ABSTRACT
New N-substituted amides of 3-(3-ethylthio-1,2,4-triazol-5-yl)propenoic acid (2-12) were designed and prepared by the condensation reaction of exo-S-ethyl-7-oxabicyclo-[2.2.1]-hept-5-ene-2,3-dicarbonyl isothiosemicarbazide (1) with primary amines. The chemical structure of all compounds was confirmed by IR, (1)H NMR, (13)C NMR spectra, the X-ray crystallography (for compounds 8, 11, 12) and elemental analysis. Moreover, compounds 9-11 were screened for their anticancer activity. Compounds 9 (in concentrations of 0.32 mM and 0.16 mM), 10 (in concentrations of 0.28 mM and 0.14 mM), and 11 (in concentrations of 0.35 mM and 0.17 mM) were found to be evidently effective in vitro against lung cell line (IC50). The distinctly marked antiproliferative effect of compounds 9 and 10 in breast carcinoma cells in vitro was ascertained. Moreover, the lowest cytotoxicity of compound 9 in concentrations of 0.16 mM and 0.03 mM against the normal skin fibroblast cell line and breast carcinoma cell in vitro after 24- and 48-h periods of incubation was noticed in this study.
Subject(s)
Amides/chemistry , Amides/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Triazoles/chemistry , Triazoles/pharmacology , Amides/chemical synthesis , Antineoplastic Agents/chemical synthesis , Breast Neoplasms/drug therapy , Carcinoma/drug therapy , Cell Line , Cell Line, Tumor , Cell Proliferation/drug effects , Crystallography, X-Ray , Female , Fibroblasts/cytology , Humans , Lung Neoplasms/drug therapy , Skin/cytology , Triazoles/chemical synthesisABSTRACT
The title compound, C(9)H(11)N(3)S(2), exists in the thione form in the crystal structure. The central triazole ring is almost perpendicular to the thio-phene ring which is disordered over two orientations [dihedral angles of 88.5â (7) and 85.7â (8)° for the two orientations]. The crystal structure is stabilized by strong inter-molecular N-Hâ¯S hydrogen bonds, forming centrosymmetric dimers, and by some weak C-Hâ¯S inter-actions.
