Synthesis and neurotoxic potential of racemic and chiral dihydroxytetrahydroquinoline derivatives

Tetrahedron

Volumn 56, Issue 30, 2000, Pages 5345-5352

  Lewis, Russell J ^a   Francis, Charles A ^b   Lehr, Roland E ^b   Leroy Blank, C ^b  

^a CIVIL AEROSPACE MEDICAL INSTITUTE   (United States)

^b UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

Asymmetry; Catecholamines; Cyclization; Indoleamines

Indexed keywords

3 AMINO 6,7 DIHYDROXY 1,2,3,4 TETRAHYDROQUINOLINE; 3 AMINO 6,8 DIHYDROXY 1,2,3,4 TETRAHYDROQUINOLINE; 3 AMINOMETHYL 6,7 DIHYDROXY 1,2,3,4 TETRAHYDROQUINOLINE; DIHYDROXYTETRAHYDROQUINOLINE DERIVATIVE; DOPAMINE; NEUROTOXIN; NORADRENALIN; QUINOLINE DERIVATIVE; SEROTONIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; CYCLIZATION; DOPAMINE BRAIN LEVEL; ENANTIOMER; HYDROGENATION; MOUSE; NEUROTOXICITY; NONHUMAN; NORADRENALIN BRAIN LEVEL; PRIORITY JOURNAL; RACEMIC MIXTURE; SEROTONIN BRAIN LEVEL; STOICHIOMETRY; SYNTHESIS; TOXICITY TESTING;

EID: 0034698187     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00470-1     Document Type: Article

References (21)

1. Blank C.L., Lewis R.J., Lehr R.E. 6-Hydroxydopamine and Related Catecholaminergic Neurotoxins: Molecular Mechanisms. Kostrzewa R.M. Highly Selective Neurotoxins: Basic and Clinical Applications. 1998;1-8 Humana Press, Totowa, NJ.
2. Lew R., Malberg J.E., Ricuarte G.A., Seiden L.S. Evidence For and Mechanism of Action of Neurotoxicity of Amphetamine Related Compounds. Kostrzewa R.M. Highly Selective Neurotoxins: Basic and Clinical Applications. 1998;235-268 Humana Press, Totowa, NJ.
3. Royland J.E., Langston J.W. MPTP: a Dopaminergic Neurotoxin. Kostrzewa R.M. Highly Selective Neurotoxins: Basic and Clinical Applications. 1998;141-194 Humana Press, Totowa, NJ.
4. Bloem B.R., Irwin I., Buruma O.J.S., Haan J., Roos R.A.C., Tetrud J.W., Langston J.W. J. Neurol. Sci. 97:1990;273-293.
5. Youdim M.B.H., Lavie L. Life Sci. 55:1994;2077-2082.
6. Saxena A.K., Jain P.C., Anand N. Indian J. Chem. 13:1975;230-237.
7. Jones G. Quinolines. Part I. Jones G. The Chemistry of Heterocyclic Compounds. 1997;207-220 Wiley, New York.
8. Narang K.S., Ray J.N., Sachdeva T.D. J. Indian Chem. Soc. 13:1936;260-266.
9. Burk M.J. J. Am. Chem. Soc. 113:1991;8518-8519.
10. Burk M.J. Chem. Abstr. 118:1993;25118s.
11. O'Reilly N.J., Derwin W.S., Lin H.C. Synthesis. 7:1990;550-556.
12. Buckley T.F. III, Rapoport H. J. Am. Chem. Soc. 102:1980;3056-3062.
13. Irie H., Shiina A., Fushimi T., Katakawa J., Fujii N., Yajima H. Chem. Lett. 1980:1980;875-878.
14. Ma S., Lin L., Rhagavan R., Cohenour P., Lin P.Y.T., Bennet J., Lewis R.J., Kostrzewa R., Lehr R.E., Blank C.L. J. Med. Chem. 38:1995;4087-4097.
15. Baumgarten H.G., Bjorklund A., Lachenmayer L., Nobin A., Stenevi U. Acta Physiol. Scand. Suppl. 373:1971;1-15.
16. Herman Z.S., Bonczek A. Pharmacology. 17:1978;8-14.
17. Blank C.L., Murrill E., Adams R.N. Brain Res. 45:1972;635-637.
18. Blank C.L., Sasa S., Isernhagen R., Meyerson L.R., Wassil D., Wong P., Modak A.T., Stavinoha W.B. J. Neurochem. 33:1979;213-219.
19. Blank C.L., Abdullah H., Modak A.T., Stavinoha W.B. Microwave Heating and Serotonin Determinations. Blank C.L., Stavinoha W.B., Maruyama Y. Microwave Irradiation as a Tool to Study Labile Metabolites in Tissue. 1983;63-73 Pergamon, London.
20. Freeman K., Lin P.Y.T., Lin L., Blank C.L. Monoamines and Metabolites in the Brain. Holman R.B., Joseph M.H., Cross A.J. High Performance Liquid Chromatography in the Neurosciences, Monograph in the International Brain Research Organisation (IBRO) Handbook Series. 1993;27-55 Wiley, London.
21. Lin P.Y.T., Bulawa M.C., Wong P., Lin L., Scott J., Blank C.L. J. Liq. Chromatogr. 7:1984;509-538.