Synthesis and biological evaluation of 9,11-azo-13-oxa-15-hydroxyprostanoic acid, a potent inhibitor of platelet aggregation.
The synthesis of a prostaglandin endoperoxide analogue, 9,11-azo-13-oxa-15-hydroxyprostanoic acid (AOHP), is described. AOHP was found to block effectively both the thromboxane synthetase and the PGH2/TxA2 receptors in human platelets. It inhibits the platelet aggregation induced by arachidonic acid, 9.11-methanoepoxy-PGH2, PGH2, and TxA2 but does not affect the ADP-induced aggregation in aspirinated platelet-rich plasma. Some of the intermediates for the synthesis of AOHP also are effective in inhibiting platelet aggregation.
D001095:Arachidonic Acids / Q000037:antagonists & inhibitors / Q000097:blood; D001391:Azo Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D001792:Blood Platelets / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D006860:Hydrogen Bonding; D066298:In Vitro Techniques; D010974:Platelet Aggregation / Q000187:drug effects*; D011450:Prostaglandin Endoperoxides, Synthetic / Q000138:chemical synthesis* / Q000494:pharmacology; D011463:Prostaglandins H / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship; D013928:Thromboxane A2 / Q000037:antagonists & inhibitors
C022281:9,11-azo-13-oxa-15-hydroxyprostanoic acid; D001095:Arachidonic Acids; D001391:Azo Compounds; D011450:Prostaglandin Endoperoxides, Synthetic; D011463:Prostaglandins H; D013928:Thromboxane A2