Celecoxib analogs possessing a N-(4-nitrooxybutyl)piperidin-4-yl or N-(4-nitrooxybutyl)-1,2,3,6-tetrahydropyridin-4-yl nitric oxide donor moiety: Synthesis, biological evaluation and nitric oxide release studies

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 4, 2010, Pages 1324-1329

  Chowdhury, Morshed A ^a   Abdellatif, Khaled R A ^a   Dong, Ying ^a   Yu, Gang ^a   Huang, Zhangjian ^a   Rahman, Moshfiqur ^a   Das, Dipankar ^a   Velázquez, Carlos A ^a   Suresh, Mavanur R ^a   Knaus, Edward E ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

1,2,3,6 Tetrahydropyridine; Anti inflammatory activity; Cyclooxygenase 1 and cyclooxygenase 2 inhibition; Nitrate prodrugs; Piperidine

Indexed keywords

1 (4 AMINOSULFONYLPHENYL) 5 [1 (4 NITROOXYBUTYL) 1,2,3,6 TETRAHYDROPYRIDIN 4 YL] 3 TRIFLUOROMETHYL 1H PYRAZOLE; 1 (4 AMINOSULFONYLPHENYL) 5 [1 (4 NITROOXYBUTYL)PIPERIDIN 4 YL] 3 TRIFLUOROMETHYL 1H PYRAZOLE; 1 (4 METHANESULFONYLPHENYL) 5 [1 (4 NITROOXYBUTYL) 1,2,3,6 TETRAHYDROPYRIDIN 4 YL] 3 TRIFLUOROMETHYL 1H PYRAZOLE; 1 (4 METHANESULFONYLPHENYL) 5 [1 (4 NITROOXYBUTYL)PIPERIDIN 4 YL] 3 TRIFLUOROMETHYL 1H PYRAZOLE; ACETYLSALICYLIC ACID; CELECOXIB; CELECOXIB DERIVATIVE; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYSTEINE; IBUPROFEN; NITRATE; NITRIC OXIDE DONOR; PHOSPHATE BUFFERED SALINE; PIPERIDINE DERIVATIVE; PRODRUG; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; PH; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ASPIRIN; CRYSTALLOGRAPHY, X-RAY; CYCLOOXYGENASE 2 INHIBITORS; HUMANS; HYDROGEN-ION CONCENTRATION; IBUPROFEN; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NITRIC OXIDE; NITRIC OXIDE DONORS; PIPERIDINES; PRODRUGS; PYRAZOLES; RATS; SHEEP; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 75749092949     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.01.014     Document Type: Article

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29. 2 gas to remove any air or argon from the hydrogenation flask.
30. 50 value, μM) was determined using an enzyme immuno assay (EIA) kit (Catalog No. 560131, Cayman Chemical, Ann Arbor, MI, USA) according to our previously reported method (Rao, P. N. P.; Amini, M.; Li, H.; Habeeb, A.; Knaus, E. E. J. Med. Chem. 2003, 46, 4872).
31. -2 mM solution in phosphate buffer at pH 7.4 was determined by quantification of nitrite produced by the reaction of nitric oxide with oxygen and water using the Griess reaction. Nitric oxide release data were acquired for test compounds (15a-b, 17a-b) using the reported procedures (Velázquez, C.; Vo, D.; Knaus, E. E. Drug Dev. Res. 2003, 60, 204).
32. In vivo anti-inflammatory assay: The test compounds 15a-b, 17a-b, and the reference drugs celecoxib, aspirin, and ibuprofen were evaluated using the in vivo carrageenan-induced rat foot paw edema model reported previously (Winter, C. A.; Risley, E. A.; Nuss, G. W. Proc. Soc. Exp. Biol. Med. 1962, 111, 544).