Preparations of 5-Alkylmethylidene-3-carboxymethylrhodanine Derivatives and Their Aldose Reductase Inhibitory Activity

Yoshitaka OHISHI; Teruo MUKAI; Michiko NAGAHARA; Motoyuki YAJIMA; Norio KAJIKAWA; Kazumoto MIYAHARA; Tsunehiro TAKANO

doi:10.1248/cpb.38.1911

Yoshitaka OHISHI, Teruo MUKAI, Michiko NAGAHARA, Motoyuki YAJIMA, Norio KAJIKAWA, Kazumoto MIYAHARA, Tsunehiro TAKANO

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Keywords: 5-monoalkylmethylidene-3-carboxymethylrhodanine, 5-dialkylmethylidene-3-carboxymethylrhodanine, 5-alkylaminomethylidene-3-carboxymethylrhodanine, stereoselectivity, configuration, X-ray structure analysis, aldose reductase, enzyme inhibitory potency

JOURNAL FREE ACCESS

1990 Volume 38 Issue 7 Pages 1911-1919

DOI https://doi.org/10.1248/cpb.38.1911

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Abstract

Reactions of 3-carboxymethylrhodanine (1) with aldehydes (2a-u) afforded stereoselectively the 5-monoalkymethylidene-3-carboxymethylrhodanines (3a-u). The configuration of the 5-monoalkylmethylidene-3-carboxymethylrhodanine (3k) were examined by X-ray structure analysis and confirmed to be Z-configuration. The stereoselective reaction path was discussed. Several 5-dialkylmethylidene-3-carboxymethylrhodanines (15a-f) and alkyl-amino derivatives of 3-carboxymethylrhodanines (18a-o) were also prepared.These products were evaluated for aldose reductase-inhibitory potency and half of them exhibited valuable inhibitory potency.

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