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Synthesis and antifungal activity of spiro[cyclopropane-1,4′-pyrazol-3-one] derivatives

✍ Scribed by Hiroshi Maruoka; Nobuhiro Kashige; Takafumi Eishima; Fumi Okabe; Toshihiro Fujioka; Fumio Miake; Kenji Yamagata; Reiko Tanaka

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
236 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A series of new spiro[cyclopropane‐1,4′‐pyrazol‐3‐one] derivatives 3a‐h were synthesized by the reaction of 4‐arylidene‐3__H__‐pyrazol‐3‐one 1 with secondary and tertiary carbanions derived from a methylene and methine group bearing both a leaving group and electron‐withdrawing group, e.g. methyl chloroacetate, ethyl chloroacetate, isopropyl chloroacetate, tert‐butyl chloroacetate, chloroacetonitrile, 2‐chloro‐N,N‐diethylacetamide, methyl 2‐chloropropionate and 2‐chloropropionitrile, in the presence of sodium hydride. All the synthesized compounds 3a‐h were active against Candida albicans with MIC ≤ 25 μg/mL in vitro.

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