Synthesis and MAO-B substrate properties of 1-methyl-4-heteroaryl-1,2,3,6-tetrahydropyridines

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 2, 1999, Pages 231-239

  Yu, Jian ^a   Castagnoli Jr , Neal ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; NEUROTOXIN; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENZYME ACTIVITY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE; KINETICS; MODELS, CHEMICAL; MONOAMINE OXIDASE; SPECTROPHOTOMETRY;

EID: 0032976701     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)00201-6     Document Type: Article

References (31)

1. Langston, J. W.; Irwin, I.; Langston, E. B.; Forno, L. S. Science 1984, 225, 1480.
2. Heikkila, R. E.; Hess, A.; Duvoisin R. C. Science 1984, 224, 1451.
3. Chiba, K.; Trevor, A.; Castagnoli, N. Jr. Biochem. Biophys. Res. Commun. 1984, 120, 574.
4. Gessner, W.; Brossi, A.; Shen, R.-S.; Fritz, R. R.; Abell, C. W. Helv. Chim. Acta. 1984, 67, 2037.
5. Markey, S. P.; Johannessen, J. N.; Chiueh, C. C.; Burn, R. S.; Herkenham, M. A. Nature (London) 1984, 311, 464.
6. Wang, Y.-X.; Mabic, S.; Castagnoli, N. Jr. Bioorg. Med. Chem. 1998, 6, 143.
7. Ottoboni, S.; Caldera, P.; Trevor, A.; Castagnoli, N. Jr. J. Biol. Chem. 1989, 264, 13684.
8. Silverman, R. B. Acc. Chem. Res. 1995, 28, 335.
9. Silverman, R. B. Electron transfer chemistry of monoamine oxidase. In Advances in Electron Transfer Chemistry; Mariano, P. S., Ed.; JAI: Greenwich, 1992; Vol. 2, pp 177-213.
10. Silverman, R. B.; Zhou, J. P.; Eaton, P. E. J. Am. Chem. Soc. 1993, 115, 8841.
11. Zhong, B.; Silverman, R. B. J. Am. Chem. Soc. 1997, 119, 6690.
12. (a) Maeda, Y.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 328.
13. (b) Musa, O. M.; Horner, J. H.; Shahin, H.; NewComb, M. J. Am. Chem. Soc. 1996, 118, 3862.
14. Nimkar, S. K.; Anderson, A. H.; Rimoldi, J. M.; Stanton, M.; Castagnoli, K. P.; Mabic, S.; Wang, Y.-X.; Castagnoli, N. Jr. Chem. Res. Toxicol. 1996, 9, 1013.
15. Hall, L.; Murray, S.; Castagnoli, K.; Castagnoli, N. Jr. Chem. Res. Toxicol. 1992, 5, 625.
16. Palmer, S. L.; Mabic, S.; Castagnoli, N. Jr. J. Med. Chem. 1997, 40, 1982.
17. Anderson, A. H.; Kuttab, S.; Castagnoli, N. Jr. Biochemistry 1996, 35, 3335.
18. Rimoldi, J. M.; Wang, Y.-X.; Nimkar, S. K.; Kuttab, S. H.; Anderson, A. H.; Burch, H.; Castagnoli, N. Jr. Chem. Res. Toxicol. 1995, 8, 703.
19. Franot, C.; Mabic, S.; Castagnoli, N. Jr. Bioorg. Med. Chem. 1997, 5, 1519.
20. Walker, M. C.; Edmondson, D. E. Biochemistry 1994, 33, 7088.
21. Yongster, S. K.; Mackeown, K. A.; Jin, Y.-Z.; Ramsay, R. R.; Heikkila, R. E.; Singer, T. P. J. Neurochem. 1989, 53, 1837.
22. Zhao, Z. Y.; Dalvie, D.; Naiman, N.; Castagnoli, K. P.; Castagnoli, N. Jr. J. Med. Chem. 1992, 35, 4473.
23. Anderson, A. H. PhD Dissertation, Virginia Polytechnic Institute and State University, 1997, p 86.
24. Kondo, K.; Matsumoto, M. Chemistry Letters 1974, 701.
25. Ichimura, K.; Ichikawa, S.; Imamura, K. Bull. Chem. Soc. Jpn. 1976, 49, 1157.
26. Jones, R. A. Pyrroles Part One: The Synthesis and the Physical and Chemical Aspects of the Pyrrole Ring; Wiley & Sons: New York, 1990; Vol. 48, pp 296-302.
27. Stetter, H.; Krassett, J. Heterocyclic Chem., 1977, 14, 573.
28. Kruse, C. G.; Bouw, J. P.; Van Hes R.; Van De Kuilen, A.; Den Hartog, J. A. J. Heterocycles 1987, 26, 3141.
29. Pitts, S. M.; Markey, S. P.; Murphy, D. L.; Weisz, A. In MPTP-A Neurotoxin Producing a Parkinsonian Syndrome; Academic: New York, 1986; pp 703-716.
30. Salach, J. I.; Weyler, W. Methods Enzymol. 1987, 142, 627.
31. Tipton, K. F.; Singer, T. P. J. Neurochem. 1993, 61, 1191.