Abstract

DESIGN AND SYNTHESIS OF NEW (E)-2-((3-METHYL-5-STYRYL- ISOXAZOL-4-YL) AMINO)-N-(4-OXO-2-PHENYLTHIAZOLIDIN-3-YL)- ACETAMIDE DERIVATIVES AS POTENTIAL ANTIMICROBIAL AGENTS

D. Karunakar*, T. Suvarna, Y. N. Reddy and M. Nagi Reddy

ABSTRACT

A series of new (E)-2-((3-methyl-5-styrylisoxazol-4-yl)amino)-N-(4-oxo-2-phenyl- thiazolidin-3-yl)acetamides 5 have been synthesized from (E)-ethyl-2-((3-methyl-5-styrylisoxazol-4-yl)amino)acetates synthon 2. Compound 2 was obtained by reaction of 4-amino-3-methyl 5-styrylisoxazoles 1 with ethyl bromoacetate. Compound 2 on treatment with hydrazine hydrate yields (E)-2-((3-methyl-5-styrylisoxazol-4-yl) amino) acetohydrazides 3. The condensation of compound 3 with different aromatic aldehydes afforded a series of N'-benzylidene-2-((3-methyl-5-((E)-styryl) isoxazol-4-yl) amino) acetohydrazide Schiff' s bases 4. Cyclo condensation of compounds 4 with 2-mecrcapto acetic acid in dry benzene affords (E)-2-((3-methyl-5-styrylisoxazol-4-yl) amino)-N-(4-oxo-2-phenylthiazolidin-3-yl) acetamides 5. Compounds 2-5 were characterized by IR, 1H NMR, 13C NMR, and mass spectral data. The title compounds 5a-i were evaluated for their antimicrobial activity. The results showed that these compounds showed good antibacterial and antifungal activity compared with that of standard antibiotics.

Keywords: Isoxazolyl thiazolidinone acetamide, antibacterial, antifungal activity.