Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for cocaine addiction

Journal of Medicinal Chemistry

Volumn 52, Issue 21, 2009, Pages 6768-6781

  Carroll, F Ivy ^a   Blough, Bruce E ^a   Abraham, Philip ^a   Mills, Andrew C ^a   Holleman, J Ashley ^a   Wolckenhauer, Scott A ^a   Decker, Ann M ^a   Landavazo, Antonio ^a   McElroy, K Timothy ^a   Navarro, Hernán A ^a   Gatch, Michael B ^b   Forster, Michael J ^b  

^a RTI INTERNATIONAL   (United States)

^b UNIVERSITY OF NORTH TEXAS HEALTH SCIENCE CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (N CYCLOPROPYLAMINO) 3 CHLOROPROPIOPHENONE; 2 (N TERT BUTYL) 3' CHLOROBUTANOPHENONE; 2 (N TERT BUTYL) 3' CHLOROHEXANOPHENONE; 2 (N TERT BUTYLAMINO) 3 CHLOROBUTANOPHENONE; AMFEBUTAMONE; DOPAMINE; DOPAMINE TRANSPORTER; NORADRENALIN; NORADRENALIN TRANSPORTER; SEROTONIN; SEROTONIN TRANSPORTER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; COCAINE DEPENDENCE; CONTROLLED STUDY; DRUG EFFICACY; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LOCOMOTION; MOUSE; NONHUMAN; RAT;

ADRENERGIC UPTAKE INHIBITORS; ANIMALS; BUPROPION; CELL LINE; COCAINE; COCAINE-RELATED DISORDERS; DISCRIMINATION LEARNING; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; DOPAMINE UPTAKE INHIBITORS; HUMANS; MICE; MOTOR ACTIVITY; NOREPINEPHRINE PLASMA MEMBRANE TRANSPORT PROTEINS; RADIOLIGAND ASSAY; RATS; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; SEROTONIN UPTAKE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 70449420106     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm901189z     Document Type: Article

References (61)

