Synthesis and evaluation of the anticonvulsant activity of a series of 2-amino-1-phenyl-1-propranols derived from the metabolites of the antidepressant bupropion

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 1, 1997, Pages 1-6

  Musso, David L ^a,b   Mehta, Nariman B ^a   Soroko, Francis E ^a  

^a Burroughs Wellcome Co   (United States)

^b GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 TERT BUTYLAMINO 1 (3 CHLOROPHENYL)PROPANOL; 2 TERT BUTYLAMINO 1 (3 TRIFLUOROMETHYLPHENYL)PROPANOL; ANTICONVULSIVE AGENT; PHENYLPROPANOLAMINE DERIVATIVE; PHENYTOIN; PROPANOLAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRIC SHOCK; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTRAPERITONEAL DRUG ADMINISTRATION; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0031023672     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00577-X     Document Type: Article

References (20)

1. Schroeder, D. H. J. Clin. Psychiat. 1983, 44, 79.
2. Pitts, F. N. Jr. J. Clin. Psychiat. 1983, 44, (whole issue).
3. Musso, D. L.; Mehta, N. B.; Soroko, F. E.; Ferris, R. M.; Hollingsworth, E. B.; Kenney, B. T. Chirality 1993, 5, 495.
4. Kent, R. E.; McElvain, S. M. In Organic Synthesis; Horning, E. C., Ed.; John Wiley: New York, 1955; Coll. Vol. 4, pp 490-492.
5. Krynitsky, J. A.; Carhart, H. W. In Organic Synthesis; Rabjohn, N., Ed.; John Wiley: New York, 1963; Coll. Vol. 4, pp 436-438.
6. Kharasch, M. S.; Reinmuth, O. Grignard Reactions of Nonmetallic Substances; Prentice-Hall: New York, 1954; pp 767-845.
7. Mehta, N. B. U. S. patent 3,819,706.
8. Pasaribu, S. J.; Williams, L. R. Aust. J. Chem. 1973, 26, 1327.
9. Mehta, N. B.; Musso D. L. J. Pharm. Sci. 1986, 75, 410.
10. Elemental analyses were performed on all compounds and are within ±0.4% of the calculated values. All compounds were analyzed by NMR spectroscopy and are consistent with the assigned structures.
11. Tucker, H. J. Org. Chem. 1979, 44, 2943.
12. Musso, D. L.; Mehta, N. B. J. of Liquid Chromatography 1981, 4, 1417.
13. Topliss, J. G. J. Med Chem. 1972, 15, 1006.
14. Woodbury, L. A.; Davenport, V. D. Arch. Int. Pharmacodyn. Ther. 1952, 92, 97.
15. Mueller, H.K.; Mueller, E.; Baborowski, H. J. Prakt. Chem. 1971, 313, 1.
16. Lemberger, L.; Sernatinger, E.; Kuntzman, R. Biochem.Pharmacol. 1970, 19, 3021.
17. Mehta, N. B.; Diuguid, C. A.; Soroko, F. E. J. Med Chem. 1981, 24, 465.
18. Koshinaka, E.; Kurata, S.; Yamagishi, K.; Kubo, S.; Kato, H. Chem. Abstr. 1979, 90, 132710.
19. Ramcharitar, V.; Levine, D. S.; Goldberger, B. A.; Caplan, Y.H. Chem. Abstr. 1993, 118, 93818.
20. Butz, R. F.; Welch, R. M.; Findlay, J. W. A. J. Pharmacol. Exp. Ther. 1982, 221, 676.