Studies on Hypolipidemic Agents. IV. Syntheses and Biological Activities of trans-and cis-2- (4-Alkylcyclohexyl) -2-oxoethyl Arenesulfonates

KAZUO OGAWA; TADAFUMI TERADA; YOSHIYUKI MURANAKA; TOSHIHIRO HAMAKAWA; SHUNSAKU OHTA; MASAO OKAMOTO; SETSURO FUJII

doi:10.1248/cpb.35.3276

Studies on Hypolipidemic Agents. IV. Syntheses and Biological Activities of trans-and cis-2- (4-Alkylcyclohexyl) -2-oxoethyl Arenesulfonates

KAZUO OGAWA, TADAFUMI TERADA, YOSHIYUKI MURANAKA, TOSHIHIRO HAMAKAWA, SHUNSAKU OHTA, MASAO OKAMOTO, SETSURO FUJII

Author information

Keywords: diazoketone, trans-arenesulfonate, cis-arenesulfonate, 4-alkylcyclohexyl methylketone, α-bromoketone, α-hydroxyketone, esterase-inhibitory activity, chymotrypsin-inhibitory activity, hypolipidemic activity, structure-activity relationship

JOURNAL FREE ACCESS

1987 Volume 35 Issue 8 Pages 3276-3283

DOI https://doi.org/10.1248/cpb.35.3276

Details

Abstract

trans-and cis-2-Diazo-1- (4-alkylcyclohexyl) -1-ethanones were reacted with arenesulfonic acids to afford the corresponding 2- (4-alkylcyclohexyl) -2-oxoethyl arenesulfonates. The esteraseinhibitory activity and hypolipidemic effect of the arenesulfonates were examined, and it was found that in most cases, the trans-isomers were more active than the corresponding cis-isomers.
Stereoselective syntheses of several biologically potent trans-isomers (trans-3) were also developed.

Corresponding author

Register with J-STAGE for free!