl substituted triazolinones. (a) Chemical substance and significant new uses...

40 CFR 721.9825 - Phenyl substituted triazolinones.

Code of Federal Regulations, 2011 CFR

2011-07-01

... in combination with a chemical-resistant glove that has been demonstrated (EPA review not required... SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.9825 Phenyl substituted triazolinones. (a) Chemical substance and significant new uses...

40 CFR 721.9825 - Phenyl substituted triazolinones.

Code of Federal Regulations, 2012 CFR

2012-07-01

... in combination with a chemical-resistant glove that has been demonstrated (EPA review not required... SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.9825 Phenyl substituted triazolinones. (a) Chemical substance and significant new uses...

40 CFR 721.9825 - Phenyl substituted triazolinones.

Code of Federal Regulations, 2014 CFR

2014-07-01

... in combination with a chemical-resistant glove that has been demonstrated (EPA review not required... SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.9825 Phenyl substituted triazolinones. (a) Chemical substance and significant new uses...

Is there evidence for man-made nanoparticles in the Dutch environment?

PubMed

Bäuerlein, Patrick S; Emke, Erik; Tromp, Peter; Hofman, Jan A M H; Carboni, Andrea; Schooneman, Ferry; de Voogt, Pim; van Wezel, Annemarie P

2017-01-15

Only very limited information is available on measured environmental concentrations of nanoparticles. In this study, several environmental compartments in The Netherlands were probed for the presence of nanoparticles. Different types of water were screened for the presence of inorganic (Ag, Au, TiO 2 ) and organic nanoparticles (C 60 , C 70 , [6,6]-phenyl-C 61 -butyric acid octyl ester, [6,6]-phenyl-C 61 -butyric acid butyl ester, [6,6]-phenyl-C 61 -butyric acid methyl ester, [6,6]-bis-phenyl-C 61 -butyric acid methyl ester, [6,6]-phenyl-C 71 -butyric acid methyl ester, [6,6]-thienyl-C 61 -butyric acid methyl ester). Air samples were analysed for the presence of nanoparticulate Mo, Ag, Ce, W, Pd, Pt, Rh, Zn, Ti, Si, B as well as Fe and Cu. ICP-MS, Orbitrap-HRMS, SEM and EDX were used for this survey. Water samples included dune and bank filtrates, surface waters and ground waters as well as influents, effluents and sludge of sewage treatment plants (STPs), and surface waters collected near airports and harbours. Air samples included both urban and rural samples. C 60 was detected in air, sewage treatment plants, influents, effluents and sludge, but in no other aqueous samples despite the low detection limit of 0.1ng/L. C 70 and functionalised fullerenes were not detected at all. In STP sludge and influent the occurrence of Ag and Au nanoparticles was verified by SEM/EDX and ICP-MS. In air up to about 25m% of certain metals was found in the nanosize fraction. Overall, between 1 and 6% of the total mass from metals in the air samples was found in the size fraction <100nm. Copyright © 2016 Elsevier B.V. All rights reserved.

Syntheses, structures and properties of two new coordination polymers based on D-camphoric acid and 2-phenyl-4,6-diamino-1,3,5-triazine

DOE Office of Scientific and Technical Information (OSTI.GOV)

Lun, Huijie; Yang, Jinghe; Jin, Linyu

2015-05-15

By hydrothermal method, two new coordination polymers [Co(ca)(phdat)]{sub n} (1), [Ni(ca)(phdat).0.125H{sub 2}O]{sub n} (2) (H{sub 2}ca=D-camphoric acid, phdat=2-phenyl-4,6-diamino-1,3,5-triazine) have been achieved and structurally characterized by IR, elemental analyses, X-ray single-crystal diffraction and TGA. The X-ray single-crystal diffraction reveals that compounds 1 and 2 are isostructural, both of which exhibit two-dimensional layered network built up from paddle-wheel Co{sub 2}(CO{sub 2}){sub 4}/Ni{sub 2}(CO{sub 2}){sub 4} SBUs by ca{sup 2−} ligand. In the existence of π…π stacking interactions between triazine rings and phenyl rings, the 3D networks are constructed with the hanging phdat filled between the neighboring layers. Furthermore, compounds 1–2 exhibit antiferromagneticmore » behavior and compound 2 displays a good activity for methanol oxidation. - Graphical abstract: Two new coordination compounds 1–2 have been synthesized and characterized by single-crystal X-ray diffractions, IR spectra, elemental analyses, thermogravimetric analyses, magnetic and electrochemical measurement. - Highlights: • This paper reports two new coordination polymers based on D-camphoric acid. • Both the compounds feather two-dimensional layered networks built up from paddle-wheel SBUs. • The magnetism and electrochemical property are investigated.« less

In Vitro Effects of the Endocrine Disruptor p,p'-DDT on Human Follitropin Receptor.