1. Substance Abuse and Mental Health Services Administration - Office of Applied Studies. Results from the 2007 National Survey on Drug Use and Health: National Findings. In Rockville, MD, 2008.
2. Herman, B. H.; Elkashef, A.; Vocci, F. Medications for the treatment of cocaine addiction: Emerging candidates. Drug Discovery Today: Therapeutic Strategies 2005, 2, 87-92. (Pubitemid 40932080)
3. Trudell, M. L.; Izenwasser, S. Dopamine transporters. Chemistry, biology, and pharmacology; John Wiley & Sons, Inc.: New York, 2008; Chapters 6-9, p 444.
4. Carroll, F. I.; Howard, J. L.; Howell, L. L.; Fox, B. S.; Kuhar, M. J. Development of the dopamine transporter selective RTI-336 as a pharmacotherapy for cocaine abuse. AAPS J. 2006, 8, E196-E203.
5. Runyon, S. P.; Carroll, F. I. Dopamine transporter ligands: recent developments and therapeutic potential. Curr. Top. Med. Chem. 2006, 6, 1825-1843.
6. Grabowski, J.; Shearer, J.; Merrill, J.; Negus, S. S. Agonist-like, replacement pharmacotherapy for stimulant abuse and dependence. Addict. Behav. 2004, 29, 1439-1464.
7. Howell, L. L.; Wilcox, K. M. The dopamine transporter and cocaine medication development: drug self-administration in nonhuman primates. J. Pharmacol. Exp. Ther. 2001, 298, 1-6.
8. Carroll, F. I.; Howell, L. L.; Kuhar, M. J. Pharmacotherapies for treatment of cocaine abuse: Preclinical aspects. J. Med. Chem. 1999, 42, 2721-2736.
9. Mello, N. K.; Negus, S. S. Preclinical evaluation of pharmacotherapies for treatment of cocaine and opioid abuse using drug self-administration procedures. Neuropsychopharmacology 1996, 14, 375-424.
10. Rothman, R. B.; Glowa, J. R. A review of the effects of dopaminergic agents on humans, animals, and drug-seeking behavior, and its implications for medication development. Mol. Neurobiol. 1995, 11, 1-19.
11. Mishra, M.; Kolhatkar, R.; Zhen, J.; Parrington, I.; Reith, M. E.; Dutta, A. K. Further structural optimization of cis-(6-benzhydrylpiperidin- 3-yl)-benzylamine and 1,4-diazabicyclo[3.3.1]nonane derivatives by introducing an exocyclic hydroxyl group: interaction with dopamine, serotonin, and norepinephrine transporters. Bioorg. Med. Chem. 2008, 16, 2769-2778.
12. Wilkes, S. The use of bupropion SR in cigarette smoking cessation. Int. J. Chron. Obstruct. Pulmon. Dis. 2008, 3, 45-53.
13. Tong, E. K.; Carmody, T. P.; Simon, J. A. Bupropion for smoking cessation. A review. Comprehensive Therapy 2006, 32, 26-33.
14. Hurt, R. D.; Sachs, D. P.; Glover, E. D.; Offord, K. P.; Johnston, J. A.; Dale, L. C.; Khayrallah, M. A.; Schroeder, D. R.; Glover, P. N.; Sullivan, C. R.; Croghan, I. T.; Sullivan, P. M. A comparison of sustained-release bupropion and placebo for smoking cessation. N. Engl. J. Med. 1997, 337, 1195-1202.
15. Fava, M.; Rush, A. J.; Thase, M. E.; Clayton, A.; Stahl, S. M.; Pradko, J. F.; Johnston, J. A. 15 years of clinical experience with bupropion HCl: from bupropion to bupropion SR to bupropion XL. Prim. Care Companion J. Clin. Psychiatry 2005, 7, 106-113.
16. Ascher, J. A.; Cole, J. O.; Colin, J. N.; Feighner, J. P.; Ferris, R. M.; Fibiger, H. C.; Golden, R. N.; Martin, P.; Potter, W. Z.; Richelson, E.; et al. Bupropion: A review of its mechanism of antidepressant activity. J. Clin. Psychiatry 1995, 56, 395-401.
17. Dhillon, S.; Yang, L. P.; Curran, M. P. Bupropion: a review of its use in the management of major depressive disorder. Drugs 2008, 68, 653-689.
18. Ferris, R. M.; Cooper, B. R. Mechanism of antidepressant activity of bupropion. J. Clin. Psychiatry Monogr. 1993, 11, 2-14.
19. Cryan, J. F.; Dalvi, A.; Jin, S. H.; Hirsch, B. R.; Lucki, I.; Thomas, S. A. Use of dopamine-beta-hydroxylase-deficient mice to determine the role of norepinephrine in the mechanism of action of antidepressant drugs. J. Pharmacol. Exp. Ther. 2001, 298, 651-657.
20. Li, S. X.; Perry, K. W.; Wong, D. T. Influence of fluoxetine on the ability of bupropion to modulate extracellular dopamine and norepinephrine concentrations in three mesocorticolimbic areas of rats. Neuropharmacology 2002, 42, 181-190.
21. Kelley, J. L.; Musso, D. L.; Boswell, G. E.; Soroko, F. E.; Cooper, B. R. (2S,3S,5R)-2-(3,5-Difluorophenyl)-3,5-dimethyl-2-morpholinol: A novel antidepressant agent and selective inhibitor of norepinephrine uptake. J. Med. Chem. 1996, 39, 347-349.
