Ethanesulfohydroxamic acid ester prodrugs of nonsteroidal anti-inflammatory drugs (NSAIDs): Synthesis, nitric oxide and nitroxyl release, cyclooxygenase inhibition, anti-inflammatory, and ulcerogenicity index studies

Journal of Medicinal Chemistry

Volumn 54, Issue 5, 2011, Pages 1356-1364

  Huang, Zhangjian ^a   Velázquez, Carlos A ^a   Abdellatif, Khaled R A ^a   Chowdhury, Morshed A ^a   Reisz, Julie A ^b   Dumond, Jenna F ^b   King, S Bruce ^b   Knaus, Edward E ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b WAKE FOREST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (PHENYLACETYLOXY)ETHANESULFONIC ACID SODIUM SALT; 2 (PHENYLACETYLOXY)ETHANESULFONYL CHLORIDE; 2 (PHENYLACETYLOXY)ETHANESULFONYLHYDROXAMIC ACID; 2 [2 (4 ISOBUTYLPHENYL)PROPIONOYLOXY]ETHANESULFONIC ACID SODIUM SALT; 2 [2 (4 ISOBUTYLPHENYL)PROPIONOYLOXY]ETHANESULFONYL CHLORIDE; 2 [2 (4 ISOBUTYLPHENYL)PROPIONOYLOXY]ETHANESULFONYLHYDROXAMIC ACID; 2 [2 (6 METHOXYNAPHTHYL 2 YL)PROPIONOYLOXY]ETHANESULFONIC ACID SODIUM SALT; 2 [2 (6 METHOXYNAPHTHYL 2 YL)PROPIONOYLOXY]ETHANESULFONYL CHLORIDE; 2 [2 (6 METHOXYNAPHTHYL 2 YL)PROPIONOYLOXY]ETHANESULFONYLHYDROXAMIC ACID; 2 [2 [1 (4 CHLOROBENZOYL) 2 METHYL 5 METHOXYL 1H INDOYL 3 YL]ACETOXY]ETHANESULFONIC ACID SODIUM SALT; 2 [2 [1 (4 CHLOROBENZOYL) 2 METHYL 5 METHOXYL 1H INDOYL 3 YL]ACETOXY]ETHANESULFONYL CHLORIDE; 2 [2 [1 (4 CHLOROBENZOYL) 2 METHYL 5 METHOXYL 1H INDOYL 3 YL]ACETOXY]ETHANESULFONYLHYDROXAMIC ACID; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; ETHANESULFOHYDROXAMIC ACID ESTER DERIVATIVE; IBUPROFEN; IBUPROFEN ACID CHLORIDE; INDOMETACIN; INDOMETACIN ACID CHLORIDE; N METHOXYL 2 [2 (4 ISOBUTYLPHENYL)PROPIONOYLOXY]ETHANESULFONYLAMIDE; NAPROXEN; NAPROXEN ACID CHLORIDE; NITRIC OXIDE; NONSTEROID ANTIINFLAMMATORY AGENT; PHENYLACETYL CHLORIDE; PROSTAGLANDIN SYNTHASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MALE; NONHUMAN; PAW EDEMA; RAT; STOMACH ULCER;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CARRAGEENAN; CYCLOOXYGENASE INHIBITORS; EDEMA; ESTERS; GASTRIC MUCOSA; HUMANS; HYDROXAMIC ACIDS; IBUPROFEN; INDOMETHACIN; MALE; NAPROXEN; NITRIC OXIDE DONORS; NITROGEN OXIDES; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM; STOMACH ULCER; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79952256512     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101403g     Document Type: Article

References (39)

