Structural Determination, And biological activity of New

91109

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

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-a-dglucopyranosyl bromide afforded 2, 3, 4, 6-tetra-o-acetyl-b-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-b-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.
Anahtar Kelimeler:

Chromones, pyrazoles, glucopyranosyl bromide, glucosylation, o-b-d-glucosides.

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

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-a-dglucopyranosyl bromide afforded 2, 3, 4, 6-tetra-o-acetyl-b-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-b-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-b-d-glucosides.,

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Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Arşiv
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