Synthesis and biological evaluation of 9,11-azo-13-oxa-15-hydroxyprostanoic acid, a potent inhibitor of platelet aggregation

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Abstract
The synthesis of a prostaglandin endoperoxide analog, 9,11-azo-13-oxa-15-hydroxyprostanoic acid (AOHP), for possible use as an antithrombotic agent is described. AOHP effectively blocked both the thromboxane synthetase and the PG[prostaglandin]H2/Tx[thromboxane]A2 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.