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

A series of new spiro[cyclopropane‐1,4′‐pyrazol‐3‐one] derivatives 3a‐h were synthesized by the reaction of 4‐arylidene‐3H‐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 chloro...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2008-11, Vol.45 (6), p.1883-1887
Main Authors: Maruoka, Hiroshi, Kashige, Nobuhiro, Eishima, Takafumi, Okabe, Fumi, Fujioka, Toshihiro, Miake, Fumio, Yamagata, Kenji, Tanaka, Reiko
Format: Article
Language:English
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Summary:A series of new spiro[cyclopropane‐1,4′‐pyrazol‐3‐one] derivatives 3a‐h were synthesized by the reaction of 4‐arylidene‐3H‐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.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570450653