PubMed

Munier, Mathilde; Grouleff, Julie; Gourdin, Louis; Fauchard, Mathilde; Chantreau, Vanessa; Henrion, Daniel; Coutant, Régis; Schiøtt, Birgit; Chabbert, Marie; Rodien, Patrice

2016-07-01

1-chloro-4-[2,2,2-trichloro-1-(4-chlorophenyl)ethyl]benzene (p,p'-DDT) is a persistent environmental endocrine disruptor (ED). Several studies have shown an association between p,p'-DDT exposure and reproductive abnormalities. To investigate the putative effects of p,p'-DDT on the human follitropin receptor (FSHR) function. We used Chinese hamster ovary (CHO) cells stably expressing human FSHR to investigate the impact of p,p'-DDT on FSHR activity and its interaction with the receptor. At a concentration of 5 μM p,p'-DDT increased the maximum response of the FSHR to follitropin by 32 ± 7.45%. However, 5 μM p,p'-DDT decreased the basal activity and did not influence the maximal response of the closely related LH/hCG receptor to human chorionic gonadotropin (hCG). The potentiating effect of p,p'-DDT was specific for the FSHR. Moreover, in cells that did not express FSHR, p,p'-DDT had no effect on cAMP response. Thus, the potentiating effect of p,p'-DDT was dependent on the FSHR. In addition, p,p'-DDT increased the sensitivity of FSHR to hCG and to a low molecular weight agonist of the FSHR, 3-((5methyl)-2-(4-benzyloxy-phenyl)-5-{[2-[3-ethoxy-4-methoxy-phenyl)-ethylcarbamoyl]-methyl}-4-oxo-thiazolidin-3-yl)-benzamide (16a). Basal activity in response to p,p'-DDT and potentiation of the FSHR response to FSH by p,p'-DDT varied among FSHR mutants with altered transmembrane domains (TMDs), consistent with an effect of p,p'-DDT via TMD binding. This finding was corroborated by the results of simultaneously docking p,p'-DDT and 16a into the FSHR transmembrane bundle. p,p'-DDT acted as a positive allosteric modulator of the FSHR in our experimental model. These findings suggest that G protein-coupled receptors are additional targets of endocrine disruptors. Munier M, Grouleff J, Gourdin L, Fauchard M, Chantreau V, Henrion D, Coutant R, Schiøtt B, Chabbert M, Rodien P. 2016. In vitro effects of the endocrine disruptor p,p'-DDT on human follitropin receptor. Environ Health

Enhanced third-order nonlinear optical properties determined in thin films using the Z-scan technique: bis(μ-4,4'-oxydibenzoato)bis[(4'-phenyl-2,2':6',2''-terpyridine)cobalt(II)].

PubMed

Liu, Runqiang; Zhao, Ning; Liu, Ping; An, Caixia; Lian, Zhaoxun

2016-05-01

π-Conjugated organic materials exhibit high and tunable nonlinear optical (NLO) properties, and fast response times. 4'-Phenyl-2,2':6',2''-terpyridine (PTP) is an important N-heterocyclic ligand involving π-conjugated systems, however, studies concerning the third-order NLO properties of terpyridine transition metal complexes are limited. The title binuclear terpyridine Co(II) complex, bis(μ-4,4'-oxydibenzoato)-κ(3)O,O':O'';κ(3)O'':O,O'-bis[(4'-phenyl-2,2':6',2''-terpyridine-κ(3)N,N',N'')cobalt(II)], [Co2(C14H8O5)2(C21H15N3)2], (1), has been synthesized under hydrothermal conditions. In the crystal structure, each Co(II) cation is surrounded by three N atoms of a PTP ligand and three O atoms, two from a bidentate and one from a symmetry-related monodentate 4,4'-oxydibenzoate (ODA(2-)) ligand, completing a distorted octahedral coordination geometry. Neighbouring [Co(PTP)](2+) units are bridged by ODA(2-) ligands to form a ring-like structure. The third-order nonlinear optical (NLO) properties of (1) and PTP were determined in thin films using the Z-scan technique. The title compound shows a strong third-order NLO saturable absorption (SA), while PTP exhibits a third-order NLO reverse saturable absorption (RSA). The absorptive coefficient β of (1) is -37.3 × 10(-7) m W(-1), which is larger than that (8.96 × 10(-7) m W(-1)) of PTP. The third-order NLO susceptibility χ((3)) values are calculated as 6.01 × 10(-8) e.s.u. for (1) and 1.44 × 10(-8) e.s.u. for PTP.

