645-48-7Relevant articles and documents
Synthesis, crystal structure, and spectroscopic and electronic properties of N-[4-(3-Methyl-3-Phenyl-Cyclobutyl)-Thiazol-2-yl]-N'-phenyl hydrazine
Saracoglu,Guentepe,Yueksektepe,Caliskan,Cukurovali
, p. 237 - 255 (2011)
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.
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
Cai, Hao,Huang, Xiaojing,Xu, Shengtao,Shen, Hao,Zhang, Pengfei,Huang, Yue,Jiang, Jieyun,Sun, Yijun,Jiang, Bo,Wu, Xiaoming,Yao, Hequan,Xu, Jingyi
, p. 89 - 103 (2015/12/04)
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.
Synthesis of mono- and N,N-disubstituted thioureas and N-acylthioureas
Katritzky, Alan R.,Kirichenko, Nataliya,Rogovoy, Boris V.,Kister, Jeremy,Tao, Hui
, p. 1799 - 1805 (2007/10/03)
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
