Synthesis and aldose reductase inhibitory activities of benzyl 2-oxazolecarbamate analogues.
Various analogues of benzyl 5-phenyl-2-oxazolecarbamate (1a) were synthesized, and the structure-activity relationship of these analogues as aldose reductase inhibitor was studied. The carbamate group was necessary for the inhibitory activity. The introduction of an alkyl group at the C-4 position of 1a enhanced the inhibitory activity, however, the N-carboxymethyl group on the carbamate moiety counteracted to a hydrophobic interaction between the alkyl group at the C-4 position and the enzyme molecule.
Miyahara
N
N
Osaka University of Pharmaceutical Sciences, Japan.
Kasugai
Y
Y
Ohmomo
Y
Y
Tanaka
C
C
Tanimoto
T
T
D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors*; D000818:Animals; D002219:Carbamates / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D007908:Lens, Crystalline / Q000201:enzymology; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D011817:Rabbits
D002219:Carbamates; D010080:Oxazoles; C074372:benzyl 5-phenyl-2-oxazolecarbamate; D000449:Aldehyde Reductase