Vijay TAILE, Kishor HATZADE, Pravin Gaidhane And Vishwas INGLE

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

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 a-acetobromoglucose as a glucosyl donor to afford 4-(4-o-b-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-b-d-glucoxybenzylidene)- 2-(substituted styryl) oxazol-5-ones 4a-i. The compounds showed good antimicrobial and antifungal activity.

Anahtar Kelimeler:

Oxazolone, a -acetobromoglucose, decetylation, o-glucosides, antimicrobial and antifungal activity

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

Keywords:

Oxazolone, a -acetobromoglucose, decetylation, o-glucosides, antimicrobial and antifungal activity,

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(4-o-β -d-glucoxybenzylidene)-2-(3-nitro styryl) oxazol-5-ones (4h). Yield 72%; [ α ]30=-15.10 D
(4-o-β -d-glucoxybenzylidene)-2-(4-dimethyamino styryl) oxazol-5-ones (4i).
Yield 60%; [ α ]30=-18.65 (c 0.1, DMSO); FT-IR (KBr) cm−1: 3385 (intramolecular –OH, broad, carbohydrate group), D