- Synthesis, crystal structure, and spectroscopic and electronic properties of N-[4-(3-Methyl-3-Phenyl-Cyclobutyl)-Thiazol-2-yl]-N'-phenyl hydrazine
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The title molecule, N-[4-(3-Methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-N'- phenyl hydrazine (C20H21N3S), was prepared and characterized by elemental analysis, 1H-NMR, 13C-NMR, FT-IR, UV-Visible (UV-Vis), and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P21/c with a = 12.2960(5), b = 13.9565(5), c = 10.6356(5) A, and β= 99.106(3). Molecular geometries from X-ray experiment, vibrational frequencies, atomic charges distribution, dipole moments and total energies of the title compound and the dimer in the ground state have been calculated using the density functional theory method (RB3LYP) with 6-31G(d, p) and 6-311G(d, p) basis sets, and compared with the experimental data. Calculated results show that DFT at the RB3LYP/6-31G(d, p) and 6-311G(d, p) levels can well reproduce the structure of the title compound. To determine conformational flexibility, the molecular energy profile of the title compound was obtained by semi-empirical (RAM1) calculations with respect to the selected torsion angle, which was varied from-180 to +180 in steps of 10. In addition, the molecular electrostatic potential (MEP), frontier molecular orbitals, thermodynamic properties, and UV-Vis absorption spectra of the title compound were investigated using theoretical calculations. UV-Vis absorption spectra of the compound have been ascribed to their corresponding molecular structure and electrons orbital transitions. Copyright Taylor & Francis Group, LLC.
- Saracoglu,Guentepe,Yueksektepe,Caliskan,Cukurovali
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- Synthesis and antitumor effects of a new class of 1,2,4-triazole derivatives
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In order to obtain more effective antitumor agents, a new class of 1,2,4-triazole derivatives bearing disulfide bond were designed and synthesized. All the final compounds were confirmed by IR, 1H NMR, 13C NMR and HR-ESI-MS. The in vitro cytotoxicity of the compounds on the SMMC-7721, Hela, A549 cancer cell lines and the L929 normal cell lines were assessed by cell counting kit-8 (CCK-8). Many of tested compounds 8a–h, 9a–h, 10a–h had better cytotoxic activity on various cancer cell lines than positive control 5-fluorouracil, and they were less cytotoxic to normal cell line L929 than cancer cells. Among them, compounds 9e, 9g, and 10h showed better cytotoxic activity on SMMC-7721 cells with IC50 values 4.12, 2.92, and 4.53 μM, respectively. Compounds 8a, 9g, 10g and 10h displayed high antiproliferative activity against Hela cells with IC50 values 6.31, 4.31, 6.31 and 3.97 μM, respectively. Compounds 8c, 10a and 10h revealed effective biological potency on A549 cells with IC50 values 4.75, 4.92 and 3.73 μM, respectively. Moreover, a great majority of tested compounds revealed low cytotoxicity on normal cell line L929.
- Wu, Zheng,Li, Xin,Chi, Chun-Lan,Xu, Lu,Sun, Yong-Yue,Chen, Bao-Quan
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p. 142 - 151
(2020/10/22)
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- Discovery of novel hybrids of diaryl-1,2,4-triazoles and caffeic acid as dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase for cancer therapy
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Inflammation plays a key role in cancer initiation and propagation. Cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX), two important enzymes in inflammatory responses are up-regulated in various tumor types. Dual inhibition of COX-2 and 5-LOX constitutes a rational concept for the design of more efficacious anti-tumor agents with an improved safety profile. We have previously reported a series of diaryl-1,2,4-triazole derivatives as selective COX-2 inhibitors. Herein, we hybridized the diaryl-1,2,4-triazoles with caffeic acid (CA) which was reported to display 5-LOX inhibitory and anti-tumor activities, affording a novel class of COX-2/5-LOX dual inhibitors as anti-tumor drug candidates. Most of these compounds exhibited potent COX-2/5-LOX inhibitory and antiproliferative activities in vitro. And the most potent compound 22b could significantly inhibit tumor growth in vivo. Furthermore, mechanistic investigation showed that the representative compound 15c blocked cell cycle in G2 phase and induced apoptosis in human non-small cell lung cancer A549 cells in a dose-dependent manner. Our preliminary investigation results would provide new clues for the cancer theatment with COX-2/5-LOX dual inhibitors.
