SYNTHESIS, REACTIONS, AND ANTI-BACTERIAL ACTIVITY OF SOME NEW N-BENZYL-4-OXOTHIAZOLIDIN-2-YLIDENE)ACETAMIDE DERIVATIVES

doi:10.21608/absb.2009.7654

SYNTHESIS, REACTIONS, AND ANTI-BACTERIAL ACTIVITY OF SOME NEW N-BENZYL-4-OXOTHIAZOLIDIN-2-YLIDENE)ACETAMIDE DERIVATIVES

Document Type : Original Article

10.21608/absb.2009.7654

Abstract

Treatment of N-benzyl-2-cyanoacetamide (1) with ethyl isothiocyanate (2) and p-phenylenediisothiocyanate (11) gave the non-isolable intermediates 3 and 12, respectively. Subsequent treatment of 3 and 12, respectively with α-halo esters and/or chloroacetone gave the corresponding 4-oxothiazolidin-2-ylidene 5a-c, bis(4-oxothiazolidin-2-ylidene) (14), thiazol-2-ylidene (6) and bis(5-acetyl-4-amino-3-N-benzylthiophenecarboxamido)-1-,4-pheneylenediamine (13) derivatives, respectively. Reaction of 5a with electrophilic carbon was studied where derivatives (8a,b), 10 were obtained. Cyclocondensation of 1 with thioglycolic acid afforded thiazolidin-4-one derivative (15). Condensation of 15 with 1-naphthaldehyde, arylidenemalononitriles and ethyl α-cyanocinnamate gave 4,5-dihydro-thiazol-2-ylacrylamide (17), thiazolo[3,2-a]pyridines (16a,b) and (18), respectively. The structures of these new compounds were confirmed by IR, (¹H- and ¹³C-NMR) and mass spectral analyses. Some of the synthesized compounds were tested in vitro for their antimicrobial activity, where compounds 5a, 6, 8b, 16a, 16b, and 17 exhibited the best anti-bacterial activity against Salmonella typhi NCIM130331.

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