Synthesis and pharmacological evaluation of (Z)-9-(Heteroarylmethylene)-7-azatricyclo[4.3.1.03,7]decanes: Thiophene analogues as potent norepinephrine transporter inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 20, 2003, Pages 3565-3569

  Zhou, Jia ^a   Kläß, Thomas ^a   Zhang, Ao ^a   Johnson, Kenneth M ^b   Wang, Cheng Z ^b   Ye, Yanping ^b   Kozikowski, Alan P ^a  

^a GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

^b University of Texas Medical Branch School of Medicine   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AROMATIC COMPOUND; ATOMOXETINE; DECANE; DESIPRAMINE; DOPAMINE; NORADRENALIN; NORADRENALIN TRANSPORTER INHIBITOR; PYRIDINE DERIVATIVE; RECEPTOR BLOCKING AGENT; SEROTONIN; THIOPHENE DERIVATIVE; TROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATECHOLAMINE UPTAKE; CONFORMATIONAL TRANSITION; DRUG ACTIVITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; EVALUATION; HUMAN; INHIBITION KINETICS; STRUCTURE ACTIVITY RELATION;

EID: 0141516705     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00786-8     Document Type: Article

References (34)

1. Pacholczyk T., Blakely R.D., Amara S.G. Nature. 350:1991;350.
2. Barker, E. L.; Blakely, R. D. In Psychopharmacology. A Fourth Generation of Progress; Bloom, F. E., Kupfer, D. J., Eds.; Raven: New York, 1995; p 321.
3. Zavosh A., Schaefer J., Ferrel A., Figlewicz D.P. Brain Res. Bull. 49:1999;291.
4. Southwick S.M., Bremner J.D., Rasmusson A., Morgan C.A., Arnsten A., Charney D.S. Biol. Psychiatry. 46:1999;1192.
5. Versiani M., Cassano G., Perugi G., Benedetti A., Mastalli L., Nardi A., Savino M. J. Clin. Psychiatry. 63:2002;31.
6. Biederman J., Spencer T. Biol. Psychiatry. 46:1999;1234.
7. Van Moffaert M., Dierick M. CNS Drugs. 12:1999;293.
8. Fleishaker J.C. Clin. Pharmacokinet. 39:2000;413.
9. Blier P. J. Psychiatry Neurosci. 26 (Suppl.), S1:2001.
10. Davids E., Zhang K., Tarazi F.I., Baldessarini R.J. Brain Res. Rev. 42:2003;1.
11. Bymaster F.P., Katner J.S., Nelson D.L., Hemrick-Luecke S.K., Threlkeld P.G., Heiligenstein J.H., Morin S.M., Gehlert D.R., Perry K.W. Neuropsychopharmacology. 27:2002;699.
12. Michelson D., Adler L., Spencer T., Reimherr F.W., West S.A., Allen A.J., Kelsey D., Wernicke J., Dietrich A., Milton D. Biol. Psychiatry. 53:2003;112.
13. Trendelenburg U. Trends Pharmacol. Sci. 12:1991;334.
14. Amara S.G., Sonders M.S. Drug Alcohol Depend. 51:1998;87.
15. Tellioglu, T.; Robertson, D. Exp. Rev. Mol. Med. 2001, 19 November ( http://www-ermm.cbcu.cam.ac.uk/01003878h. htm) .
16. Junquera E., Romero J.C., Aicart E. Langmuir. 17:2001;1826.
17. Smith M.P., Hoepping A., Johnson K.M., Trzcinska M., Kozikowski A.P. Drug Discov. Today. 4:1999;322.
18. Carroll F.I., Howell L.L., Kuhar M.J. J. Med. Chem. 42:1999;2721.
19. Singh S. Chem. Rev. 100:2000;925.
20. Froimowitz M. J. Comput. Chem. 14:1993;934.
21. Petukhov P.A., Zhang J., Kozikowski A.P., Wang C.Z., Ye Y.P., Johnson K.M., Tella S.R. J. Med. Chem. 45:2002;3161.
22. Hoepping A., Johnson K.M., George C., Flippen-Anderson J., Kozikowski A.P. J. Med. Chem. 43:2000;2064.
23. Zhang A., Zhou G.C., Hoepping A., Mukhopadhyaya J., Johnson K.M., Zhang M., Kozikowski A.P. J. Med. Chem. 45:2002;1930.
24. Zhang A., Zhou G.C., Rong S.-B., Johnson K.M., Zhang M., Kozikowski A.P. Bioorg. Med. Chem. Lett. 12:2002;993.
25. Zhou J., Zhang A., Kläß T., Johnson K.M., Wang C.Z., Ye Y.P., Kozikowski A.P. J. Med. Chem. 46:2003;1997.
26. Patani G.A., LaVoie E.J. Chem. Rev. 96:1996;3158.
27. Gohlke H., Gundisch D., Schwarz S., Seitz G., Tilotta M.C., Wegge T. J. Med. Chem. 45:2002;1064.
28. Hoyte R.M., Zhang J., Lerum R., Oluyemi A., Persaud P., O'Connor C., Labaree D.C., Hochberg R.B. J. Med. Chem. 45:2002;5397.
29. 2S: C 59.34, H 5.60, N 4.33; found: C 59.19, H 5.57, N 4.43.
30. Dondoni A., Mastellari A.R., Medici A., Negrini E., Pedrini P. Synthesis. 1986;757.
31. Minnis W. Org. Synth. II:1943;357. (Coll. Vol.).
32. Slusher B.S., Tiffany C.W., Olkowski J.L., Jackson P.F. Drug Alcohol Depend. 48:1997;43.
33. Wang S., Sakamuri S., Enyedy I.J., Kozikowski A.P., Deschaux O., Bandyopadhyay B.C., Tella S.R., Zaman W.A., Johnson K.M. J. Med. Chem. 43:2000;351.
34. Bymaster F.P., Gehlert D., Nelson D., Threlkeld P., Hemrick-Luecke S., Katner J., Heiligenstein J., Morin S.M., Wong D.T., Perry K. Euro. Neuropsychopharmacol. 12:2002;418.