2-(iodoethenyl)benzylamines as potential probes for radical intermediates formed during monoamine oxidase catalyzed oxidations

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7357-7363

  Wang, Xueqing ^a   Silverman, Richard B ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 IODOETHENYL)BENZYL IODIDE; 2 (2 IODOETHENYL)BENZYLAMINE; MONOAMINE OXIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG CONFORMATION; DRUG OXIDATION; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME INHIBITION; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 0032538583     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980976i     Document Type: Article

References (27)

1. Strolin Benedetti, M.; Dosiert, P.; Tipton, K. F. Prog. Drug Metab. 1988,11, 149-174.
2. Woo, J. C. G.; Silverman, R. B. J. Am. Chem. Soc. 1995, 777, 1663-1664 and references therein.
3. Johnston, J. P. Biochem. Pharmacol. 1968, 17, 1285-1297.
4. Knoll, J. Med. Res. Rev. 1989, 12, 505-524.
5. Tetrud, V. W.; Längsten, J. W. Science 1989,245, 519-532.
6. (a) Silverman, R. B. Ace. Chem. Res. 1995, 28, 335-342.
7. (b) Silverman, R. B.; Zhou, J. J. P.; Ding, C. Z.; Lu, X. J. Am. Chem. Soc. 1995, 117, 12895-12896.
8. (a) Ottoboni, S.; Caldera, P.; Trevor, A.; Castagnoli, N., Jr. J. Biol. Chem. 1989, 264, 13684-13688.
9. (b) Walker, M. C.; Edmondson, D. E. Biochemistry 1994,33, 7088-7098.
10. Miller, J. R.; Edmondson, D. E.; Grissom, C. B. J. Am. Chem. Soc. 1995, 117, 7830-7831.
11. (a) Mann, C. K.; Barnes, K. K. Electrochemical Reactions in NonAqueous Systems; Marcel Dekker: New York, 1970; Chapter 9.
12. (b) Lewis, F. D.; Bassani, D. M.; Reddy, G. D. J. Org. Chem. 1993, 58, 6390-6393.
13. (a) Cohen, S. G.; Parola, A.; Parsons, G. H. Chem. Rev. 1973, 73, 141.
14. (b) Lewis, F. D.; Ho, T. J. Am. Chem. Soc. 1980, 102, 17511752.
15. Newcomb, M.; Tanaka, N.; Bouvier, A.; Tronche, C.; Homer, J. H.; Musa, O. M.; Martinez, F. N. J. Am. Chem. Soc. 1996,118,85058506.
16. (a) Hull, L. A.; Davis, G. T.; Rosenblatt, D. H. J. Am. Chem. Soc. 1969, 91, 6247.
17. (b) Lindsay Smith, J. R.; Mead, L. A. V. J. Chem. Soc., Perkin Trans. 2 1973, 206-210.
18. Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
19. Baldwin, J. E.; Cutting, J.; Dupont, W.; Kurse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736-738.
20. Austin, B. W.; Bilow, N.; Kelleghan, W. J.; Lau, K. S. J. Org. Chem. 1981, 46, 2280-2286.
21. Taber, D. F.; Wang, Y. J. Am. Chem. Soc. 1997, 119, 22-26.
22. Stock, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173-2174.
23. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981-987.
24. Holton, R. A.; Zoeller, J. R. J. Am. Chem. Soc. 1985,107,2124-2131.
25. Seyferth, D.; Heeren, J. K.; Singh, G.; Grim, S. 0.; Hughes, W. B. J. Organomet. Chem. 1966, 5, 267-274.
26. Weyler, W.; Salach, J. I. Arch. Biochem. Biophys. 1981, 212, 147-153.
27. Price, N. C.; Stevens, L. Fundamentals of Enzymology; Oxford University Press: Oxford, U.K., 1989, pp 178-179.