N-hydroxyurea and hydroxamic acid inhibitors of cyclooxygenase and 5- lipoxygenase

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 7, 1999, Pages 979-984

  Connolly, Peter J ^a   Wetter, Steven K ^a   Beers, Kimberly N ^a   Hamel, Stephanie C ^a   Chen, Robert H K ^a   Wachter, Michael P ^a   Ansell, Justin ^a   Singer, Monica M ^a   Steber, Michele ^a   Ritchie, David M ^a   Argentieri, Dennis C ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROPEROXY 6,8,11,14 ICOSATETRAENOIC ACID; 5 HYDROXYICOSATETRAENOIC ACID; ACETYLSALICYLIC ACID; ARACHIDONATE 5 LIPOXYGENASE; ARACHIDONIC ACID; ATRELEUTON; HYDROXAMIC ACID DERIVATIVE; HYDROXYUREA; ICOSANOID; INDOMETACIN; LEUKOTRIENE; LIPOXYGENASE INHIBITOR; NAPROXEN; PROSTAGLANDIN SYNTHASE; PROSTAGLANDIN SYNTHASE INHIBITOR; TEPOXALIN; UNCLASSIFIED DRUG; ZILEUTON;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BIOSYNTHESIS; DOG; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; INFLAMMATION; NONHUMAN; RAT;

ANIMALS; ARACHIDONATE 5-LIPOXYGENASE; CYCLOOXYGENASE INHIBITORS; DOGS; HYDROXAMIC ACIDS; HYDROXYUREA; LIPOXYGENASE INHIBITORS;

ANIMALIA; CANIS FAMILIARIS; SIGANUS;

EID: 0033526119     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00117-1     Document Type: Article

References (14)

1. 1. Moncada, S.; Flower, R. J.; Vane, J. R. In Goodman and Gilman's The Pharmacological Basis of Therapeutics, 7th ed.; Gilman, A. G., Goodman, L. S., Rall, T. W., Murad, F., Eds.; Macmillan: New York, 1985; pp 660-673.
2. 2. Prasit, P.; Riendeau, D. Ann. Rep. Med. Chem. 1997, 32, 211.
3. 3. Corey, E. J.; Cashman, J. R.; Kantner, S. S.; Wright, S. W. J. Am. Chem. Soc. 1984, 106, 1503.
4. 4. Summers, J. B.; Mazdiyasni, H.; Holms, J. H.; Ratajczyk, J. H.; Dyer, R. D.; Carter, G. W. J. Med. Chem. 1987, 30, 574.
5. 5. Jackson, W. P.; Islip, P. J.; Kneen, G.; Pugh, A.; Wates, P. J. J. Med. Chem. 1988, 31, 499.
6. 6. Summers, J. B.; Gunn, B. P.; Brooks, D. W. Preparation of N-hydroxy-N-(heteroarylalkyl)ureas and - carboxamides as lipoxygenase inhibitors. Eur. Pat. Appl. EP 279263.
7. 7. Brooks, C. D. W.; Stewart, A. O.; Basha, A.; Bhatia, P.; Ratajczyk, J. D.; Martin, J. G.; Craig, R. A.; Kolasa, T.; Bouska, J. B.; Lanni, C.; Harris, R. R.; Malo, P. E.; Carter, G. W.; Bell, R. L. J. Med. Chem. 1995, 38, 4768.
8. 8. Argentieri, D. C.; Ferro, M. P.; Ritchie, D. M.; Kirchner, T.; Wachter, M. P.; Anderson, D. W.; Rosenthale, M. E.; Capetola, R. J. J. Pharmacol. Exper. Ther. 1994, 271 1399.
9. 9 The carboxylic acid metabolite, RWJ 20142, inhibits COX but not 5-LO. Waldman, S. A.; Vitow, C.; Osborne, B.; Gillen, L.; Argentieri, D. C.; Wong, F. A.; Smith, I. L.; Chow, A.T.; Misiti, J.; Bjornsson, T. D. J. Clin. Pharmacol. 1996, 36, 462.
10. 1H NMR, 1R, and mass spectroscopy. Analytical purity of targets was determined by combustion analysis (C, H, N).
11. 11. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
12. 12. Stewart, A. O.; Brooks, D. W. J. Org. Chem. 1992, 57, 5020.
13. 50 = 6.6 μM (ECV-304 cells, n = 6).
14. 8