Three-dimensional carbon allotropes comprising phenyl rings and acetylenic chains in sp+ sp 2 hybrid networks

DOE Office of Scientific and Technical Information (OSTI.GOV)

Wang, Jian -Tao; Chen, Changfeng; Li, Han -Dong

Here, we here identify by ab initio calculations a new type of three-dimensional (3D) carbon allotropes that consist of phenyl rings connected by linear acetylenic chains in sp+ sp 2 bonding networks. These structures are constructed by inserting acetylenic or diacetylenic bonds into an all sp 2-hybridized rhombohedral polybenzene lattice, and the resulting 3D phenylacetylene and phenyldiacetylene nets comprise a 12-atom and 18-atom rhombohedral primitive unit cells R - 3m symmetry, which are characterized as the 3D chiral crystalline modification of 2D graphyne and graphdiyne, respectively. Simulated phonon spectra reveal that these structures are dynamically stable. Electronic band calculations indicatemore » that phenylacetylene is metallic, while phenyldiacetylene is a semiconductor with an indirect band gap of 0.58 eV. The present results establish a new type of carbon phases and offer insights into their outstanding structural and electronic properties.« less

Three-dimensional carbon allotropes comprising phenyl rings and acetylenic chains in sp+ sp 2 hybrid networks

DOE PAGES

Wang, Jian -Tao; Chen, Changfeng; Li, Han -Dong; ...

2016-04-18

Here, we here identify by ab initio calculations a new type of three-dimensional (3D) carbon allotropes that consist of phenyl rings connected by linear acetylenic chains in sp+ sp 2 bonding networks. These structures are constructed by inserting acetylenic or diacetylenic bonds into an all sp 2-hybridized rhombohedral polybenzene lattice, and the resulting 3D phenylacetylene and phenyldiacetylene nets comprise a 12-atom and 18-atom rhombohedral primitive unit cells R - 3m symmetry, which are characterized as the 3D chiral crystalline modification of 2D graphyne and graphdiyne, respectively. Simulated phonon spectra reveal that these structures are dynamically stable. Electronic band calculations indicatemore » that phenylacetylene is metallic, while phenyldiacetylene is a semiconductor with an indirect band gap of 0.58 eV. The present results establish a new type of carbon phases and offer insights into their outstanding structural and electronic properties.« less

The crystal structure of a new ferrocenyl P,N ligand: 1-[(2,2-di­methyl­hydrazin-1-yl­idene)meth­yl]-1′-(di­phenyl­phospho­rothio­yl)ferrocene

PubMed Central

Mouas, Toma Nardjes; Daran, Jean-Claude; Merazig, Hocine

2018-01-01

The asymmetric unit of the title compound, [Fe(C8H11N2)(C17H14PS)], contains two independent mol­ecules (A and B) with very similar conformations. Each mol­ecule is built up from a ferrocene unit substituted in the 1 and 1′ positions by a protected sulfur di­phenyl­phosphine and by a di­methyl­hydrazine, –C(H)=N—N(CH3)2, fragment. The two independent mol­ecules are linked by a C—H⋯N hydrogen bond. In the crystal, the A–B dimer is linked by a pair of C—H⋯S hydrogen bonds, forming a centrosymmetric four-mol­ecule arrangement. These units are linked by C—H⋯π inter­actions, forming a supra­molecular three-dimensional structure. PMID:29850039

Three closely related (2E,2′E)-3,3′-(1,4-phenyl­ene)bis­[1-(meth­oxy­phen­yl)prop-2-en-1-ones]: supra­molecular assemblies in one dimension mediated by hydrogen bonding and C—H⋯π inter­actions

PubMed Central

Chidan Kumar, C. S.; Then, Li Yee; Win, Yip-Foo; Quah, Ching Kheng; Naveen, S.; Chandraju, S.; Lokanath, N. K.; Warad, Ismail

