Preparation of 5-alkyl-3-carboxymethylrhodanines and their aldose reductase inhibitory activity.
5-Alkyl-3-carboxymethylrhodanines (2) were prepared from 5-alkylmethylidene-3-carboxymethylrhodanines (1). The exo double bond of 1 was successfully reduced with NaBH4. The 1,4-addition reaction path was confirmed on the basis of proton nuclear magnetic resonance spectrum of the product (4b) obtained from the reduction of 3 using NaBD4. Optical resolution of the tert-butyl compound (2i) was achieved upon epimerization-crystallization method using L-3-amino-epsilon-caprolactam. The alkyl compounds (2) and the optical active compounds ((+)-2i, (-)-2i) were evaluated for aldose reductase inhibitory potency.
Ohishi
Y
Y
Central Research Institute, Kaken Pharmaceutical Co., Ltd., Kyoto, Japan.
Mukai
T
T
Nagahara
M
M
Yajima
M
M
Kajikawa
N
N
D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors*; D000818:Animals; D051381:Rats; D012236:Rhodanine / Q000031:analogs & derivatives*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D013844:Thiazoles; D012236:Rhodanine; D000449:Aldehyde Reductase