Nitroaromatic amino acids as inhibitors of neuronal nitric oxide synthase

Journal of Medicinal Chemistry

Volumn 41, Issue 14, 1998, Pages 2636-2642

  Cowart, Marion ^a   Kowaluk, Elizabeth A ^a   Daanen, Jerome F ^a   Kohlhaas, Kathy L ^a   Alexander, Karen M ^a   Wagenaar, Frank L ^a   Kerwin Jr , James F ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROARYL AMINO ACID DERIVATIVE; AROMATIC NITRO COMPOUND; N METHYL DEXTRO ASPARTIC ACID; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DRUG INHIBITION; ENANTIOMER; ENZYME INHIBITION; ENZYME KINETICS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SYNTHESIS;

ACETYLCHOLINE; ANIMALS; CEREBELLUM; CYCLIC GMP; ENDOTHELIUM, VASCULAR; ENZYME INHIBITORS; ISOENZYMES; KINETICS; MUSCLE RELAXATION; NEURONS; NITRIC OXIDE SYNTHASE; NITRO COMPOUNDS; ORNITHINE; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032474779     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980073h     Document Type: Article

References (19)

1. Kerwin, J. F., Jr.; Lancaster, J. R., Jr.; Feldman, P. L. Nitric oxide: A new paradigm for second messengers. J. Med. Chem. 1995, 38, 4343-4362.
2. (a) Feldman, P. L.; Griffith, O. W.; Stuehr, D. J. The surprising life of nitric oxide. C&E News 1993, Dec 20, 26-38.2.
3. (b) Marletta, M. A. Approaches toward selective inhibition of nitric oxide synthase. J. Med. Chem. 1994, 37, 1899-1907.
4. (a) Schuman, E. M.; Madison, D. V. A requirement for the intercullular messenger nitricoxide in long-term potentiation. Science 1991, 254, 1503-1506.
5. (b) Wilson, R. I.; Yanovsky, J.; Gödecke, A.; Stevens, D. R.; Schrader, J.; Haas, H. L. Endothelial nitric oxide synthase and LTP. Science 1991, 254, 1503-1506.
6. Holscher, C.; Rose, S. P. R. An inhibitor of nitric oxide synthesis prevents memory formation in the chick. Neurosci. Lett. 1992, 145, 165-167.
7. Beckman, J. S. The double-edged role of nitric oxide in brain function and superoxide-mediated injury. J. Dev. Phys. 1991, 15, 53-59.
8. O'Dell, T. J.; Huang, P. L.; Dawson, T. M.; Dinerman, J. L.; Snyder, S. H.; Kandel, E. R.; Fishman, M. C. Endothelial NOS and the blockade of LTP by NOS inhibitors in mice lacking neuronal NOS. Science 1994, 265, 542-546.
9. Huang, Z.; Huang, P. L.; Panahian, N.; Daldara, T.; Fishman, M. C.; Moskowitz, M. A. Effects of cerebral ischemia in mice deficient in neuronal nitric oxide synthase. Science 1994, 265, 1883-1885.
10. ω-nitroarginine and phenylalanine-containing dipeptides and dipeptide esters. J. Med. Chem. 1997, 40, 2813-2817.
11. ω-propyl arginine. J. Med. Chem. 1997, 40, 3869-3870.
12. (c) Shankaran, K.; Donnelly, K. L.; Shah, S. K.; Humes, J. L.; Pacholok, S. G.; Grant, S. K.; Green, B. G.; MacCoss, M. Inhibition of nitric oxide synthase by benzolazolones. Bioorg. Med. Chem. Lett. 1997, 7, 2887-2892.
13. Babbedge, R. C.; Bland-Ward, P. A.; Hart, S. L.; Moore, P. K. Inhibition of rat cerebellar nitric oxide synthase by 7-nitroindazole and related substituted indazoles. Br. J. Pharmacol. 1993, 110, 225-228.
14. 5-hydroxy-L-ornithine derived siderophore-carbacephalosporin B-lactam conjugates: Iron transport mediated drug delivery. J. Med. Chem. 1990, 33, 461-464.
15. Garthwaite, J.; Charles, S. L.; Chess-Williams, R. Endothelium-derived relaxing factor release on activation of NMDA receptors suggests role as intercellular messenger in the brain. Nature 1988, 336, 385.
16. Bredt, D. S.; Snyder, S. H. Nitric oxide mediates glutamate-linked enhancement of cGMP levels in the cerebellum. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9030-9033.
17. Ignarro, L. J.; Harrison, R. G.; Wood, K. S.; Kadowitz, P. J. Activation of purified soluble guanylate cyclase by endothelium-derived relaxing factor from intrapulmonary artery and vein: stimulation by acetylcholine, bradykinin, and arachidonic acid. J. Pharmacol. Exp. Ther. 1986, 237, 893-900.
18. Palmer, R. M. J.; Ferrige, A. G.; Moncada, S. Nitric oxide release accounts for the biological activity of endothelium-derived relaxing factor. Nature 1987, 327, 524-526.
19. Pollock, J. S.; Forstermann, U.; Mitchell, J. A.; Warner, T. D.; Schmidt, H. H. H. W.; Nakane, M.; Murad, F. Purification and characterization of particulate endothelium-derived relaxing factor synthase from cultured and native bovine aortic endothelial cells. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10480-10484.