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

A series of eight biologically active N, N0-disubstituted thiocarbamide compounds (1e8) 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 ((FTeIR, 1H and 13C 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 CeN bond of thiocarbamide moiety and an offset face-to-face pep 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 (9e13) 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.