Conformationally constrained no synthase inhibitors: Rigid analogs of L- N-iminoethylornithine

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 21, 1998, Pages 2961-2966

  Eustache, Jacques ^a,b   Grob, Alfred ^b   Lam, Charles ^b   Sellier, Odile ^a   Schulz, Gerhard ^b  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

^b Novartis Forschungsinstitut Wien ^*  (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

N(G) METHYLARGININE; N5 (1 IMINOETHYL)ORNITHINE; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE INHIBITOR; ORNITHINE DERIVATIVE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG CONFORMATION; DRUG SYNTHESIS; ENZYME INHIBITION; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ENZYME INHIBITORS; MOLECULAR CONFORMATION; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE TYPE II; ORNITHINE; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 0032212754     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00532-0     Document Type: Article

References (13)

1. 1. Palmer, R.M.J.: Ferriage, A.G., Moncada, S. Nature 1987, 327, 524.
2. 2. Few isosteric replacements of the α-aminoacid group have been reported : Hallinan, E.A.: Tsymbalov, S.; Finnegan, P.M.; Moore, W.M.; Jerome, G.M.; Currie, M.G.; Pitzele, B.S. J. Med. Chem. 1998, 41, 775.
3. G-butyl arginine. Stuehr, D.J.; Griffith, O.W. Adv. Enzymol Relat. Areas Mol. Biol. 1992, 65, 287.
4. 4. Schöllkopff, U.; Pettig, D.; Schulze, E.; Klinge, M.; Egert, E.; Benecke, B. and Noltemeyer, M. Angew. Chem. 1988, 700, 1238.
5. 5. Eustache, J. and Grob, A. Tetrahedron Lett. 1995, 36, 2045.
6. 6. For enzymic assays, the methyl esters 1-4 were converted to the corresponding free acids by acidic hydrolysis using aqueous HCl (6 M), 30 min.
7. 7. Ramsamy, K.; Olsen, R.K. and Emery, T. Synthesis 1982, 1, 42.
8. 8. Papandreou, G.; Tong, M.K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682.
9. 9. Guziec, Jr. F.S.; Wasmund, L.M. Tetrahedron Lett. 1990, 31, 23.
10. 10. Clarke, T.G.; Hampson, N.A.;.Lee, J.B.; Morley, J.R.; Scanlon, B. J. Chem. Soc. (C) 1970, 815.
11. 11. Nielsen, L.; Brehm, L.; Krogsgaard-Larsen, P. J. Med. Chem. 1990, 33, 71.
12. 12. Rosenkranz-Weiss, P.; Sessa, W.C.; Milstien, S.; Kaufman, S.; Watson, C.A.; Pober, J.S.. J. Clin. Invest. 1994, 93, 2236.
13. 50s are the mean of 3 independent experiments.