Synthesis and pharmacology of site-specific cocaine abuse treatment agents: The role of the phenyl group in highly modified methylphenidate analogs as dopamine uptake inhibitors

Medicinal Chemistry Research

Volumn 9, Issue 4, 1999, Pages 213-222

  Deutsch, Howard M ^b   Dunn, Travis ^b   Ye, Xiaocong ^b   Schweri, Margaret M ^a  

^a MERCER UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

COCAINE; DOPAMINE TRANSPORTER; DOPAMINE UPTAKE INHIBITOR; METHYLPHENIDATE; PHENYL GROUP;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL REACTION; DOPAMINE UPTAKE; DRUG ABUSE; DRUG BINDING; DRUG INHIBITION; DRUG POTENCY; DRUG SYNTHESIS; NONHUMAN; RAT; REACTION ANALYSIS;

EID: 0032859080     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Rouse, B.A. Trends in cocaine use in the general population. NIDA Research Monograph 1991, 110, 5-18. Also see; Rouse, B.A. Trends in cocaine use in the general population. Subst. Use Misuse 1997, 32, 1721-1726.
2. Rouse, B.A. Trends in cocaine use in the general population. NIDA Research Monograph 1991, 110, 5-18. Also see; Rouse, B.A. Trends in cocaine use in the general population. Subst. Use Misuse 1997, 32, 1721-1726.
3. National Household Survey on Drug Abuse: Population Estimates 1990. DHHS Pub. No. (ADM) 91-1732. Washington D.C., 1991, pp. 29-39, 59-63, and 111-115.
4. Ritz, M.C.; Lamb, R.J.; Goldberg, S.R.; Kuhar, M.J. Cocaine receptors on dopamine transporters are related to self-administration of cocaine. Science 1987, 237, 1219-1223.
5. Bergman J.; Madras, B.K.; Johnson, S.E.; Spealman, R.D. Effects of cocaine and related drugs in nonhuman primates. III. Self administration by squirrel monkeys. J. Pharmacol. Exp. Ther. 1989, 219, 150-155.
6. Kuhar, M.J.; Ritz, M.C.; Boja, J.W. The dopamine hypothesis of the reinforcing properties of cocaine. Trends Neurosci. 1991, 14, 299-302.
7. Kitayama, S.; Dohi, T. Cellular and molecular aspects of monoamine neurotransmitter transporters. Jpn. J. Pharmacol. 1996, 72, 195-208.
8. Carroll, F.I.: Lewin, A.H.: Kuhar, M.J. Dopamine Transporter Uptake Blockers. Structure-Activity Relationships. In: Neurotranmitter transporters: Structure, function and regulation. 1996, edited by Reith, M.E.A., Humana Press, Totowa, 263-295.
9. a. Walsh, S.L.; Cunningham, K.A. Serotonergic mechanisms involved in the discriminative stimulus, reinforcing and subjective effects of cocaine. Psychopharmacol. 1997, 130, 41-58.
10. b.Keverline-Frantz, K.I.; Boja, J.W.; Kuhar, M.J.; Abraham, P.; Burgess, J.P.; Lewin, A.H.; Carroll, F.I. Synthesis and ligand binding of tropane ring analogues of paroxetine. J. Med. Chem. 1998, 41, 247-257.
11. c. Yeghiayan, S.K.; Kelley, A.E.; Kula, N.S.; Campbell, A.; Baldessarini, R.J. Role of dopamine in behavioral effects of serotonin microinjected into rat striatum. Pharmacol. Biochem. Behav. 1997, 56, 251-259.
12. d. Koch, S.; Galloway, M.P. MDMA induced dopamine release in vivo: Role of endogenous serotonin. J. Neural Transm. 1997, 104, 135-146.
13. e. Rocha, B.A.; Scearce-Levie, K.; Lucas, J.J.; Hiroi, N.; Castanon, N.; Crabbe, J.C.; Nestler, E.J.; Hen, R. Increased vulnerability to cocaine in mice lacking the serotonin-1B receptor. Nature 1998, 393, 175-178.
