O2-Acetoxymethyl-protected diazeniumdiolate-based NSAIDs (NONO-NSAIDs): Synthesis, nitric oxide release, and biological evaluation studies

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 14, 2007, Pages 4767-4774

  Velázquez, Carlos A ^a   Praveen Rao, P N ^b   Citro, Michael L ^c   Keefer, Larry K ^a   Knaus, Edward E ^b  

^a NATIONAL CANCER INSTITUTE   (United States)

^b UNIVERSITY OF ALBERTA   (Canada)

^c SAIC FREDERICK INC   (United States)

Author keywords

Anti inflammatories; Cyclooxygenase inhibition; Diazeniumdiolates; Nitric oxide donors; Non ulcerogenic NSAIDs

Indexed keywords

2 O ACETOXYMETHYL 1 [N [2 (ACETYLSALICYLOYLOXY)ETHYL] N METHYLAMINO]DIAZEN 1 IUM 1,2 DIOLATE; 2 O ACETOXYMETHYL 1 [N [2 [2 [1 (4 CHLOROBENZOYL) 5 METHOXY 2 METHYL 1H INDOL 3 YL]ACETOXY]ETHYL] N METHYLAMINO]DIAZEN 1 IUM 1,2 DIOLATE; 2 O ACETOXYMETHYL 1 [N [2 [2 [4 (ISOBUTYL)PHENYL]PROPANOYLOXY]ETHYL] N METHYLAMINO]DIAZEN 1 IUM 1,2 DIOLATE; ACETYLSALICYLIC ACID; CARRAGEENAN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; ESTERASE; IBUPROFEN; INDOMETACIN; LIVER ENZYME; NITRIC OXIDE; NONSTEROID ANTIINFLAMMATORY AGENT; UNCLASSIFIED DRUG; ANTIINFLAMMATORY AGENT; OLEIC ACID; OXYGEN; PROSTAGLANDIN SYNTHASE INHIBITOR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; CARDIOVASCULAR DISEASE; CHEMOPROPHYLAXIS; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME MECHANISM; ESTERIFICATION; GASTROINTESTINAL TOXICITY; HEART INFARCTION; IC 50; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PAW EDEMA; RAT; STOMACH ULCER; STROKE; SWINE; THROMBOGENESIS; ULCEROGENESIS; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ENZYME ACTIVATION; METABOLISM; METHYLATION; PATHOLOGY; SHEEP; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

RATTUS; SUS;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; ENZYME ACTIVATION; METHYLATION; MOLECULAR STRUCTURE; NITRIC OXIDE; OLEIC ACID; OXYGEN; RATS; SHEEP; STOMACH ULCER; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34249687023     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.05.009     Document Type: Article

References (38)

1. Singh G., and Triadafilopoulos G. J. Rheumatol. Suppl. 56 (1999) 18
2. Go M.F. Gastrointest. Endosc. Clin. N. Am. 16 (2006) 83
3. Naesdal J., and Brown K. Drug Saf. 29 (2006) 119
4. Cryer B. Am. J. Gastroenterol. 100 (2005) 1694
5. Lazzaroni M., and Bianchi P.G. Aliment. Pharmacol. Ther. 20 (2004) 48
6. James M.W., and Hawkey C.J. Br. J. Clin. Pharmacol. 56 (2003) 146
7. Schneider V., Levesque L.E., Zhang B., Hutchinson T., and Brophy J.M. Am. J. Epidemiol. 164 (2006) 881
8. Mounier G., Guy C., Berthoux F., Beyens M.N., Ratrema M., and Ollagnier M. Therapie 61 (2006) 255
9. Zadrazil J. Vnitr. Lek. 52 (2006) 686
10. Adebayo D., and Bjarnason I. Postgrad. Med. J. 82 (2006) 186
11. Fiorucci S., and Antonelli E. Inflamm. Allergy Drug Targets 5 (2006) 121
12. Sanmuganathan P.S., Ghahramani P., Jackson P.R., Wallis E.J., and Ramsay L.E. Heart 85 (2001) 265
13. Collaborative overview of randomised trials of antiplatelet therapy-I: prevention of death, myocardial infarction, and stroke by prolonged antiplatelet therapy in various categories of patients. Antiplatelet Trialists' Collaboration. BMJ 1994, 308, 81.
14. Arber N., and Levin B. Curr. Top. Med. Chem. 5 (2005) 517
15. Dogne J.M., Supuran C.T., and Pratico D. J. Med. Chem. 48 (2005) 2251
16. Scheen A.J. Rev. Med. Liege 59 (2004) 565
17. Chiroli V., Benedini F., Ongini E., and Del S.P. Eur. J. Med. Chem. 38 (2003) 441
18. Nitronaproxen: AZD 3582, HCT 3012, Naproxen Nitroxybutylester, NO-Naproxen. Drugs R.D. 2006, 7, 262.
19. Holm L., Phillipson M., and Perry M.A. Am. J. Physiol. Gastrointest. Liver Physiol. 283 (2002) G1090
20. Wallace J.L., Muscara M.N., De Nucci G., Zamuner S., Cirino G., Del Soldato P., and Ongini E. J. Pharmacol. Exp. Ther. 309 (2004) 626
21. Wallace J.L., Reuter B., Cicala C., McKnight W., Grisham M., and Cirino G. Eur. J. Pharmacol. 257 (1994) 249
22. Rigas B., and Kashfi K. Trends Mol. Med. 10 (2004) 324
23. Wallace J.L., McKnight W., Reuter B., Cicala C., Grisham M., and Cirino G. Gastroenterology 106 (1994) A208
24. Wallace J.L., Reuter B.K., and Cirino G. J. Gastroenterol. Hepatol. 9 (1994) S40
25. Csont T., and Ferdinandy P. Pharmacol. Ther. 105 (2005) 57
26. Hu, R.; Siu, C.W.; Lau, E.-O.; Wang, W.Q.; Lau, C.-P.; Tse, H.-F. Int. J. Cardiol. 2007, doi :10.1016/j.ijcard.2006.10.011.
27. Fung H.L., and Bauer J.A. Cardiovasc. Drugs Ther. 8 (1994) 489
28. Keefer L.K. Annu. Rev. Pharmacol. Toxicol. 43 (2003) 585
29. Velazquez C., Praveen Rao P.N., and Knaus E.E. J. Med. Chem. 48 (2005) 4061
30. Velazquez C., and Knaus E.E. Bioorg. Med. Chem. 12 (2004) 3831
31. 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
32. Perini R., Fiorucci S., and Wallace J.L. Can. J. Gastroenterol. 18 (2004) 229
33. Bastaki S.M., and Wallace J.L. Can. J. Gastroenterol. 13 (1999) 123
34. Wallace J.L. Scand J. Gastroenterol. Suppl. 192 (1992) 3
35. Keefer L.K., Nims R.W., Davies K.M., and Wink D.A. Methods Enzymol. 268 (1996) 281
36. Winter C.A., Risley E.A., and Nuss G.W. Proc. Soc. Exp. Biol. Med. 111 (1962) 544
37. Cocco M.T., Congiu C., Onnis V., Morelli M., Felipo V., and Cauli O. Bioorg. Med. Chem. 12 (2004) 4169 and references cited therein
38. Uddin M.J., Rao P.N., and Knaus E.E. Bioorg. Med. Chem. 12 (2004) 5929