Synthesis of prostanoids with bicyclo[2.2.1]heptane, bicyclo[3.1.1]heptane, and bicyclo[2.2.2]octane ring systems. Activities of 15-hydroxy epimers on human platelets.
A number of prostanoids with bicyclo[2.2.1]heptane, bicyclo[3.1.1]heptane, and bicyclo[2.2.2]octane ring systems have been prepared by routes which allow the introduction of the omega chain after the alpha chain. The introduction of a 16-p-halophenoxy substituent confers platelet aggregation activity on both 15 alpha- and 15 beta-hydroxy epimers. In the case of the pinane thromboxane ring system, the natural omega-chain compound is an inhibitor of aggregation, whereas the 16-p-fluorophenoxy analogue is a potent aggregation agent.
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D006801:Humans; D066298:In Vitro Techniques; D010974:Platelet Aggregation / Q000187:drug effects*; D011465:Prostaglandins, Synthetic / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D011465:Prostaglandins, Synthetic