2017-01-01

In the title compounds, (2E,2′E)-3,3′-(1,4-phenyl­ene)bis­[1-(2-meth­oxy­phen­yl)prop-2-en-1-one], C26H22O4 (I), (2E,2′E)-3,3′-(1,4-phenyl­ene)bis­[1-(3-meth­oxy­phen­yl)prop-2-en-1-one], C26H22O4 (II) and (2E,2′E)-3,3′-(1,4-phenyl­ene)bis­[1-(3,4-di­meth­oxy­phen­yl)prop-2-en-1-one], C28H26O6 (III), the asymmetric unit consists of a half-mol­ecule, completed by crystallographic inversion symmetry. The dihedral angles between the central and terminal benzene rings are 56.98 (8), 7.74 (7) and 7.73 (7)° for (I), (II) and (III), respectively. In the crystal of (I), mol­ecules are linked by pairs of C—H⋯π inter­actions into chains running parallel to [101]. The packing for (II) and (III), features inversion dimers linked by pairs of C—H⋯O hydrogen bonds, forming R 2 2(16) and R 2 2(14) ring motifs, respectively, as parts of [201] and [101] chains, respectively. PMID:28638654

A theoretical and shock tube kinetic study on hydrogen abstraction from phenyl formate.

PubMed

Ning, Hongbo; Liu, Dapeng; Wu, Junjun; Ma, Liuhao; Ren, Wei; Farooq, Aamir

2018-06-12

The hydrogen abstraction reactions of phenyl formate (PF) by different radicals (H/O(3P)/OH/HO2) were theoretically investigated. We calculated the reaction energetics for PF + H/O/OH using the composite method ROCBS-QB3//M06-2X/cc-pVTZ and that for PF + HO2 at the M06-2X/cc-pVTZ level of theory. The high-pressure limit rate constants were calculated using the transition state theory in conjunction with the 1-D hindered rotor approximation and tunneling correction. Three-parameter Arrhenius expressions of rate constants were provided over the temperature range of 500-2000 K. To validate the theoretical calculations, the overall rate constants of PF + OH → Products were measured in shock tube experiments at 968-1128 K and 1.16-1.25 atm using OH laser absorption. The predicted overall rate constants agree well with the shock tube data (within 15%) over the entire experimental conditions. Rate constant analysis indicates that the H-abstraction at the formic acid site dominates the PF consumption, whereas the contribution of H-abstractions at the aromatic ring increases with temperature. Additionally, comparisons of site-specific H-abstractions from PF with methyl formate, ethyl formate, benzene, and toluene were performed to understand the effects of the aromatic ring and side-chain substituent on H-abstraction rate constants.

Nuclear spatial delocalization silences electron density oscillations in 2-phenyl-ethyl-amine (PEA) and 2-phenylethyl-N,N-dimethylamine (PENNA) cations

DOE Office of Scientific and Technical Information (OSTI.GOV)

Jenkins, Andrew J.; Vacher, Morgane; Bearpark, Michael J.

2016-03-14

We simulate electron dynamics following ionization in 2-phenyl-ethyl-amine and 2-phenylethyl-N,N-dimethylamine as examples of systems where 3 coupled cationic states are involved. We study two nuclear effects on electron dynamics: (i) coupled electron-nuclear motion and (ii) nuclear spatial delocalization as a result of the zero-point energy in the neutral molecule. Within the Ehrenfest approximation, our calculations show that the coherent electron dynamics in these molecules is not lost as a result of coupled electron-nuclear motion. In contrast, as a result of nuclear spatial delocalization, dephasing of the oscillations occurs on a time scale of only a few fs, long before anymore » significant nuclear motion can occur. The results have been rationalized using a semi-quantitative model based upon the gradients of the potential energy surfaces.« less

Supramolecular engineering through temperature-induced chemical modification of 2H-tetraphenylporphyrin on Ag(111): flat phenyl conformation and possible dehydrogenation reactions.