1. Go, M. F. Drug injury in the upper gastrointestinal tract: nonsteroidal anti-inflammatory drugs Gastrointest. Endosc. Clin. N. Am. 2006, 16, 83-97
2. Naesdal, J.; Brown, K. NSAID-associated adverse effects and acid control aids to prevent them: a review of current treatment options Drug Saf. 2006, 29, 119-132 (Pubitemid 43213886)
3. Mounier, G.; Guy, C.; Berthoux, F.; Beyens, M. N.; Ratrema, M.; Ollagnier, M. Severe renal adverse events with arylcarboxylic nonsteroidal anti-inflammatory drugs: results of an eight-year French national survey Therapie 2006, 61, 255-266 (Pubitemid 350188090)
4. Zadrazil, J. Nonsteroidal antiinflammatory drugs and the kidney Vnitr. Lek. 2006, 52, 686-690 (Pubitemid 44276582)
5. Adebayo, D.; Bjarnason, I. Is non-steroidal anti-inflammaory drug (NSAID) enteropathy clinically more important than NSAID gastropathy Postgrad. Med. J. 2006, 82, 186-191
6. Mukherjee, D.; Nissen, S. E.; Topol, E. J. Risk of cardiovascular events associated with selective COX-2 inhibitors JAMA, J. Am. Med. Assoc. 2001, 286, 954-959 (Pubitemid 33010342)
7. Butler, A. R.; Williams, D. L. H. The physiological role of nitric oxide Chem. Soc. Rev. 1993, 22, 233-241
8. Anning, B. P.; Coles, B.; Morton, J.; Wang, H.; Uddin, J.; Morrow, D. J.; Dey, K. S.; Marnett, J. L.; O'Donell, B. V. Nitric oxide deficiency promotes vascular side effects of cyclooxygenase inhibitors Blood 2006, 108, 4059-4062 (Pubitemid 44913275)
9. 2-(acetoxymethyl)-1-(2-carboxypyrrolidin-1-yl)diazenium-1,2-diolate nitric oxide donor moiety: design, synthesis, biological evaluation, and nitric oxide release studies J. Med. Chem. 2008, 51, 1954-1961 (Pubitemid 351438876)
10. Hoffman, M. D.; Walsh, G. M.; Rogalski, J. C.; Kast, N. Identification of nitroxyl-induced modifications in human platelet proteins using a novel mass spectrometric detection method Mol. Cell. Proteomics 2009, 8, 887-903
11. Irvine, J. D.; Ritchie, D. H.; Favalora, J. L.; Andrews, K. L.; Widdip, R. E; Kemp-Harper, B. K. Nitroxyl (HNO): the cinderella of the nitric oxide story Trends Pharmacol. Sci. 2008, 29, 601-608
12. Paolocci, N.; Saavedra, W. F.; Miranda, K. M.; Martignani, C.; Isoda, T.; Hare, J. M.; Espey, M. G.; Fukuto, J. M.; Feelisch, M.; Wink, D. A.; Kass, D. A. Nitroxyl anion exerts redox-sensitive positive cardiac inotropy in vivo by calcitonin gene-related peptide signaling Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 10463-10468 (Pubitemid 32803042)
13. - in failing hearts: independence from β-adrenergic signaling Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5537-5542 (Pubitemid 36542740)
14. Pagliaro, P.; Mancardi, D.; Rastaldo, R.; Penna, C.; Gattullo, D.; Miranda, K. M.; Feelisch, M.; Wink, D. A.; Kass, D. A.; Paolocci, N. Nitroxyl affords thiol-sensitive myocardial protective effects akin to early preconditioning Free Radic. Biol. Med. 2003, 34, 33-43 (Pubitemid 36043884)
15. King, S. B.; Nagasawa, H. T. Chemical approaches toward generation of nitroxyl (HNO), in Methods in Enzymology; Packer, L., Ed.; Academic Press: New York, 1998; pp 211 - 220.
16. Huang, Z.; Velázquez, C. A.; Abdellatif, K.; Chowdhury, M.; Jain, S.; Reisz, J.; DuMond, J.; King, S. B.; Knaus, E. E. Acyclic triaryl olefins possessing a sulfohydroxamic acid pharmacophore: synthesis, nitric oxide/nitroxyl release, cyclooxygenase inhibition, and anti-inflammatory studies Org. Biomol. Chem. 2010, 8, 4124-4130
17. Shirota, F. N.; DeMaster, E. G.; Lee, M. J. C.; Nagasawa, H. T. Generation of nitric oxide and possibly nitroxyl by nitrosation of sulfohydroxamic acids and hydroxamic acids Nitric Oxide 1999, 3, 445-453 (Pubitemid 30070644)
18. Shoeman, D. W.; Nagasawa, H. T. The reaction of nitroxyl (HNO) with nitrosobenzene gives Cupferron (N -nitrosophenylhydroxylamine) Nitric Oxide 1998, 2, 66-72 (Pubitemid 28371232)
19. Abdellatif, K. R. A.; Chowdhury, M. A.; Dong, Y.; Das, D.; Yu, G.; Velázquez, C. A.; Suresh, M. R.; Knaus, E. E. Dinitroglyceryl and diazen-1-ium-1,2-diolated nitric oxide donor ester prodrugs of aspirin, indomethacin and ibuprofen: synthesis, biological evaluation and nitric oxide release studies Bioorg. Med. Chem. Lett. 2009, 19, 3014-3018
