Abstract

SYNTHESIS, ANTIMICROBIAL AND ANTI-INFLAMMATORY ACTIVITY OF NEW (E)-3-(3-METHYL-5-STYRYLISOXAZOL-4-YL)-10-PHENYL-3,9,10,10A-TETRAHYDRO-2H-BENZO[B]THIAZOLO[4,5-E][1,4]DIAZEPINE-2-THIONES

Modugu Nagi Reddy*, Pittala Praveen Kumar, Eligeti Rajanarendar, Y. N. Reddy

ABSTRACT

A novel series of isoxazolyl thiazolobenzodiazepine-2-thiones 6 have been synthesized from 4-amino-3-methyl-5-styrylisoxazoles 1. Compounds 1 on treatment with bis(carboxymethyl)trithiocarbonate 2 afforded the corresponding isoxazolyl thioxothiazolidin-4-ones 3 under microwave irradiation. The Knoevenagel condensation of compounds 3 with aromatic aldehydes to give compounds 4. Compounds 4, on treatment with o-phenylenediamine 5 in refluxing xylene underwent cyclization to give the title compounds 6. Structures of compounds 3, 4 and 6 were established on the basis of IR, 1H NMR, 13C NMR and mass spectral data. The title compounds 6a-n were evaluated for their antimicrobial and anti-inflammatory activities. Compounds 6m and 6n exhibited significant antimicrobial and potent anti-inflammatory activities as that of standard drugs.

Keywords: Isoxazolyl thiazolobenzodiazepine-2-thiones, Knoevenagel condensation, antimicrobial activity, anti-inflammatory activity.