title: Efficient synthesis of apricoxib, CS-706, a selective cyclooxygenase-2 inhibitor, and evaluation of inhibition of prostaglandin E2 production in inflammatory breast cancer cells.
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 inflammatory breast cancer cell lines.
authors: Department of Experimental Therapeutics, M D Anderson Cancer Center, 1862 East Road, Houston, TX 77054-3005, USA.
authors: Pijus K
authors: PK
authors: Mandal
authors: Eric M
authors: EM
authors: Freiter
authors: Allison L
authors: AL
authors: Bagsby
authors: Fredika M
authors: FM
authors: Robertson
authors: John S
authors: JS
authors: McMurray
mesh_terms: D045744:Cell Line, Tumor; D052246:Cyclooxygenase 2 Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D015232:Dinoprostone / Q000037:antagonists & inhibitors*; D005260:Female; D006801:Humans; D058922:Inflammatory Breast Neoplasms / Q000188:drug therapy*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology*; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D052246:Cyclooxygenase 2 Inhibitors; D011758:Pyrroles; D013449:Sulfonamides; C514354:apricoxib; D015232:Dinoprostone