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, α-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, 1H NMR, 13C 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. © 2013 The Japan Institute of Heterocyclic Chemistry.