20. Meissner, D.; Schareina, T.; Grassert, I.; Oehme, G. Asymmetric hydrogenation of amino acid precursors promoted by a new type of cholesterol amphiphiles: investigation of aggregation behaviour and stereoselective effects J. Prakt. Chem. 1996, 338, 614-619
21. Goldberg, A. A. Isethionic Acid J. Chem. Soc. 1942, 716-718
22. Sha, X.; Isbell, T. S.; Patel, R. P.; Day, C. S.; King, S. B. Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO) J. Am. Chem. Soc. 2006, 128, 9687-9692 (Pubitemid 44147951)
23. Bonner, F. T.; Ko, Y. Kinetic, isotopic, and nitrogen-15 NMR study of N -hydroxybenzenesulfonamide decomposition: an nitrosyl hydride (HNO) source reaction Inorg. Chem. 1992, 31, 2514-2519
24. Donzelli, S.; Espey, M. G.; Thomas, D. D.; Mancardi, D.; Tocchetti, C. G.; Ridnour, L. A.; Paolocci, N.; King, S. B.; Miranda, K. M.; Lazzarino, G.; Fukuto, J. M.; Wink, D. A. Discriminating formation of HNO from other reactive nitrogen oxide species Free Radic. Biol. Med. 2006, 40, 1056-1066 (Pubitemid 43376015)
25. Luong, C.; Miller, A.; Barnett, J.; Chow, J.; Ramesha, C.; Browner, M. F. Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2 Nature Struct. Biol. 1996, 3, 927-933 (Pubitemid 26398325)
26. Jain, N. K.; Kulkarni, S. K.; Singh, A. Acute studies on safety index of nonsteroidal anti-inflammatory drugs in rats Inflammopharmacology 2001, 9, 229-240
27. Wallace, J. L.; Soldato, P. D. The therapeutic potential of NO-NSAIDs Fundam. Clin. Pharmacol. 2003, 17, 11-20 (Pubitemid 36241449)
28. Chiroli, V.; Benedini, F.; Ongini, E.; Del Soldato, P. Nitric oxide donating non-steroidal anti-inflammatory drugs: the case of nitro derivatives of aspirin Eur. J. Med. Chem. 2003, 38, 441-446 (Pubitemid 36577196)
29. Wallace, J. L.; Muscará, M. N.; De Nucci, G.; Zamuner, S.; Cirino, G.; Del Soldato, P.; Ongini, E. Gastric tolerability and prolonged prostaglandin inhibition in the brain with a nitric oxide-releasing flurbiprofen derivative, NCX-2216 [3-[4-(2-fluoro-R-methyl-[1,1′-biphenyl]-4- acetyloxy)-3-methoxyphenyl]-2-propenoic acid 4-nitrooxybutyl ester] J. Pharmacol. Exp. Ther. 2004, 309, 626-633 (Pubitemid 38542616)
30. Abdellatif, K. R. A.; Chowdhury, M. A.; Dong, Y.; Chen, Q. H.; Knaus, E. E. Diazen-1-ium-1,2-diolated and nitrooxyethyl nitric oxide donor ester prodrugs of anti-inflammatory (E)-2-(aryl)-3-(4-methanesulfonylphenyl)acrylic acids: synthesis, cyclooxygenase inhibition, and nitric oxide release studies Bioorg. Med. Chem. 2008, 16, 3302-3308 (Pubitemid 351418176)
31. Csont, T.; Ferdinandy, P. Cardioprotective effects of glyceryl trinitrate: beyond vascular nitrate tolerance Pharmacol. Ther. 2005, 105, 57-68 (Pubitemid 40038870)
32. Fung, H. L.; Bauer, J. A. Mechanisms of nitrate tolerance Cardiovasc. Drugs Ther. 1994, 8, 489-499 (Pubitemid 24239716)
33. Chakrapani, H.; Showalter, B. M.; Citro, M. L.; Keefer, L. K.; Saavedra, J. E. Nitric oxide prodrugs: diazeniumdiolate anions of hindered secondary amines Org. Lett. 2007, 9, 4551-4554
34. Reid, J. M.; Stobaugh, J. F.; Sternson, L. A. liquid chromatographic determination of cyclophosphamide enantiomers in plasma by precolumn chiral derivatization Anal. Chem. 1989, 61, 441-446 (Pubitemid 19068942)
35. 2NHOH (n = 1, 2, 3) Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1978, 33, 574
36. Uddin, M. J.; Rao, P. N. P.; McDonald, R.; Knaus, E. E. A New Class of Acyclic 2-Alkyl-1,1,2-triaryl (Z)-Olefins as Selective Cyclooxygenase-2 Inhibitors J. Med. Chem. 2004, 47, 6108-6111 (Pubitemid 39507352)
37. Winter, C. A.; Risley, E. A.; Nuss, G. W. Carrageenin-induced edema in hind paw of rat as an assay for antiinflammatory drugs Proc. Soc. Exp. Biol. Med. 1962, 111, 544-547
38. 2-alkyl-1- (pyrrolidin-1-yl)diazen-1-ium-1,2-diolate 4-aryl(heteroaryl)-1,4-dihydro-2,6- dimethyl-3-nitropyridine-5-carboxylates Drug Dev. Res. 2003, 60, 204-216 (Pubitemid 37351792)
39. Cocco, M. T.; Congiu, C.; Onnis, V.; Morelli, M.; Cauli, O. Synthesis of ibuprofen heterocyclic amides and investigation of their analgesic and toxicological properties Eur. J. Med. Chem. 2003, 38, 513-518 (Pubitemid 36588917)