Diazen-1-ium-1,2-diolated nitric oxide donor ester prodrugs of 5-(4-carboxymethylphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-pyrazole and its aminosulfonyl analog: Synthesis, biological evaluation and nitric oxide release studies

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 14, 2009, Pages 5182-5188

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

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Anti inflammatory activity; Cyclooxygenase inhibition; Diazen 1 ium 1,2 diolate nitric oxide donor; NONO coxib ester prodrugs

Indexed keywords

5 (4 CARBOXYMETHYLPHENYL) 1 (4 AMINOSULFONYLPHENYL) 3 TRIFLUOROMETHYL 1H PYRAZOLE; 5 (4 CARBOXYMETHYLPHENYL) 1 (4 METHANESULFONYLPHENYL) 3 TRIFLUOROMETHYL 1H PYRAZOLE; ACETYLSALICYLIC ACID; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; ETORICOXIB; IBUPROFEN; LUMIRACOXIB; NITRIC OXIDE; NITRIC OXIDE DONOR ESTER PRODRUG DIAZEN 1 IUM 1,2 DIOLATE; NITROOXYETHYL ESTER PRODRUG; NONSTEROID ANTIINFLAMMATORY AGENT; O 2 ACETOXYMETHYL 1 [2 [2 [4 [1 (4 AMINOSULFONYLPHENYL) 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL]PHENYL]ACETOXYMETHYL]PYRROLIDIN 1 YL]DIAZEN 1 IUM 1,2 DIOLATE; O 2 ACETOXYMETHYL 1 [N [2 [2 [4 [1 (4 AMINOSULFONYLPHENYL) 3 TRIFLUOROMETHYL 1H PYRAZOL 5 YL]PHENYL]ACETOXY]ETHYL] N METHYLAMINO]DIAZEN 1 IUM 1,2 DIOLATE; PRODRUG; PROSTAGLANDIN SYNTHASE INHIBITOR; PYRAZOLE DERIVATIVE; ROFECOXIB; UNCLASSIFIED DRUG; VALDECOXIB;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARDIOVASCULAR DISEASE; CHRONIC PAIN; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; NONHUMAN; PROSTAGLANDIN SYNTHESIS INHIBITION; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; ANTI-INFLAMMATORY AGENTS; AZO COMPOUNDS; CYCLOOXYGENASE INHIBITORS; EDEMA; FOOT; HUMANS; NITRIC OXIDE; NITRIC OXIDE DONORS; PRODRUGS; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; RATS; SHEEP;

RATTUS;

EID: 67650097233     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.05.046     Document Type: Article

References (27)

1. Harris C.R., and Breyer D.M. Clin. J. Am. Soc. Nephrol. 1 (2006) 236
2. Neiderberger E., Manderscheid C., and Geisslinger G. Biochem. Biophy. Res. Commun. 342 (2006) 940
3. Hinz B., and Brune K. J. Pharmacol. Exp. Ther. 300 (2002) 367
4. Patel H.H., and Gross G.J. J. Mol. Cell Cardiol. 34 (2002) 1
5. Mukherjee D. Biochem. Pharmacol. 63 (2002) 817
6. Scheen A.J. Rev. Med. Liege 59 (2004) 565
7. Dogné J.-M., Supuran C.T., and Pratico D. J. Med. Chem. 48 (2005) 2251
8. Butler A.R., and Williams D.L.H. Chem. Soc. Rev. 22 (1993) 233
9. Anning B.P., Coles B., Morton J., Wang H., Uddin J., Morrow D.J., Dey K.S., Marnett J.L., and O'Donell B.V. Blood 108 (2006) 4059
10. Abdellatif K.R.A., Chowdhury M.A., Dong Y., Chen Q.-H., and Knaus E.E. Bioorg. Med. Chem. 16 (2008) 3302
11. Abdellatif K.R.A., Chowdhury M.A., Dong Y., Velázquez C.A., Das D., Suresh M.R., and Knaus E.E. Bioorg. Med. Chem. 16 (2008) 9694
12. Abdellatif K.R.A., Dong Y., Chen Q.-H., Chowdhury M.A., and Knaus E.E. Bioorg. Med. Chem. 15 (2007) 6796
13. Csont T., and Ferdinandy P. Pharmacol. Ther. 105 (2005) 57
14. Fung H.L., and Bauer J.A. Cardiovasc. Drugs Ther. 8 (1994) 489
15. Hu R., Siu C.W., Lau E.O., Wang W.Q., Lau C.-P., and Tse H.-F. Int. J. Cardiol. 120 (2007) 351
16. Penning T.D., Tally J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Doctor S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., and Isakson P.C. J. Med. Chem. 40 (1997) 1347
17. Ahlström M.M., Ridderström M., Zamora I., and Luthman K. J. Med. Chem. 50 (2007) 4444
18. Borne R., Levi M., and Wilson N. In: Lemke T.L., Williams D.A., Roche V.F., and Zito S.W. (Eds). Foye's Principles of Medicinal Chemistry. 6th ed. (2008), Lippincott Williams and Wilkins, Philadelphia 987 Chapter 36
19. Saavedra J.E., Dunams T.M., Flippen-Anderson J.L., and Keefer L.K. J. Org. Chem. 57 (1992) 6134
20. Hrabie J.A., Klose J.R., Wink D.A., and Keefer L.K. J. Org. Chem. 58 (1993) 1472
21. Saavedra J.E., Shami P.J., Wang L.Y., Davies K.M., Booth M.N., Citro M.L., and Keefer L.K. J. Med. Chem. 43 (2000) 261
22. Velázquez C.A., Praveen Rao P.N., Citro M.L., Keefer L.K., and Knaus E.E. Bioorg. Med. Chem. 15 (2007) 4767
23. Velazquez C., and Knaus E.E. Bioorg. Med. Chem. 12 (2004) 3831
24. Velázquez C., Chen Q.-H., Citro M.L., Keefer L.K., and Knaus E.E. J. Med. Chem. 51 (2008) 1954
25. Rao P.N.P., Amini M., Li H., Habeeb A., and Knaus E.E. J. Med. Chem. 46 (2003) 4872
26. Velázquez C., Vo D., and Knaus E.E. Drug Dev. Res. 60 (2003) 204
27. Winter C.A., Risley E.A., and Nuss G.W. Proc. Soc. Exp. Biol. Med. 111 (1962) 544