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Four stereoisomers of 7-oxabicyclo[2.2.1]heptane derivatives with the benzenesulfonylamino group, 11, 14, 23 and 33, were synthesized and their sodium salts were examined in vitro for inhibitory activity against aggregation of rabbit platelet-rich plasma and of rat washed platelets. The trans-isomer 23 exhibited high potency but showed a partial agonistic effect. Compound 11 did not show a partial agonistic effect, though it was a less active inhibitor. The following trans compounds were synthesized and their IC50 values were measured: homologated trans-isomers with one methylene chain (47 and 53), an olefin derivative (58), and optically active derivatives [-)-11 and (+)-23).

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Thromboxane A2 receptor antagonists. I. Synthesis and pharmacological activity of 7-oxabicyclo-(2.2.1)heptane derivatives with the benzenesulfonylamino group.