3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone as a potent and orally active cyclooxygenase-2 selective inhibitor: synthesis and biological evaluation.

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Khanapure SP, Augustyniak ME, Earl RA, Garvey DS, Letts LG, Martino AM, Murty MG, Schwalb DJ, Shumway MJ, Trocha AM, Young DV, Zemtseva IS, Janero DR

3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)(2-pyridyl) phenyl ketone as a potent and orally active cyclooxygenase-2 selective inhibitor: synthesis and biological evaluation.

J Med Chem. 2005 Jun 2;48(11):3930-4.

PubMed ID

15916445 [ View in PubMed

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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.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Celecoxib	Prostaglandin G/H synthase 2	IC 50 (nM)	1200	N/A	N/A	Details
Etoricoxib	Prostaglandin G/H synthase 2	IC 50 (nM)	2000	N/A	N/A	Details
Rofecoxib	Prostaglandin G/H synthase 2	IC 50 (nM)	500	N/A	N/A	Details