11,12-Secoprostaglandins. 3. 8-Alkylthio(sulfinyl and sulfonyl)-12-hydroxyalkanoic acids and related compounds
- 1 April 1977
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 20 (4) , 540-547
- https://doi.org/10.1021/jm00214a016
Abstract
A series of 8-alkylthio(sulfinyl and sulfonyl)-12-hydroxyalkanoic acids which embody structural features of 11,12-secoprostaglandins was synthesized and evaluated for their ability to mimic the E series prostaglandins [PG] in stimulating c[cyclic]AMP formation in the mouse ovary and in binding to the rat lipocyte PG receptor. A key member of the series, 8-methylsulfonyl-12-hydroxyheptadecanoic acid, markedly stimulates cAMP formation at reasonable pharmacological concentrations, shows significant affinity for a PG receptor, and effectively inhibits antigen-induced lymphocyte transformation. This compound is not a substrate for 15-hydroxyprostaglandin dehydrogenase, the major PG-metabolizing enzyme.This publication has 3 references indexed in Scilit:
- 11,12-Secoprostaglandins. 2. N-Acyl-N-alkyl-7-aminoheptanoic acidsJournal of Medicinal Chemistry, 1977
- 11,12-Secoprostaglandins. 1. Acylhydroxyalkanoic acids and related compoundsJournal of Medicinal Chemistry, 1977
- Effects of Prostaglandins on Adenosine 3′,5′-Monophosphate Levels in Fat and Other TissuesJournal of Biological Chemistry, 1968