Preparations of 5-alkylmethylidene-3-carboxymethylrhodanine derivatives and their aldose reductase inhibitory activity.
Reactions of 3-carboxymethylrhodanine (1) with aldehydes (2a-u) afforded stereoselectively the 5-mono-alkylmethylidene-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 alkylamino 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.
Ohishi
Y
Y
Central Research Institute, Kaken Pharmaceutical Co., Ltd., Kyoto, Japan.
Mukai
T
T
Nagahara
M
M
Yajima
M
M
Kajikawa
N
N
Miyahara
K
K
Takano
T
T
D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors*; D055598:Chemical Phenomena; D002621:Chemistry; D012235:Rhodamines / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014961:X-Ray Diffraction
D012235:Rhodamines; D000449:Aldehyde Reductase