Further structure-activity relationship studies of piperidine-based monoamine transporter inhibitors: Effects of piperidine ring stereochemistry on potency. Identification of norepinephrine transporter selective ligands and broad-spectrum transporter inhibitors

Journal of Medicinal Chemistry

Volumn 48, Issue 25, 2005, Pages 7970-7979

  He, Rong ^a   Kurome, Toru ^a   Giberson, Kelly M ^b   Johnson, Kenneth M ^b   Kozikowski, Alan P ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

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

Author keywords

[No Author keywords available]

Indexed keywords

4 (4 CHLOROPHENYL)PIPERIDINE DERIVATIVE; DOPAMINE TRANSPORTER; MODAFINIL; NORADRENALIN TRANSPORTER; PIPERIDINE DERIVATIVE; SEROTONIN TRANSPORTER; THIOACETAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DEPRESSION; DRUG EFFICACY; DRUG INHIBITION; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANIMALS; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; LIGANDS; NERVE ENDINGS; NOREPINEPHRINE PLASMA MEMBRANE TRANSPORT PROTEINS; PIPERIDINES; RADIOLIGAND ASSAY; RATS; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; SEROTONIN UPTAKE INHIBITORS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFIDES; SYNAPTOSOMES;

EID: 29144464771     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050694s     Document Type: Article

References (31)