22. Nielsen, J. A.; Shannon, N. J.; Bero, L.; Moore, K. E. Effects of acute and chronic bupropion on locomotor activity and dopaminergic neurons. Pharmacol., Biochem. Behav. 1986, 24, 795-799.
23. Nomikos, G. G.; Damsma, G.; Wenkstern, D.; Fibiger, H. C. Effects of chronic bupropion on interstitial concentrations of dopamine in rat nucleus accumbens and striatum. Neuropsychopharmacology 1992, 7, 7-14.
24. Jones, C. N.; Howard, J. L.; McBennett, S. T. Stimulus properties of antidepressants in the rat. Psychopharmacology (Berl.) 1980, 67, 111-118.
25. Lamb, R. J.; Griffiths, R. R. Self-administration in baboons and the discriminative stimulus effects in rats of bupropion, nomifensine, diclofensine and imipramine. Psychopharmacology (Berl.) 1990, 102, 183-190.
26. Ortmann, R. The conditioned place preference paradigm in rats: effect of bupropion. Life Sci. 1985, 37, 2021-2027. (Pubitemid 16225807)
27. Tella, S. R.; Ladenheim, B.; Cadet, J. L. Differential regulation of dopamine transporter after chronic self-administration of bupropion and nomifensine. J. Pharmacol. Exp. Ther. 1997, 281, 508-513.
28. Spealman, R. D.; Madras, B. K.; Bergman, J. Effects of cocaine and related drugs in nonhuman primates. II. Stimulant effects on schedule-controlled behavior. J. Pharmacol. Exp. Ther. 1989, 251, 142-149.
29. Margolin, A.; Kosten, T. R.; Avants, S. K.; Wilkins, J.; Ling, W.; Beckson, M.; Arndt, I. O.; Cornish, J.; Ascher, J. A.; Li, S. H.; et al. A multicenter trial of bupropion for cocaine dependence in methadone- maintained patients. Drug Alcohol Depend. 1995, 40, 125-131.
30. Poling, J.; Oliveto, A.; Petry, N.; Sofuoglu, M.; Gonsai, K.; Gonzalez, G.; Martell, B.; Kosten, T. R. Six-month trial of bupropion with contingency management for cocaine dependence in a methadone-maintained population. Arch. Gen. Psychiatry 2006, 63, 219-228.
31. Newton, T. F.; Roache, J. D.; De La Garza, R.; Fong, T.; Wallace, C. L.; Li, S. H.; Elkashef, A.; Chiang, N.; Kahn, R. Bupropion reduces methamphetamine-induced subjective effects and cue-induced craving. Neuropsychopharmacology 2006, 31, 1537-1 544. (Pubitemid 43910448)
32. Elkashef, A. M.; Rawson, R. A.; Anderson, A. L.; Li, S. H.; Holmes, T.; Smith, E. V.; Chiang, N.; Kahn, R.; Vocci, F.; Ling, W.; Pearce, V. J.; McCann, M.; Campbell, J.; Gorodetzky, C.; Haning, W.; Carlton, B.; Mawhinney, J.; Weis, D. Bupropion for the treatment of methamphetamine dependence. Neuropsychopharmacology 2008, 33, 1162-1170.
33. Shoptaw, S.; Heinzerling, K. G.; Rotheram-Fuller, E.; Steward, T.; Wang, J.; N., S. A.; De La Garza, R.; Newton, T.; Ling, W. Randomized, placebo-controlled trial of bupropion for the treatment of methamphetamine dependence. Drug Alcohol Depend. 2008, 96, 222-232.
34. Zugibe, F. T.; Breithaupt, M.; Costello, J. Cardiotoxic mechanisms and interrelationships of cocaine: including a single case depicting several of these mechanisms. J. Clin. Forensic Med. 1998, 5, 140-146.
35. Volkow, N. D. Stimulant medications: how to minimize their reinforcing effects? Am. J. Psychiatry 2006, 163, 359-361. (Pubitemid 44469374)
36. Volkow, N. D.; Ding, Y. S.; Fowler, J. S.; Wang, G. J.; Logan, J.; Gatley, J. S.; Dewey, S.; Ashby, C.; Liebermann, J.; Hitzemann, R.; et al. Is methylphenidate like cocaine? Studies on their pharmacokinetics and distribution in the human brain. Arch. Gen. Psychiatry 1995, 52, 456-463.
37. Quinn, D. I.; Wodak, A.; Day, R. O. Pharmacokinetic and pharmacodynamic principles of illicit drug use and treatment of illicit drug users. Clin. Pharmacokinet. 1997, 33, 344-400.
38. Gorelick, D. A. The rate hypothesis and agonist substitution approaches to cocaine abuse treatment. Adv. Pharmacol. 1998, 42 (Catecholamines), 995-997.
39. Mehta, N. B. The chemistry of bupropion. J. Clin. Psychiat. 1983, 45, 56-59.
40. Chenard, B. L.; Bordner, J.; Butler, T. W.; Chambers, L. K.; Collins, M. A.; De Costa, D. L.; Ducat, M. F.; Dumont, M. L.; Fox, C. B.; Mena, E. E.; Menniti, F. S.; Nielsen, J.; Pagnozzi, M. J.; Richter, K. E. G.; Ronau, R. T.; Shalaby, I. A.; Stemple, J. Z.; White, W. F. (1S,2S)-1-(4-Hydroxyphenyl)-2-(4- hydroxy-4-phenylpiperidino)-1-propanol: A potent new neuroprotectant which blocks N-methyl-D-aspartate responses. J. Med. Chem. 1995, 38, 3138-3145.
41. 10 monocyclic aromatic hydrocarbons. J. Am. Chem. Soc. 1949, 71, 1362-1369.
