Conformationally restricted arginine analogues as inhibitors of human nitric oxide synthase

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 13, 1997, Pages 1763-1768

  Shearer, Barry G ^a   Lee, Shuliang ^a   Franzmann, Karl W ^b   White, Helen A R ^b   Sanders, Daniella C J ^b   Kiff, Rachel J ^c   Garvey, Edward P ^a   Furfine, Eric S ^a  

^a GLAXOSMITHKLINE   (United States)

^b Department of Medicinal Chemistry ^*  (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE DERIVATIVE; N(G) NITROARGININE METHYL ESTER; NITRIC OXIDE SYNTHASE INHIBITOR; ORNITHINE DERIVATIVE;

ARTHRITIS; ARTICLE; BLOOD PRESSURE REGULATION; DRUG CONFORMATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME SUBSTRATE; NERVE DEGENERATION; NEUROTRANSMITTER RELEASE; SEPTIC SHOCK;

EID: 0030761844     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00309-0     Document Type: Article

References (16)

1. Moncada, S.; Palmer, R.M.J.; Higgs, E.A. Pharmacol. Rev. 1991, 43, 109.
2. Marletta, M.A. J. Biol. Chem. 1993, 268, 12231.
3. Kerwin, J.F.; Heller, M. Med. Res. Rev. 1994, 14, 23.
4. (a) Garvey, E.P.; Oplinger, J.A.; Tanourey, G.J.; Sherman, P.A.; Fowler, M.; Marshall, S.; Harmon, M.F.; Paith, J.E.; Furfine, E.S. J. Biol. Chem. 1994, 269, 26669.
5. (b) Furfine, E.S.; Harmon, M.F.; Paith, J.E.; Knowles, R.G.; Salter, M.; Kiff, R.J.; Duffy, C.; Hazelwood, R.; Oplinger, J.A.; Garvey, E.P. J. Biol. Chem. 1994, 269, 26677.
6. (c) Garvey, E.P.; Oplinger, J.A.; Furfine, E.S.; Kiff, R.J.; Laszlo, F.; Whittle, B.J.R.; Knowles, R.G. J. Biol. Chem. 1997, 272, 4959.
7. O'Donnell, M.J.; Boniece, J.M.; Earp, S.E. Tetrahedron Lett. 1978, 2641.
8. S-Alkyl displacement by other amines proceeded efficiently by using only a slight excess of amine reagent.
9. Compounds 1-6 exhibit proton NMR, fast-atom bombardment mass spectroscopy, and elemental combustion analysis in agreement with assigned structures.
10. Shearer, B.G.; Oplinger, J.A.; Lee, S. Tetrahedron Lett. 1997, 38, 179.
11. (a) Miller, A.E.; Bischoff, J.J. Synthesis 1986, 777.
12. (b) Kim, K.; Yi-Tsong, L.; Mosher, H.S. Tetrahedron Lett. 1988, 29, 3183.
13. For experimental details of NOS inhibition assays see Reference 4a.
14. McMillan, K.; Masters, B.S.S. Biochemistry, 1993, 32, 9875.
15. eNOS-mediated relaxation of rat aortic rings was assayed according to Rees, D.D.; Palmer, R.M.J.; Hodson, H.F.; Moncada, S. Br. J. Pharmacol. 1989, 96, 418. iNOS-mediated relaxation of rat aortic rings was assayed according to Rees, D.D.; Celleck, S.; Palmer, R.M.J.; Moncada, S. Biochem. Biophys. Res. Commun. 1990, 173, 541.
16. eNOS-mediated relaxation of rat aortic rings was assayed according to Rees, D.D.; Palmer, R.M.J.; Hodson, H.F.; Moncada, S. Br. J. Pharmacol. 1989, 96, 418. iNOS-mediated relaxation of rat aortic rings was assayed according to Rees, D.D.; Celleck, S.; Palmer, R.M.J.; Moncada, S. Biochem. Biophys. Res. Commun. 1990, 173, 541.