Synthesis and prostaglandin-like activity of 2-(trans-3-hydroxy-1-octenyl)-3-indoleheptanoic acid

• Published in: Journal of medicinal chemistry Vol. 21; no. 9; pp. 988 - 990
• Main Authors: Barco, A, Benetti, S, Pollini, G. P, Baraldi, P. G, Guarneri, M, Simoni, D, Vicentini, C. B, Borasio, P. G, Capuzzo, A
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 01.09.1978
• Subjects: Animals; Cyclic AMP - metabolism; Guinea Pigs; Heptanoic Acids - chemical synthesis; Heptanoic Acids - pharmacology; In Vitro Techniques; Indoles - chemical synthesis; Indoles - pharmacology; Liver - drug effects; Liver - metabolism; Muscle Contraction - drug effects; Muscle, Smooth - drug effects; Prostaglandins E - antagonists & inhibitors; Prostaglandins E - pharmacology; Prostaglandins E, Synthetic - chemical synthesis; Rats
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm00207a027

The synthesis of 2-(trans-3-hydroxy-1-octenyl)-3-indoleheptanoic acid (1) is described. The title compound appeared to show a weak prostaglandin-like activity in two different systems. It contracted rat stomach fundus strips and guinea-pig ileum preparations only at concentrations about 10(3)- and 10(2)-fold higher, respectively, than PGE1. Moreover, it stimulated adenylate cyclase from rat liver plasma membrane, but the relative potency was 4--5 X 10(2)-fold lower than the natural compound. The title compound showed also a certain degree of PGE1 antagonism.