Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 7, 2004, Pages 1799-1802

  Davies, Huw M L ^a   Hopper, Darrin W ^a   Hansen, Tore ^a   Liu, Quixu ^b   Childers, Steven R ^b  

^a UNIVERSITY AT BUFFALO   (United States)

^b WAKE FOREST SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CARBON; CARBONYL DERIVATIVE; DOPAMINE TRANSPORTER; METHYLPHENIDATE; N TERT BUTYLOXYCARBONYLPIPERIDINE; N TERT BUTYLOXYCARBONYLPYRROLIDINE; PROTON; RHODIUM; RHODIUM DERIVATIVE; RHODIUM TETRAACETATE; SEROTONIN TRANSPORTER; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; CATALYST; DEPROTECTION REACTION; DRUG BINDING; DRUG BINDING SITE; DRUG MECHANISM; DRUG SELECTIVITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

BINDING SITES; CARRIER PROTEINS; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; MEMBRANE GLYCOPROTEINS; MEMBRANE TRANSPORT PROTEINS; METHYLPHENIDATE; NERVE TISSUE PROTEINS; PROTEIN BINDING; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS;

INSERTION SEQUENCES;

EID: 1542613869     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.12.097     Document Type: Article

References (29)

1. Perel J., Dayton P. Methylphenidate. 1976;Marcel Decker, New York.
2. Diller L.H. Hastings Center Rep. 26:1996;1201.
3. Khantzian E.J., Gawin F., Kleber H.D., Riordan C.E. J. Subst. Abuse Treat. 1:1984;107.
4. Gawin F., Riordan C., Kleber H. Am. J. Drug Alcohol Abuse. 11:1985;193.
5. Levin F.R., Evans S.M., McDowell D.M., Kleber H.D. J. Clin. Psychiatry. 59:1998;300.
6. Wayment H.K., Deutsch H., Schweri M.M., Schenk J.O. J. Neurochem. 72:1999;1266.
7. Froimowitz M., Deutsch H.M., Shi Q., Wu K.M., Glaser R., Adin I., George C., Schweri M.M. Bioorg. Med. Chem. Lett. 7:1997;1213.
8. Deutsch H.M., Shi Q., Gruszecka-Kowalik E., Schweri M.M. J. Med. Chem. 39:1996;1201.
9. Axten J.M., Krim L., Kung H.F., Winkler J.D. J. Org. Chem. 63:1998;9628.
10. Gatley S.J., Pan D.F., Chen R.Y., Chaturvedi G., Ding Y.S. Life Sci. 58:1996;L231.
11. Deutsch H.M. Med. Chem. Res. 8:1998;91.
12. Deutsch H.M., Collard D.M., Zhang L.A., Burnham K.S., Deshpande A.K., Holtzman S.G., Schweri M.M. J. Med. Chem. 42:1999;882.
13. Meltzer P.C., Wang P., Blundell P., Madras P.K. J. Med. Chem. 46:2003;1538.
14. Patrick K.S., Caldwell R.W., Ferris R.M., Breese G.R. J. Pharmacol. Exp. Ther. 241:1987;152.
15. Szporny K., Gorog P. Biochem. Pharmacol. 8:1961;263.
16. Prashad M., Liu Y.G., Kim H.Y., Repic O., Blacklock T.J. Tetrahedron: Asymmetry. 10:1999;3479.
17. Thai D.L., Sapko M.T., Reiter C.T., Bierer D.E., Perel J.M. J. Med. Chem. 41:1998;591.
18. Matsumura Y., Kanda Y., Shirai K., Onomura O., Maki T. Org. Lett. 1:1999;175.
19. Matsumura Y., Kanda Y., Shirai K., Onomura O., Maki T. Tetrahedron. 56:2000;7411.
20. Davies H.M.L., Matasi J.J., Hodges L.M., Huby N.J.S., Thornley C., Kong N., Houser J.H. J. Org. Chem. 62:1997;1095.
21. Davies H.M.L., Gilliatt V., Kuhn L.A., Saikali E., Ren P., Hammond P.S., Sexton T., Childers S.R. J. Med. Chem. 44:2001;1509.
22. Davies H.M.L., Stafford D.G., Hansen T. Org. Lett. 1:1999;233.
23. Davies H.M.L., Gregg T.M. Tetrahedron Lett. 43:2002;4951.
24. Davies H.M.L. Eur. J. Org. Chem. 10:1999;2459.
25. Davies H.M.L., Venkataramani C., Hansen T., Hopper D.W. J. Am. Chem. Soc. 125:2003;6462.
26. Davies H.M.L., Hansen T., Hopper D.W., Panaro S.A. J. Am. Chem. Soc. 121:1999;6509.
27. Axten J.M., Ivy R., Krim L., Winkler J.D. J. Am. Chem. Soc. 121:1999;6511.
28. Deutsch H.M., Dunn T., Ye X.C., Schweri M.M. Med. Chem. Res. 9:1999;213.
29. Bennett B.A., Wichems C.H., Hollingsworth C.K., Davies H.M.L., Thornley C., Sexton T., Childers S.R. J. Pharmacol. Exp. Ther. 272:1995;1176.