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.
Copyright © 2011 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Cell Line, Tumor
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Cyclooxygenase 2 Inhibitors / chemical synthesis*
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Cyclooxygenase 2 Inhibitors / pharmacology*
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Dinoprostone / antagonists & inhibitors*
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Female
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Humans
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Inflammatory Breast Neoplasms / drug therapy*
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Pyrroles / chemical synthesis*
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Pyrroles / pharmacology*
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Sulfonamides / chemical synthesis*
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Sulfonamides / pharmacology*
Substances
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Cyclooxygenase 2 Inhibitors
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Pyrroles
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Sulfonamides
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apricoxib
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Dinoprostone