Synthesis, antioxidant and antimicrobial evaluation of thiazolidinone, azetidinone encompassing indolylthienopyrimidines

Abstract

Various 2-amino-N′-{3-(2′,5′-disubstituted-1H-indol- 3′-yl)methylene}-4,5-dimethylthieno-3- carbohydrazides (3) synthesized by condensation of 2-amino-4,5-dimethyl thiophene-3-carbohydrazide (2) with 2,5- disubstituded indole-3-carboxaldehyde (1). The Schiff's base (3) on cyclocondensation with acetic anhydride and triethyl orthoformate afforded thienopyrimidine analogues (4) and (7), respectively. Compounds 4 or 7 on cyclization with thioglycolic acid and chloroacetyl chloride gave thiazolidin-4-ones (5) or (8) and azitidin-2-ones (6) or (9) respectively. The structures of these newly synthesized compounds have been established on the basis of their spectral data and elemental analysis. Some of the compounds exhibited promising antioxidant and antimicrobial activities. [Figure not available: see fulltext.] © 2011 Indian Academy of Sciences.