Synthesis and Biological Activity of 4-(4-Hydroxybenzylidene)-2- (substituted styryl) oxazol-5-ones and Their o-glucosides

Authors

VIJAY TAILE
KISHOR HATZADE
PRAVIN GAIDHANE
VISHWAS INGLE

Abstract

The 4-(4-hydroxybenzylidene)-2-methyl oxazol-5-ones 1 were treated with various aldehydes in the presence of acetic acid to form 4-(4-hydroxybenzylidene)-2-(substituted styryl) oxazol-5-ones 2a-i, which were glucosylated using \alpha-acetobromoglucose as a glucosyl donor to afford 4-(4-o-\beta-d-tetra-o-acetyl-glucoxybenzylidene)-2- (substituted styryl) oxazol-5-ones 3a-i, which were deacetylated using zinc acetate in absolute methanol to form 4-(4-o-\beta-d-glucoxybenzylidene)- 2-(substituted styryl) oxazol-5-ones 4a-i. The compounds showed good antimicrobial and antifungal activity.

DOI

10.3906/kim-0712-12

Keywords

Oxazolone, \alpha -acetobromoglucose, decetylation, o-glucosides, antimicrobial and antifungal activity

First Page

295

Last Page

305

Recommended Citation

TAILE, V, HATZADE, K, GAIDHANE, P, & INGLE, V (2009). Synthesis and Biological Activity of 4-(4-Hydroxybenzylidene)-2- (substituted styryl) oxazol-5-ones and Their o-glucosides. Turkish Journal of Chemistry 33 (2): 295-305. https://doi.org/10.3906/kim-0712-12