Synthetic Utility of Ethylidenethiosemicarbazide: Synthesis and Anticancer Activity of 1,3-Thiazines and Thiazoles with Imidazole Moiety

Abstract

Reactions of ethylidenethiosemicarbazide 3 with DMAD 4 or substituted methylenemalononitriles 8 gave thiazolidin-4-one 6 or 1,3-thiazine derivatives (10, 11), respectively.Also, treatment of 3 with hydrazonoyl halides 12a-i, -haloketones 15a-d, and chloroacetic acid 18 afforded the corresponding arylazothiazoles 14a-i, thiazoles 17a-d, and thiazolin-4-one derivative 20, respectively.The structures of the synthesized products were confirmed by IR, 1 H NMR, 13 C NMR and mass spectral techniques.The anticancer activity of the selected products against the colon carcinoma cell line (HCT-116) was determined and the results revealed promising activity of compound 6.