PubMed

Di Santo, Giovanni; Blankenburg, Stephan; Castellarin-Cudia, Carla; Fanetti, Mattia; Borghetti, Patrizia; Sangaletti, Luigi; Floreano, Luca; Verdini, Alberto; Magnano, Elena; Bondino, Federica; Pignedoli, Carlo A; Nguyen, Manh-Thuong; Gaspari, Roberto; Passerone, Daniele; Goldoni, Andrea

2011-12-16

Scratching the surface: Formation of a monolayer of 2H-tetraphenylporphyrins (2H-TPP) on Ag(111), either by sublimation of a multilayer in the range 525-600 K or by annealing (at the same temperature) a monolayer deposited at room temperature, induces a chemical modification of the molecules. Rotation of the phenyl rings into a flat conformation is observed and tentatively explained, by using DFT calculations, as a peculiar reaction due to molecular dehydrogenation. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Ethyl 3-[1-(4-methoxy-phen-yl)-4-oxo-3-phenylazetidin-2-yl]-2-nitro-1-phenyl-2,3,10,10a-tetra-hydro-1H,5H-pyrrolo[1,2-b]isoquinoline-10a-carboxyl-ate.

PubMed

Sundaresan, S S; Ramesh, P; Arumugam, N; Raghunathan, R; Ponnuswamy, M N

2010-02-17

In the title mol-ecule, C(37)H(35)N(3)O(6), the pyrrolidine ring adopts a twist conformation and the piperidine ring is in a distorted boat conformation. One of the phenyl rings is disordered over two positions with occupancies of 0.54 (2) and 0.46 (2) and the ethyl carboxyl-ate group is also disordered over two orientations with occupancies of 0.75 (1) and 0.25 (1).

Chemical design of pH-sensitive nanovalves on the outer surface of mesoporous silicas for controlled storage and release of aromatic amino acid

DOE Office of Scientific and Technical Information (OSTI.GOV)

Roik, N.V., E-mail: roik_nadya@ukr.net; Belyakova, L.A.

2014-07-01

Mesoporous silicas with hexagonally arranged pore channels were synthesized in water–ethanol-ammonia solution using cetyltrimethylammonium bromide as template. Directed modification of silica surface with N-[N′-(N′-phenyl)-2-aminophenyl]-3-aminopropyl groups was realized by postsynthetic activation of halogenoalkylsilicas, which have surface uniformly or selectively distributed 3-chloropropyl groups, with 2-aminodiphenylamine in the liquid phase. Chemical composition of silica materials was estimated by IR spectroscopy and chemical analysis of the surface products of reactions. Characteristics of porous structure of MCM-41-type silicas were determined from X-ray and low-temperature nitrogen ad-desorption measurements. Release ability of synthesized silica carriers was established on encapsulation of 4-aminobenzoic acid in pore channels and subsequentmore » delivery at pH=6.86 and pH=1.00. It was found that N-[N′-(N′-phenyl)-2-aminophenyl]-3-aminopropyl groups block pore entrances at neutral pH preventing 4-aminobenzoic acid release. At pH=1.00 repulsion of positively charged surface aromatic amino groups localized near pore orifices provides unhindered liberation of aromatic amino acid from mesoporous channels. - Graphical abstract: Blocking of pores with N-[N′-(N′-phenyl)-2-aminophenyl]-3-aminopropyl groups at pH=6.86 for storage of ABA and opening of pore entrances at pH=1.00 for unhindered ABA liberation. - Highlights: • Modification of MCM-41 with N-[N′-(N′-phenyl)-2-aminophenyl]-3-aminopropyl groups. • Study of release ability of synthesized silica carriers in relation to amino acid. • Controlled blocking and opening of pores by amino groups at pH change were performed. • Retention of amino acid at pH=6.86 and its liberation at pH=1.00 was proved.« less

Synthesis and biological evaluation of 3-substituted-4-(4-methylthio phenyl)-1H-pyrrole derivatives as potential anticancer agents.

PubMed

Lan, Lan; Qin, Weixi; Zhan, Xiaoping; Liu, Zenglu; Mao, Zhenmin

2014-01-01

A novel series of 3-substituted-4-(4-methylthio phenyl)-1H-pyrrole derivatives were synthesized via Van Leusen pyrrole synthesis. The in vitro anticancer activity against a panel of 16 cancer cell lines and 2 normal cell lines was investigated by MTT assay. It was found that some of the pyrrole compounds showed similar antiproliferative activity against cancer cells compared with Paclitaxel, but little impact on normal cell lines, which indicated that the novel pyrrole derivatives could be used as potential anticancer candidates for possessing both selectivity and good therapeutic efficacy. Structure-activity relationship analysis found that 3-phenylacetyl-4- (4-methylthio phenyl)-1H-pyrrole derivatives displayed the most strong anticancer activity, among which [4-(4-methylthio phenyl)-1H-pyrrol- 3-yl] (4-methoxy phenyl) methanone (3j) was employed to investigate the effect of these pyrrole analogues on cell cycle by propidium iodide (PI) staining on cell flow cytometry. Cell necrotic effect of 10.0 µM 3j against MGC80-3 cells were also observed under fluorescence microscope and transmission electron microscope by ultrathin sections observation.

