3-Phenyl-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]indole-2-carbonitrile, a potent inhibitor of prostaglandin synthetase and of platelet aggregation

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Abstract
A number of indoles containing the 2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl side chain were prepared by standard methods. Alternate, novel synthesis of indole-2-carboxamides and indole-2-carbonitriles were developed. The title compound, 7e [indole-2-carbonitrile], was a potent inhibitor of bovine prostaglandin synthetase in vitro and lowered serum prostaglandin levels after oral or i.p. administration to rats. Consistent with prostaglandin synthetase inhibition, 7e prevented arachidonic acid induced diarrhea in mice and also collagen, ADP or epinephrine induced platelet aggregation in human platelet-rich plasma. In contrast to many prostaglandin synthetase and platelet-aggregation inhibitors, 7e had neither ulcerogenicity nor systemic antiinflammatory activity in rats.

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