Synthesis, structural determination, and biological activity of new 7-hydroxy-3-pyrazolyl-4H-chromen- 4-ones and their o-\beta-D-glucosides

Authors

KISHOR HATZADE
VIJAY TAILE
PRAVIN GAIDHANE
VISHWAS INGLE

DOI

10.3906/kim-0902-11

Abstract

A convenient route to synthesize some new medicinally important 7-hydroxy-3-pyrazolyl chromones (3a-i) is described. The interaction of 7-hydroxy-3-formyl chromone (1) with various substituted acetophenones and further cyclization with hydrazine hydrate in an aprotic solvent followed by condensation with 2, 3, 4, 6-tetra-o-acetyl-\alpha-dglucopyranosyl bromide afforded 2, 3, 4, 6-tetra-o-acetyl-\beta-d-glucopyranosyloxy-3-(3-aryl-1H-pyrazol-5- yl)-4H-chromen-4-ones (4a-i). Later deacetylation with anhydrous zinc acetate in methanol gave 7-o-\beta-d-glucopyranosyloxy-3-(3-aryl- 1H-pyrazol-5-yl)-4H-chromen-4-ones (5a-i). These compounds were evaluated for their in vitro antimicrobial and anti-oxidant activity. The structures of these newly synthesized o-glucosides were established by IR, NMR, mass spectra, elemental analysis, and chemical analysis.

Keywords

Chromones, pyrazoles, glucopyranosyl bromide, glucosylation, o-\beta-d-glucosides.

First Page

241

Last Page

254

Recommended Citation

HATZADE, KISHOR; TAILE, VIJAY; GAIDHANE, PRAVIN; and INGLE, VISHWAS (2010) "Synthesis, structural determination, and biological activity of new 7-hydroxy-3-pyrazolyl-4H-chromen- 4-ones and their o-\beta-D-glucosides," Turkish Journal of Chemistry: Vol. 34: No. 2, Article 9. https://doi.org/10.3906/kim-0902-11
Available at: https://journals.tubitak.gov.tr/chem/vol34/iss2/9