7-tert-Butyl-6-(4-chloro-phenyl)-2-thioxo-2,3-dihydro-1H-pyrido[2,3-d]pyrimidin-4-one, a classic polymodal inhibitor of transient receptor potential vanilloid type 1 with a reduced liability for hyperthermia, is analgesic and ameliorates visceral hypersensitivity.

PubMed

Nash, Mark S; McIntyre, Peter; Groarke, Alex; Lilley, Elliot; Culshaw, Andrew; Hallett, Allan; Panesar, Moh; Fox, Alyson; Bevan, Stuart

2012-08-01

The therapeutic potential of transient receptor potential vanilloid type 1 (TRPV1) antagonists for chronic pain has been recognized for more than a decade. However, preclinical and clinical data revealed that acute pharmacological blockade of TRPV1 perturbs thermoregulation, resulting in hyperthermia, which is a major hurdle for the clinical development of these drugs. Here, we describe the properties of 7-tert-butyl-6-(4-chloro-phenyl)-2-thioxo-2,3-dihydro-1H-pyrido[2,3-d]pyrimidin-4-one (BCTP), a TRPV1 antagonist with excellent analgesic properties that does not induce significant hyperthermia in rodents at doses providing maximal analgesia. BCTP is a classic polymodal inhibitor of TRPV1, blocking activation of the human channel by capsaicin and low pH with IC(50) values of 65.4 and 26.4 nM, respectively. Similar activity was observed with rat TRPV1, and the inhibition by BCTP was competitive and reversible. BCTP also blocked heat-induced activation of TRPV1. In rats, the inhibition of capsaicin-induced mechanical hyperalgesia was observed with a D(50) value of 2 mg/kg p.o. BCTP also reversed visceral hypersensitivity and somatic inflammatory pain, and using a model of neuropathic pain in TRPV1 null mice we confirmed that its analgesic properties were solely through the inhibition of TRPV1. We were surprised to find that BCTP administered orally induced only a maximal 0.6°C increase in core body temperature at the highest tested doses (30 and 100 mg/kg), contrasting markedly with N-[4-({6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl}oxy)-1,3-benzothiazol-2-yl]acetamide (AMG517), a clinically tested TRPV1 antagonist, which induced marked hyperthermia (>1°C) at doses eliciting submaximal reversal of capsaicin-induced hyperalgesia. The combined data indicate that TRPV1 antagonists with a classic polymodal inhibition profile can be identified where the analgesic action is separated from the effects on body temperature.

A novel (S)-(+)-decursin derivative, (S)-(+)-3-(3,4-dihydroxy-phenyl)-acrylic acid 2,2-dimethyl-8-oxo-3,4-dihydro-2H,8H-pyrano[3,2-g]chromen-3-yl-ester, inhibits ovalbumin-induced lung inflammation in a mouse model of asthma.

PubMed

Yang, Eun Ju; Song, Gyu-Yong; Lee, Ji-Sook; Yun, Chi-Young; Kim, In Sik

2009-03-01

(S)-(+)-Decursin is a coumarin compound present in herbal extracts that has various biological activities. (S)-(+)-Decursin attenuates pathophysiologic progression in cancer, bacterial infection and neuropathy. Asthma is an inflammatory disease associated with increased infiltration of leukocytes, especially eosinophils, and secretion of mucus into the airways. Although (S)-(+)-decursin, as well as (S)-(+)-decursin analogues, have various pharmacological properties, the effect of these compounds on asthma is not known. In the present study, we synthesized (S)-(+)-3-(3,4-dihydroxy-phenyl)-acrylic acid 2,2-dimethyl-8-oxo-3,4-dihydro-2H,8H-pyrano[3,2-g]chromen-3-yl-ester (compound 6, C6) from (S)-(+)-decursin and examined if C6 had any inhibitory effects on lung inflammation in a mouse model of ovalbumin-induced asthma. C6 significantly inhibited the leukocytosis (p < 0.01) and eosinophilia (p < 0.05) in bronchoalveolar lavage (BAL) fluid. Examination of lung tissues stained with hematoxylin and eosin and periodic acid Schiff reagents showed that C6 suppressed the increased infiltration of inflammatory cells and elevated mucus hypersecretion. Protein levels of interleukin (IL)-5 (p < 0.05) and eotaxin (p < 0.01) were significantly reduced in BAL fluid by C6. C6 also significantly reduced total and ovalbumin-specific immunoglobulin E (IgE) levels in BAL fluid (p < 0.01) as well as that in serum (p < 0.05). C6 may have pharmacological effects for asthma and may be a potent therapeutic agent for the treatment of allergic airway diseases.