- Cai, Hao,Huang, Xiaojing,Xu, Shengtao,Shen, Hao,Zhang, Pengfei,Huang, Yue,Jiang, Jieyun,Sun, Yijun,Jiang, Bo,Wu, Xiaoming,Yao, Hequan,Xu, Jingyi
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- Discovery of potential anti-inflammatory drugs: Diaryl-1,2,4-triazoles bearing N-hydroxyurea moiety as dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase
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A series of hybrids from diaryl-1,2,4-triazole and hydroxamic acid or N-hydroxyurea were synthesized and evaluated as novel anti-inflammatory agents. The biological data showed that (i) all the compounds showed dual COX-2/5-LOX inhibitory activities in vitro, and 15e showed optimal inhibitory activities (COX-2: IC50 = 0.15 μM, 5-LOX: IC50 = 0.85 μM), (ii) 15e selectively inhibited COX-2 relative to COX-1 with selectivity index (SI = 0.012) comparable to celecoxib (SI = 0.015), (iii) 15e exhibited potent anti-inflammatory activity (inhibition: 54.1%) which was comparable to the reference drug celecoxib (inhibition: 46.7%) in a xylene-induced ear edema assay, and (iv) 15e displayed promising analgesic activity in acetic acid-induced writhing response and hot-plate assay. Finally, a molecular modeling study revealed the binding interactions of 15e with COX-2 and 5-LOX. Our findings suggest that 15e may be a promising anti-inflammatory agent for further evaluation.
- Jiang, Bo,Huang, Xiaojing,Yao, Hequan,Jiang, Jieyun,Wu, Xiaoming,Jiang, Siyi,Wang, Qiujuan,Lu, Tao,Xu, Jinyi
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p. 2114 - 2127
(2014/03/21)
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- Synthesis of mono- and N,N-disubstituted thioureas and N-acylthioureas
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1-Benzotriazole-1-carbothioamide (2), prepared from 1-cyanobenzotriazole (1) and hydrogen sulfide, reacts with amines to give thioureas 3a-e. Reactions of (benzotriazol-1-yl)carboximidamides 4a-d,f-j and acyl- 5a-f,i-k or arylaminocarbonyl- 5g,h (benzotri
- Katritzky, Alan R.,Kirichenko, Nataliya,Rogovoy, Boris V.,Kister, Jeremy,Tao, Hui
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p. 1799 - 1805
(2007/10/03)
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- [5,5] sigmatropic shift of N-phenyl-N'-(2-thiazolyl)hydrazines and N,N'- bis(2-thiazolyl)hydrazines into 2-amino-5-(p-aminophenyl)thiazoles and 5,5'- bis(2-aminothiazole) derivatives
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[5,5] Sigmatropic shift of N-phenyl-N'-(2-thiazolyl)hydrazines and N,N'- bis(2-thiazolyl)hydrazines in acid-catalyzed benzidine-type rearrangement into 2-amino-5-(p-aminophenyl)thiazoles and 5,5'-bis(2-aminothiazole) derivatives is described, respectively. (C) 2000 Elsevier Science Ltd.
- Lee, Boong Won,Lee, Seung Dal
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p. 3883 - 3886
(2007/10/03)
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- INVESTIGATIONS IN THE SERIES OF DITHIOCARBAMIC ACID DERIVATIVES. IX. ARYLHYDRAZINOTHIOCARBONYLATION OF COMPOUNDS CONTAINING AN ACTIVE HYDROGEN ATOM
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The reaction of methyl phenyldithiocarbazate with ethyl cyanoacetate, cyanoacetamide, acetylacetone, and malonic ester leads to the formation of 1,4,5-trisubstituted pyrazoline-3-thiones.The reaction of methyl phenyldithiocarbazate with arylamines and arylhydrazines gave the respective derivatives of thiosemicarbazide and thiocarbohydrazide.
- Bazavova, I. M.,Dubenko, R. G.,Pel'kis, P. S.
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p. 189 - 193
(2007/10/02)
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- Substituent effects on the spectral behavior and synthesis of mercury 1,5-diarylthiocarbazonates
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Symmetric and unsymmetric substituted 1,5-diarylthiocarbazones, and their mono- and bismercury complexes, were synthesized for spectral analysis.The first singlet-singlet transition of the mercury complexes was determined and the spectral shift produced by trifluoromethyl substitution was compared with that caused by different substituents in similar complexes.The large magnitude of the hypsochromic shift produced by the trifluoromethyl substituent can be explained by concerted steric and inductive effects, while the smaller bathochromic shift induced by the methoxy substituent is a result of opposing steric and electronic effects.In the trifluoromethyl substitution, a hypsochromic shift caused by steric influences was found to be 500 cm-1 in the photochromic unactivated state, and 250 cm-1 in the photochromic activated state.A similar shift caused by inductive influences was found to be 750 cm-1 in the photochromic unactivated state, and 600 cm-1 in the photochromic activated state.The smaller spectral shift observed in the photochromic activated state is consistent with the elucidated structure of the unsymmetric 1,5-diarylthiocarbazone, 6d, which was shown that the trifluoromethyl substitution was on the phenylazo portion of the molecule by chemical and spectral studies.
- Chu, Nori Y. C.,Goldstein, Steven A.,Keehn, Philip M.
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p. 679 - 687
(2007/10/02)
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