Synthesis and prostaglandin-like activity of 2-(trans-3-hydroxy-1-octenyl)-3-indoleheptanoic acid.
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.
D000818:Animals; D000242:Cyclic AMP / Q000378:metabolism; D006168:Guinea Pigs; D006538:Heptanoic Acids / Q000138:chemical synthesis / Q000494:pharmacology; D066298:In Vitro Techniques; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008099:Liver / Q000187:drug effects / Q000378:metabolism; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D011458:Prostaglandins E / Q000037:antagonists & inhibitors / Q000494:pharmacology; D011459:Prostaglandins E, Synthetic / Q000138:chemical synthesis*; D051381:Rats
D006538:Heptanoic Acids; D007211:Indoles; D011458:Prostaglandins E; D011459:Prostaglandins E, Synthetic; C018318:2-(trans-3-hydroxy-1-octenyl)-3-indoleheptanoic acid; D000242:Cyclic AMP