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Design, synthesis, and biological evaluation of ketoprofen analogs as potent cyclooxygenase-2 inhibitors. 2010

Afshin Zarghi, and Razieh Ghodsi
Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran. azarghi@yahoo.com

A new series of ketoprofen analogs were synthesized to evaluate their biological activities as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 inhibition studies showed that all compounds were potent and selective inhibitors of the COX-2 isozyme with IC(50) values in the highly potent 0.057-0.085 microM range, and COX-2 selectivity indexes in the 115 to >1298.7 range. Compounds possessing azido pharmacophore group (8a and 8b) exhibited highly COX-2 inhibitory selectivity and potency even more than reference drug celecoxib. Molecular modeling studies indicated that the azido substituent can be inserted deeply into the secondary pocket of COX-2 active site for interactions with Arg(513).

UI MeSH Term Description Entries
D007660 Ketoprofen An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis. Benzoylhydratropic Acid,19,583 RP,2-(3-Benzoylphenyl)propionic Acid,Alrheumat,Alrheumum,Orudis,Profenid,RP-19583,RP 19583,RP, 19,583,RP19583
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D012756 Sheep Any of the ruminant mammals with curved horns in the genus Ovis, family Bovidae. They possess lachrymal grooves and interdigital glands, which are absent in GOATS. Ovis,Sheep, Dall,Dall Sheep,Ovis dalli
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D051379 Mice The common name for the genus Mus. Mice, House,Mus,Mus musculus,Mice, Laboratory,Mouse,Mouse, House,Mouse, Laboratory,Mouse, Swiss,Mus domesticus,Mus musculus domesticus,Swiss Mice,House Mice,House Mouse,Laboratory Mice,Laboratory Mouse,Mice, Swiss,Swiss Mouse,domesticus, Mus musculus
D051545 Cyclooxygenase 1 A constitutively-expressed subtype of prostaglandin-endoperoxide synthase. It plays an important role in many cellular processes. Prostaglandin H Synthase-1,COX-1 Prostaglandin Synthase,Cyclo-Oxygenase I,Cyclooxygenase-1,COX 1 Prostaglandin Synthase,Cyclo Oxygenase I,Prostaglandin H Synthase 1,Prostaglandin Synthase, COX-1,Synthase, COX-1 Prostaglandin
D051546 Cyclooxygenase 2 An inducibly-expressed subtype of prostaglandin-endoperoxide synthase. It plays an important role in many cellular processes and INFLAMMATION. It is the target of COX2 INHIBITORS. COX-2 Prostaglandin Synthase,Cyclo-Oxygenase II,Cyclooxygenase-2,PGHS-2,PTGS2,Prostaglandin H Synthase-2,COX 2 Prostaglandin Synthase,Cyclo Oxygenase II,Prostaglandin H Synthase 2,Prostaglandin Synthase, COX-2,Synthase, COX-2 Prostaglandin
D052246 Cyclooxygenase 2 Inhibitors A subclass of cyclooxygenase inhibitors with specificity for CYCLOOXYGENASE-2. COX-2 Inhibitor,COX2 Inhibitor,Coxib,Cyclooxygenase 2 Inhibitor,Cyclooxygenase-2 Inhibitor,COX-2 Inhibitors,COX2 Inhibitors,Coxibs,Cyclooxygenase-2 Inhibitors,2 Inhibitor, Cyclooxygenase,COX 2 Inhibitor,COX 2 Inhibitors,Inhibitor, COX-2,Inhibitor, COX2,Inhibitor, Cyclooxygenase 2,Inhibitor, Cyclooxygenase-2,Inhibitors, COX-2,Inhibitors, COX2,Inhibitors, Cyclooxygenase 2,Inhibitors, Cyclooxygenase-2

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