14. Deutsch, H.M.; Shi, Q.; Gruszecka-Kowalik, E.; Schweri, M. M. Synthesis and pharmacology of potential cocaine antagonists .2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs. J. Med. Chem. 1996, 39, 1201-1209.
15. Froimowitz, M.; Deutsch, H.M.; Shi. Q.; Wu, K.M.; Glaser, R.; Adin, I.; George, C.; Schweri, M.M. Further evidence for a dopamine reuptake pharmacophore. The effect of N-methylation on threomethylphenidate and its analogs. Bioorg. Med. Chem. Lett. 1997, 7, 1213-1218.
16. Deutsch, H.M. Structure-activity relationships for methylphenidate analogs and comparisons to cocaine and tropanes. Medicinal Chemistry Research 1998, 8, 91-99.
17. Deutsch, H. M.; Schweri, M. M. Can stimulant binding and dopamine transport be differentiated? Studies with GBR 12783 derivatives. Life Sci. 1994, 55, PL115-PL120.
18. Deutsch, H. M.; Schweri, M. M.; Culbertson, C. T.; Zalkow, L. H. Synthesis and pharmacology of irreversible affinity labels as potential cocaine antagonist: aryl 1,4-dialkylpiperazines related to GBR-12783. Eur. J. Pharmacol. 1992, 220, 173-180.
19. Deutsch, H.M.; Collard, D.M.; Zhang, L.; Burnham, K.; Deshpande, A.K.; Holtzman, S.G.; Schweri, M.M. Synthesis and Pharmacology of Site-Specific Cocaine Abuse Treatment Agents: 2-(Aminomethyl)-3-phenylbicyclo[2.2.2] and [2.2.1]-alkanes Dopamine Uptake Inhibitors. J. Med. Chem. 1999, 41, 882-895.
20. Kozikowski, A.P.; Araldi, G.L.; Boja, J.; Meil, W.M.; Johnson, K.M.; Flippen-Anderson, J.L.; George, C.; Saiah, E. Chemistry and pharmacology of the piperidine-based analogues of cocaine. Identification of potent DAT inhibitors lacking the tropane skeleton. J. Med. Chem. 1998, 41, 1962-1969.
21. Carroll, F.I.; Lewin, A.H.; Boja, J.W.; Kuhar, M.J. Cocaine receptor: biochemical characterization and structure-activity relationships of cocaine analogs at the dopamine transporter. J. Med. Chem. 1992, 35, 969-981.
22. Ritz, M.C.; Cone, E.J.; Kuhar, M.J. Cocaine inhibition of ligand binding at dopamine, norepinephrine and serotonin transporters: a structure-activity study. Life Sci. 1990, 46, 635-645.
23. Madras, B.K.; Pristupa, Z.B.; Niznik, H.B.; Liang, A. Y.; Blundell, P.; Gonzalez, M. D.; Meltzer, P.C. Nitrogen-based drags are not essential for blockade of monoamine transporters. Synapse 1996 24, 340-348.
24. Meltzer, P.C.; Liang, A. Y.; Blundell, P.; Gonzalez, M.D.; Chen, Z.M.; George, C.; Madras, B.K. 2-carbomethoxy-3-aryl-8-oxabicyclo[3.2.1]octanes: Potent non-nitrogen inhibitors of monoamine transporters. J.Med.Chem. 1997 40, 2661-2673,.
25. Meltzer, P.C.; Blundell, P.; Madras, B.K. Structure activity relationships of inhibition of the dopamine transporter by 3-arylbicyclo[3.2.1]octanes. Med. Chem. Res. 1998, 8, 12-34.
26. Carroll, F.I., Mascarella, S.W., Kuzemko, M.A., Gao, Y., Abraham, P., Lewin, A.H., Boja, J.W., and Kuhar, M.J. Synthesis, ligand binding, and QSAR (CoMFA and classical) study of 3β-(3′-substituted phenyl)-, 3β-(4′-substituted phenyl)-, and 3β-(3′4′-disubstituted phenyl)tropane-2β-carboxylic acid methyl esters. J. Med. Chem. 1994, 37, 2865-2873.