Article: 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone as a potent and orally active cyclooxygenase-2 selective inhibitor: synthesis and biological evaluation.
Journal of medicinal chemistry
2005 Volume 48, Issue 11, Page(s) 3930–3934
Abstract: Incorporation of a spacer group between the central scaffold and the aryl ring resulted in a new cyclooxygenase-2 (COX-2) selective inhibitor core structure, 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone (20), with COX-2 IC50 = ...
| Abstract | Incorporation of a spacer group between the central scaffold and the aryl ring resulted in a new cyclooxygenase-2 (COX-2) selective inhibitor core structure, 3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone (20), with COX-2 IC50 = 0.25 microM and COX-1 IC50 = 14 microM (human whole blood assay). Compound 20 was orally active in the rat air pouch model of inflammation, inhibiting white blood cell infiltration and COX-2-derived PG production. Our data support the identification of a novel COX-2 selective inhibitor core structure exemplified by 20. |
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| MeSH term(s) | Administration, Oral ; Animals ; Carrageenan ; Cyclooxygenase 2 ; Cyclooxygenase 2 Inhibitors ; Cyclooxygenase Inhibitors/chemical synthesis ; Cyclooxygenase Inhibitors/chemistry ; Cyclooxygenase Inhibitors/pharmacology ; Dinoprostone/antagonists & inhibitors ; Dinoprostone/biosynthesis ; Inflammation/chemically induced ; Inflammation/metabolism ; Male ; Prostaglandin-Endoperoxide Synthases/metabolism ; Pyridines/chemical synthesis ; Pyridines/chemistry ; Pyridines/pharmacology ; Rats ; Rats, Sprague-Dawley ; Sulfones/chemical synthesis ; Sulfones/chemistry ; Sulfones/pharmacology | ||||||||||
| Chemical Substances | 3-(4-(methylsulfonyl)phenyl)-5-(trifluoromethyl)(2-pyridyl) phenyl ketone ; Cyclooxygenase 2 Inhibitors ; Cyclooxygenase Inhibitors ; Pyridines ; Sulfones ; Carrageenan (9000-07-1) ; Cyclooxygenase 2 (EC 1.14.99.1) ; Prostaglandin-Endoperoxide Synthases (EC 1.14.99.1) ; Dinoprostone (K7Q1JQR04M) | ||||||||||
| Language | English | ||||||||||
| Publishing date | 2005-06-02 | ||||||||||
| Publishing country | United States | ||||||||||
| Document type | Journal Article | ||||||||||
| ZDB-ID | 218133-2 | ||||||||||
| ISSN | 1520-4804 ; 0022-2623 | ||||||||||
| ISSN (online) | 1520-4804 | ||||||||||
| ISSN | 0022-2623 | ||||||||||
| DOI | 10.1021/jm0582064 | ||||||||||
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| Database | MEDical Literature Analysis and Retrieval System OnLINE |
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