Synthesis and Prostaglandin-like Activity of 2-(trans-3-Hydroxy-1-octenyl)-3-indolheptanoic Acid

The synthesis of 2-(trcms-3-hydroxy-l-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 103- and 102-fold higher, respectively, than PGE1 Moreover, it stimulated adenylate cyclase from rat liver plasma membrane, but the relative potency was 4-5 x 102-fold lower than the natural compound. The title compound showed also a certain degree of PGE1 antagonism. © 1978, American Chemical Society. All rights reserved.

The synthesis of 2-(trans-3-hydroxy-l-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 lo3- and 102-fold higher, respectively, than PGE]. Moreover, it stimulated adenylate cyclase from rat liver plasma membrane, but the relative potency was 4-5 X 102-fold lower than the natural compound. The title compound showed also a certain degree of PGE, antagonism.