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4,5‐Diaryloxazole inhibitors of cyclooxygenase‐2 (COX‐2)
Author(s) -
Talley John J.,
Bertenshaw Stephen R.,
Brown David L.,
Carter Jeffery S.,
Graneto Mathew J.,
Koboldt Carol M.,
Masferrer Jaime L.,
Norman Bryan H.,
Rogier D. Joseph,
Zweifel Ben S.,
Seibert Karen
Publication year - 1999
Publication title -
medicinal research reviews
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.868
H-Index - 130
eISSN - 1098-1128
pISSN - 0198-6325
DOI - 10.1002/(sici)1098-1128(199905)19:3<199::aid-med1>3.0.co;2-7
Subject(s) - cyclooxygenase , in vivo , chemistry , in vitro , pharmacology , stereochemistry , enzyme , enzyme inhibitor , selectivity , biochemistry , medicine , biology , catalysis , microbiology and biotechnology
A series of methysulfonyl or sulfonamido substituted 4,5‐diaryloxazole were prepared and evaluated for their ability to inhibit the inducible form of cyclooxygenase (COX‐2) in vitro and in vivo. Several unique substitution patterns were identified that led to potent and selective inhibitors of COX‐2. In general, 2‐trifluoromethly‐4,5‐diaryloxazoles substituted with a methylsulfonyl or sulfonamido group were particularly potent inhibitors. One of the more potent compounds with a selectivity for COX‐2 of about 800 fold was 4b (SC‐299). SC‐299, a highly fluorescent molecule, may be useful for spectroscopic studies on preferential inhibitor binding to COX‐2. © 1999 John Wiley & Sons, Inc. Med Res Rev, 19, No. 3, 199–208, 1999.