Synthesis and Pharmacological Evaluation of 5,6-exo-Epoxy-7-oxabicycloheptane Derivatives

Article abstract of DOI:10.1021/jm00400a007

<1α,2β,(5Z),3β(1E,5S),4α,5α,6α>-7-<5,6-Epoxy-3-(3-cyclohexyl-3-hydroxy-3-methyl-1-propenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (31) and <1α,2β(5Z),3β(1E,3S),4α,5α,6α>-7-<5,6-epoxy-3-<3-hydroxy-5-(p-hydroxyphenyl)-1-pentanyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (37) were found to be selective TxA₂ antagonists at the platelet and pulmonary thromboxane receptors.An efficient stereospecific synthesis of these compounds and a series of structural analogues is described.Compounds 31 and 37 both inhibited the bronchoconstriction induced by arachidonic acid in the anesthetized guinea pig.