Efficient synthesis of apricoxib, CS-706, a selective cyclooxygenase-2 inhibitor, and evaluation of inhibition of prostaglandin E2 production in inflammatory breast …

…, AL Bagsby, FM Robertson, JS McMurray

Index: Mandal, Pijus K.; Freiter, Eric M.; Bagsby, Allison L.; Robertson, Fredika M.; McMurray, John S. Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 20 p. 6071 - 6073

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Citation Number: 6

Abstract

An efficient synthesis of apricoxib (CS-706), a selective cyclooxygenase inhibitor, was developed using copper catalyzed homoallylic ketone formation from methyl 4- ethoxybenzoate followed by ozonolysis to an aldehyde, and condensation with sulfanilamide. This method provided multi-gram access of aprocoxib in good yield. Apricoxib exhibited potency equal to celecoxib at inhibition of prostaglandin E2 synthesis in two ...