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18-cycloalkyl analogues of enisoprost.

Abstract：

:By use of standard cuprate methodology, a series of 18-cycloalkyl analogues of enisoprost was prepared in an effort to impede omega chain metabolism and prolong duration of gastric antisecretory activity. An initial product of omega chain oxidation, the C-20 hydroxy analogue, was also synthesized for pharmacological comparison. The cyclopropyl, cyclobutyl, and cyclopentyl analogues were approximately one-fourth as potent as enisoprost in inhibiting gastric acid secretion, while the cyclohexyl and cycloheptyl analogues showed very weak activity, and the 20-hydroxy compound was inactive at a dose 100 times the ED50 of enisoprost. The cyclobutyl compound had a longer duration of antisecretory action than enisoprost and the other cycloalkyl analogues. The cycloalkyl analogues unexpectedly possessed low diarrheogenic activity in rats.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Collins PW,Gasiecki AF,Perkins WE,Gullikson GW,Jones PH,Bauer RF

doi

10.1021/jm00125a013

subject

Has Abstract

pub_date

1989-05-01 00:00:00

pages

1001-6

issue

5

eissn

0022-2623

issn

1520-4804

journal_volume

32

pub_type

杂志文章

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