- 著者
- KAZUO OGAWA TADAFUMI TERADA YOSHIYUKI MURANAKA TOSHIHIRO HAMAKAWA SETSURO FUJII
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.35, no.10, pp.4130-4136, 1987-10-25 (Released:2009-10-19)
- 参考文献数
- 13
- 被引用文献数
- 3 4
2- (1, t- and c-4-Dialkylcyclohex-r-1-yl) -2-oxoethyl arenesulfonates, 2- (4, 4-dialkylcyclohex-1-yl) -2-oxoethyl arenesulfonates and related compounds were synthesized and evaluated for esteraseand chymotrypsin-inhibitory activities in vitro and for hypolipidemic effect in vivo. The transisomers of 2- (1, 4-dialkylcyclohex-1-yl) -2-oxoethyl arenesulfonates showed much more potent esterase-inhibitory action (about 13 to 6200 times) than the cis-isomers as well as more potent hypolipidemic action (about 1.5 to 10 times) but the chymotrypsin-inhibitory actions of the two isomers were similarly low. On the other hand, the 2-oxoethyl arenesulfonates having a 4, 4- disubstituted cyclohexane ring mostly exhibited potent esterase-inhibitory action (order of IC50; 10-8 to 10-9M) and marked hypolipidemic effect (78% to 95% reductions of plasma triglyceride).
- 著者
- KAZUO OGAWA TADAFUMI TERADA YOSHIYUKI MURANAKA TOSHIHIRO HAMAKAWA SHUNSAKU OHTA MASAO OKAMOTO SETSURO FUJII
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.35, no.8, pp.3276-3283, 1987-08-25 (Released:2009-10-19)
- 参考文献数
- 19
- 被引用文献数
- 5 8
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.
- 著者
- KAZUO OGAWA TADAFUMI TERADA YOSHIYUKI MURANAKA TOSHIHIRO HAMAKAWA SETSURO FUJII
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.35, no.6, pp.2426-2436, 1987-06-25 (Released:2009-10-19)
- 参考文献数
- 22
- 被引用文献数
- 2 4
Various ω-cycloalkyl-2-oxoalkyl arenesulfonates were synthesized and evaluated for esterase-and chymotrypsin-inhibitory activities and hypolipidemic activity. Among the tested compounds, 2-oxoalkyl arenesulfonates (4, 8 and 13) having a cyclohexyl substituent at the terminus of the alkyl chain exhibited considerable esterase-inhibitory activity, and several compounds among 4 and 8 also exhibited potent hypolipidemic action. The structure-activity relationships of these compounds are discussed.