1. Greengard, P. The neurobiology of slow synaptic transmission. Science 2001, 294, 1024-1030.
2. 125I]-2β-carbomethoxy-3β- (4-iodophenyl) tropane and single photon emission computed tomography. Biol. Psychiatry 1998, 44, 1090-1098.
3. (b) Kim, H. J. Imaging and quantitation of dopamine transporters with iodine-123-IPT in normal and Parkinson's disease subjects. J. Nucl. Med. 1997, 38, 1703-1711.
4. (c) Dougherty, D. D. Dopamine transporter density in patients with attention deficit hyperactivity disorder. Lancet 1999, 354, 2132-2133.
5. (a) Rowley, M.; Bristow, L. J.; Hutson, P. H. Current and novel approaches to the drug treatment of schizophrenia. J. Med. Chem. 2001, 44, 477-501.
6. (b) Amara, S. G.; Sonders, M. S. Neurotransmitter transporters as molecular targets for addictive drugs. Drug Alcohol Depend. 1998, 51, 87-96.
7. (c) Terres, G. E.; Gainetdinov, R. R.; Caron, M. G. Plasma membrane monoamine transporters: Structure, regulation and function. Nat. Rev. Neurosci. 2003, 4, 13-25.
8. (a) 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.
9. (b) Kuhar, M. J. Molecular pharmacology of cocaine: a dopamine hypothesis and its implications. Ciba Found. Symp. 1992, 766, 81-89.
10. (c) Wise, R. A. Neurobiology of addiction. Curr. Opin. Neurobiol. 1996, 6, 243-251.
11. (d) Carroll, F. I. Monoamine transporters and opioid receptors. Targets for addiction therapy. J. Med. Chem. 2003, 46, 1775-1794.
12. (a) Wong, D. T.; Bymaster, F. P.; Engleman, E. A. Prozac (Fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: Twenty years since the first publication. Life Sci. 1995, 57, 411-441.
13. (b) Dechant, K. L.; Clissold, S. P. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potentials in depressive illness. Drugs 1991, 52, 625-638.
14. Zhou, J. Norepinephrine transporter inhibitors and their therapeutic potential. Drugs Future 2004, 29, 1235-1244.
15. Bryan-Lluka, L. J.; Bönisch, H.; Lewis, R. J. χConopeptide MrIA partially overlaps desipramine and cocaine binding sites on the human norepinephrine transporter. J. Biol. Chem. 2003, 278, 40324-40329.
16. Cao, J.; Lever, J. R.; Kopajtic, T.; Katz, J. L.; Pham, A. T.; Holmes, M. L.; Justice, J. B.; Newman, A. H. Novel azido and isothiocyanato analogues of [3-(4-phenylalkylpiperazin-1-yl)-propyl] bis(4-fluorophenyl)amines as potential irreversible ligands for the dopamine transporter. J. Med. Chem. 2004, 47, 6128-6136.
17. (a) Zhou, J.; Zhang, A.; Klass, T.; Johnson, K. M.; Wang, C. Z.; Ye, Y.; Kozikowski, A. P. Biaryl analogues of conformationally constrained tricyclic tropanes as potent and selective norepinephrine reuptake inhibitors: synthesis and evaluation of their uptake inhibition at monoamine transporter sites. J. Med. Chem. 2003, 46, 1997-2007.
18. (b) Zhou, J.; Kläss, T.; Zhang, A.; Johnson, K. M.; Wang, C. Z.; Ye, Y.; Kozikowski, A. P. Synthesis and pharmacological evaluation of (Z)-9-(heteroarylmethylene)-7-azatricyclo[4.3.1.0(3,7)]decanes: thiophene analogues as potent norepinephrine transporter inhibitors. Bioorg. Med. Chem. Lett. 2003, 13, 3565-3569.
19. (a) Kozikowski, A. P.; Araldi, G. L.; Boja, J.; Meil, W. M.; Johnson, K. M.; Flippen-Aderson, J. L.; George, C.; Saiah, E. Chemistry and pharmacology of the piperidine-based analogues of cocaine. Identification of potent DAT inhibitors lacking the toropane skeleton. J. Med. Chem. 1998, 41, 1, 1962-1969.
20. (b) Tamiz, A. P.; Zhang, J.; Flippen-Anderson, J. L.; Zhang, M.; Johnson, K. M.; Deschaux, O.; Tella, S. R.; Kozikowski, A. P. Further SAR studies of piperidine-based analogues of cocaine. 2. Potent dopamine and serotonine reuptake inhibitors. J. Med. Chem. 2000, 43, 1215-1222.
21. (c) Kozikowski, A. P.; Johnson, K. M.; Deschaux, O.; Bandyopadhyay, B. C.; Araldi, G. L.; Carmona, G.; Munzar, P.; Simth, M. P.; Balster, R. L.; Beardsley, P. M.; Tella, S. R. Mixed cocaine agonist/antagonist properties of (+)-methyl 4-(4-chlorophenyl)-l-methylpiperidine-3-carboxylate, a piperidine-based analog of cocaine. J. Pharmacol. Exp. Ther. 2003, 305, 143-150.
22. (d) Petukhov, P. A.; Zhang, M.; Johnson, K. M.; Tella, S. R.; Kozikowski, A. P. SAR studies of piperidine-based analogues of cocaine. Part 3: Oxadiazoles. Bioorg. Med. Chem. Lett. 2001, 11, 2079-2083.
23. (a) Mignot, E.; Nishino, S.; Guilleminault, C.; Dement, W. C. Modafinil binds to the dopamine uptake carrier site with low affinity. Sleep 1994, 17, 436-437.
24. (b) Nishino, S.; Mao, J.; Sampathkumaran, R.; Shelton, J.; Mignot, E. Increased dopaminergic transmittion mediates the wake-promoting effects of CNS stimulants. Sleep Res. Online 1998, 1, 49-61.
25. Zhou, J.; He, R.; Johnson, K. M.; Ye, Y.; Kozikowski, A. P. Piperidine-based nocaine/modafinil hybrid ligands as highly potent monoamine transporter inhibitors: Efficient drug discovery by rational lead hybridization. J. Med. Chem. 2004, 47, 5821-5824.
26. Yuan, H.; Kozikowski, A. P.; Petukhov, P. A. CoMFA study of piperidine analogues of cocaine at the dopamine transporter: Exploring the binding mode of the 3-substitution of the piperidine ring using pharmacophore-based flexible alignment. J. Med. Chem. 2004, 47, 6137-6143.
27. Garcia-Alloza, M.; Bacskai, B. J. Techniques for brain imaging in vivo. Neuromol. Med. 2004, 6, 65-78.
28. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 1997, 23, 3-25.
29. Petukhov, P. A.; Zhang, J.; Wang, C. Z.; Ye, Y.; Johnson, K. M.; Kozikowski, A. P. Synthesis, molecular modeling, and biological studies of novel piperidine-based analogues of cocaine: Evidence of unfavorable interactions proximal to the 3-position of the piperidine ring. J. Med. Chem. 2004, 47, 3009-3018.
30. Hajös, M.; Fleishaker, J. C.; Filipiak-Reisner, J. K.; Brown, M. T.; Wong, E. H. The selective norepinephrine reuptake inhibitor antidepressant reboxetine: pharmacological and clinical profile. CNS Drug Rev. 2004, 10, 23-44.
31. Skolnick, P.; Popik, P.; Janowsky, A.; Beer, B.; Lippa, A. S. "Broad spectrum" antidepressants: Is more better for the treatment of depression? Life Sci. 2003, 73, 3175-3179.