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Synthesis and biological evaluation of several 3-(coumarin-4-yl)tetrahydroisoxazole and 3-(coumarin-4-yl)dihydropyrazole derivatives

✍ Scribed by Anne A. Emmanuel-Giota; Konstantina C. Fylaktakidou; Konstantinos E. Litinas; Demetrios N. Nicolaides; Dimitra J. Hadjipavlou-Litina

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
63 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A series of novel 3‐(coumarin‐4‐yl)tetrahydroisoxazoles 5a,b, 7, 9 and 3‐(coumarin‐4‐yl)dihydropyra‐zoles 13a‐d, 14,15a,b were synthesized from coumarin‐4‐carboxaldehyde 1 via the intermediate N‐methyl nitrone 3 and N‐phenyl or N‐methyl hydrazones 11a,b. These coumarin derivatives were isolated, characterized and evaluated in vitro for their ability to inhibit trypsin, β‐glucuronidase, soybean lipoxygenase and to interact with the stable radical 1,1‐diphenyl‐2‐picrylhydrazyl. The compounds were tested in vivo as anti‐inflammatory agents in the rat carrageenin paw edema assay. Compound 15a seems to be a lead molecule to be modified in order to improve the lipoxygenase inhibition. The results are discussed in terms of structural characteristics.

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