42. Bailey, W. F.; Punzalan, E. R. Convenient general method for the preparation of primary alkyllithiums by lithium-iodine exchange. J. Org. Chem. 1990, 55, 5404-5406.
43. Musso, D. L.; Mehta, N. B.; Soroko, F. E. Synthesis and evaluation of the anticonvulsant activity of a series of 2-amino-1-phenyl-1-propanols derived from the metabolites of the antidepressant bupropion. Bioorg. Med. Chem. Lett. 1997, 7, 1-6.
44. Foley, K. F.; Cozzi, N. V. Novel aminopropiophenones as potential antidepressants. Drug Develop. Res. 2003, 60, 252-260.
45. Eshleman, A. J.; Carmolli, M.; Cumbay, M.; Martens, C. R.; Neve, K. A.; Janowsky, A. Characteristics of drug interactions with recombinant biogenic amine transporters expressed in the same cell type. J. Pharmacol. Exp. Ther. 1999, 289, 877-885.
46. Froimowitz, M.; Wu, K. M.; Moussa, A.; Haidar, R. M.; Jurayj, J.; George, C.; Gardner, E. L. Slow-onset, long-duration 3-(3′,4′- dichlorophenyl)-1-indanamine monoamine reuptake blockers as potential medications to treat cocaine abuse. J. Med. Chem. 2000, 43, 4981-4992.
47. Katz, J. L.; Agoston, G. E.; Alling, K. L.; Kline, R. H.; Forster, M. J.; Woolverton, W. L.; Kopajtic, T. A.; Newman, A. H. Dopamine transporter binding without cocaine-like behavioral effects: synthesis and evaluation of benztropine analogs alone and in combination with cocaine in rodents. Psychopharmacology (Berl.) 2001, 154, 362-374.
48. Gonzalez, L. A.; Gatch, M. B.; Taylor, C. M.; Bell-Horner, C. L.; Forster, M. J.; Dillon, G. H. Carisoprodol-mediated modulation of GABAA receptors: in vitro and in vivo studies. J. Pharmacol. Exp. Ther. 2009, 329, 827-837.
49. Carroll, F. I.; Fox, B. S.; Kuhar, M. J.; Howard, J. L.; Pollard, G. T.; Schenk, S. Effects of dopamine transporter selective 3-phenyltropane analogs on locomotor activity, drug discrimination, and cocaine self-administration after oral administration. Eur. J. Pharmacol. 2006, 553, 149-156.
50. Gatch, M. B.; Taylor, C. M.; Flores, E.; Selvig, M.; Forster, M. J. Effects of monoamine oxidase inhibitors on cocaine discrimination in rats. Behav. Pharmacol. 2006, 17, 151-159.
51. Rau, K. S.; Birdsall, E.; Hanson, J. E.; Johnson-Davis, K. L.; Carroll, F. I.; Wilkins, D. G.; Gibb, J. W.; Hanson, G. R.; Fleckenstein, A. E. Bupropion increases striatal vesicular monoamine transport. Neuropharmacology 2005, 49, 820-830.
52. Meyer, J. H.; Goulding, V. S.; Wilson, A. A.; Hussey, D.; Christensen, B. K.; Houle, S. Bupropion occupancy of the dopamine transporter is low during clinical treatment. Psychopharmacology (Berl.) 2002, 163, 102-105. (Pubitemid 34985318)
53. Learned-Coughlin, S. M.; Bergstrom, M.; Savitcheva, I.; Ascher, J.; Schmith, V. D.; Langstrom, B. In vivo activity of bupropion at the human dopamine transporter as measured by positron emission tomography. Biol. Psychiatry 2003, 54, 800-805.
54. 99mTc-TRODAT-1 SPECT study. J. Affect. Disord. 2005, 89, 115-123.
55. Dackis, C. A.; Gold, M. S. New concepts in cocaine addiction: The dopamine depletion hypothesis. Neurosci. Biobehav. Rev. 1985, 9, 469-477.
56. Volkow, N. D.; Wang, G. J.; Fowler, J. S.; Logan, J.; Gatley, S. J.; Hitzemann, R.; Chen, A. D.; Dewey, S. L.; Pappas, N. Decreased striatal dopaminergic responsiveness in detoxified cocaine-dependent subjects. Nature 1997, 386, 830-833. (Pubitemid 27181256)
57. Meltzer, P. C.; Butler, D.; Deschamps, J. R.; Madras, B. K. 1-(4- Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors. J. Med. Chem. 2006, 49, 1420-1432.
58. Broadbent, J.; Michael, E. K.; Riddle, E. E.; Apple, J. B. Involvement of dopamine uptake in the discriminative stimulus effects of cocaine. Behav. Pharmacol. 1991, 2, 187-197.
59. Broadbent, J.; Gaspard, T. M.; Dworkin, S. I. Assessment of the discriminative stimulus effects of cocaine in the rat: lack of interaction with opioids. Pharmacol., Biochem. Behav. 1995, 51, 379-385.
60. Howell, L. L.; Carroll, F. I.; Votaw, J. R.; Goodman, M. M.; Kimmel, H. L. Effects of combined dopamine and serotonin transporter inhibitors on cocaine self-administration in rhesus monkeys. J. Pharmacol. Exp. Ther. 2007, 320, 757-765.
61. de Fiebre, C. M.; de Fiebre, N. E.; Coleman, S. L.; Forster, M. J. Comparison of the actions of gamma-butyrolactone and 1,4- butanediol in Swiss-Webster mice. Pharmacol., Biochem. Behav. 2004, 77, 705-710.