Synthesis, spectroscopic, crystal structure and in vitro cytotoxicity studies of N-thiophenoyl-N′-substituted phenyl thiocarbamide derivatives

A series of eight biologically active N, N'-disubstituted thiocarbamide compounds (1-8) have been prepared from thiophene-2-carbonyl isothiocyanate and various substituted aromatic primary amines (2,4-dichlorophenyl aniline, 4-chloro-3-nitrophenyl aniline, 4-methoxycarbonylphenyl aniline, 3-methoxycarbonylphenyl aniline, 2-methoxycarbonylphenyl aniline, 4-methoxyphenyl aniline, 2-methoxyphenyl aniline and 2-nitrophenyl aniline). Their structures were confirmed by elemental analyses, various spectroscopic techniques ((FT-IR, H-1 and C-13 NMR) and single crystal X-ray analysis of compound (1). In the molecular structure of compound (1) twisted confirmation of the carbonyl and thiocarbonyl group across C-N bond of thiocarbamide moiety and an offset face-to-face pi-pi stacking between two thiophene and two benzene ring of two molecules is observed. In vitro cytotoxicity assay of all the above compounds and five more (9-13) were carried out using seven human cancer cell lines; cervical (2008 and C13*), colorectal (HT29 and HCT116) and ovarian carcinoma (A2780, A2780/CP and IGROV-1). The results revealed that compounds 1, 11, 12 and 13 displayed promising inhibitory activity against all the cell lines tested. (C) 2018 Elsevier B.V. All rights reserved.