A Study of the Curing and Flammability Properties of Bisphenol A Epoxy Diacrylate Resin Utilizing a Novel Flame Retardant Monomer, bis[di-acryloyloxyethyl]-p-tert-butyl-phenyl Phosphate

PubMed Central

Rwei, Syang-Peng; Chen, Yu-Ming; Chiang, Whe-Yi; Ting, Yi-Tien

2017-01-01

A UV-curable, flame-retardant monomer, DAPP (bis[di-acryloyloxyethyl]-p-tert-butyl-phenyl-phosphate), was synthesized based on BPDCP (4-tert-butylphenyl-dichloro phosphate) and HEA (2-hydroxy ethyl acrylate). DAPP was blended with regular bisphenol A epoxy acrylate (BAEA) in various ratios to yield various phosphorus contents. The TGA-IR (thermogravimetric analyzer interface with an infrared spectrometer) results demonstrate that compounding 30 mol % DAPP with BAEA significantly reduced the amount of released CO gas. In contrast, the peak intensity of CO2 is independent of phosphorus content. The limiting oxygen index (LOI), reaching the saturated value of 26, and the heat release rate (HRR) measured using a cone-calorimeter, 156.43 KW/m2, confirm the saturation point when 30 mol % DAPP was compounded into BAEA. A study of the kinetics of pyrolysis reveals that Ea decreases as the phosphorus content increases. Both the TGA-IR and pyrolysis results reveal that the phosphorus compound DAPP is easily decomposed during the initial stage of burning to form an insulating layer, which inhibits further burning of the resin and the consequent release of other flammable gases. PMID:28772562

The new generation dihydropyridine type calcium blockers, bearing 4-phenyl oxypropanolamine, display alpha-/beta-adrenoceptor antagonist and long-acting antihypertensive activities.

PubMed

Liang, Jhy-Chong; Yeh, Jwu-Lai; Wang, Chia-Sui; Liou, Shwu-Fen; Tsai, Chieh-Ho; Chen, Ing-Jun

2002-03-01

A new series of dihydropyridine derivatives, bearing oxypropanolamine moiety on phenyl ring at the 4-position of the dihydropyridine base, were prepared. Oxypropanolamine was synthesized by replacing the phenolic OH of vanillin or other compounds, having a phenyl aldehyde group, with epichlorohydrin, followed by cleavaging the obtained epoxide compounds with tert-butylamine, n-butylamine or 2-methoxy-1-oxyethylamino benzene (guaiacoxyethylamine), respectively. Obtained various oxypropanolamine compounds, still remaining a phenyl aldehyde moiety, were then performed by Hantzsch condensation reaction with methylacetoacetate or ethylacetoacetate, respectively, to give our new series of dihydropyridine linked with the 4-phenyl ring. These compounds were evaluated for inotropic, chronotropic, and aorta contractility that associated with calcium channel and adrenoceptor antagonist activities. Dihydropyridine derivatives that with oxypropanolamine side chain on their 4-phenyl ring associated alpha-/beta-adrenoceptor blocking activities created a new family of calcium entry and the third generation beta-adrenoceptor blockers. Optimizing this research to obtain more potent alpha-/beta-adrenoceptor blocking and long-acting antihypertensive oxypropanolamine on the 4-phenyl ring of dihydropyridine series compounds was thus accomplished and classified as third generation dihydropyridine type calcium channel blockers, in comparison with previous short-acting type nifedipine and long-acting type amlodipine. We concluded that compounds 1a, 1b and 1g showed not only markedly high calcium-antagonistic activity but also the highest antihypertensive effect; compounds 1b, 1c, 1f, 1g, 1i and 1j induced sustained antihypertensive effects are major and attributed to their calcium entry and alpha-adrenoceptor blocking activities in the blood vessel due to their introduction of 2-methoxy, 1-oxyethylamino benzene moiety in the side chain on the 4-phenyl ring of dihydropyridine. Bradycardiac