Expansion of structure-activity studies of piperidine analogues of 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine (GBR 12935) compounds by altering substitutions in the N-benzyl moiety and behavioral pharmacology of selected molecules

Journal of Medicinal Chemistry

Volumn 45, Issue 3, 2002, Pages 654-662

  Dutta, Aloke K ^a   Davis, Matthew C ^a,b   Fei, Xiang Shu ^a   Beardsley, Patrick M ^c   Cook, Charles D ^c   Reith, Maarten E A ^d  

^a WAYNE STATE UNIVERSITY   (United States)

^b NAVAL AIR WARFARE CENTER   (United States)

^c VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^d UNIVERSITY OF ILLINOIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 (BENZHYDRYLOXY)ETHYL] 4 (3 PHENYLPROPYL)PIPERAZINE; PIPERIDINE DERIVATIVE;

AMINO ACID SUBSTITUTION; ARTICLE; BEHAVIOR; BINDING AFFINITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG UPTAKE; NEUROTRANSMITTER RELEASE; SEROTONIN RELEASE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; BINDING, COMPETITIVE; BRAIN; CARRIER PROTEINS; COCAINE; DISCRIMINATION LEARNING; DOPAMINE; DOPAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; LIGANDS; MALE; MEMBRANE GLYCOPROTEINS; MEMBRANE TRANSPORT PROTEINS; MICE; MOTOR ACTIVITY; NERVE TISSUE PROTEINS; NOREPINEPHRINE; NOREPINEPHRINE PLASMA MEMBRANE TRANSPORT PROTEINS; PIPERAZINES; PIPERIDINES; RADIOLIGAND ASSAY; RATS; SEROTONIN; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; SYMPORTERS;

EID: 0037204043     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010316x     Document Type: Article

References (49)

1. Overview of potential treatment medications for cocaine dependence
2. Pharmacotherapies for Treatment of Cocaine Abuse: Preclinical Aspects
3. Cocaine inhibition of ligand binding at dopamine, norpinephrine and serotonin transporters: A structure-activity study
4. Cocaine receptors on dopamine transporters are related to self-adminstration of cocaine
5. Effects of cocaine and related drugs in nonhuman primates. II. Stimulant effects on schedule-controlled behavior
6. The dopamine hypothesis of the reinforcing properties of cocaine
7. Cellular and molecular mechanisms of drug dependence
8. Behavioral effects of selective dopaminergic compounds in rats discriminating cocaine injections
9. Hyperlocomotion and indifference to cocaine and amphetamine in mice lacking the dopamine transporter
10. Drugs abused by humans preferentially increase synaptic dopamine concentrations in the mesolimbic system of freely moving rats
11. Cocaine and amphetamine increase extracellular dopamine in the nucleus accumbens of mice lacking the dopamine transporter gene
12. Cocaine self-administration in dopamine transporter knockout mice
13. Regulation of extracellular dopamine by the norepinephrine transporter
14. Characteristics of drug interactions with recombinant biogenic amine transporters expressed in the same cell type
15. Dopaminergic agents for the treatment of cocaine abuse
16. Dopamine transporter uptake blockers: Structure activity relationships
17. Chemistry, design, and structure-activity relationship of cocaine antagonists
18. structure-activity relationship studies of novel 4-[2-[bis(4-fluorophenyl)methoxy]ethyl]-1-(3-phenylpropyl)piperidine analogues: Synthesis and biological evaluation at the dopamine and serotonin transporter sites
19. Highly selective, novel analogues of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine for the dopamine transporter: Effect of different aromatic substitutions on their affinity and selectivity
20. Potent and selective ligands for the dopamine transporter (DAT): Structure-activity relationship studies of novel 4-[2-(diphenylmethoxy)ethyl]-1-(3-phenylpropyl)piperidine analogues
21. Tolerance in the replacement of the benzhydrylic O-atom in 4-[2-(Diphenyl-methoxy)-ethyl]-1-benzylpiperidine derivatives by an N-atom: Development of new-generation potent and selective N-analogue molecules for the dopamine transporter
22. Structure-activity relationship studies of 4-[2-(diphenylmethoxy)-ethyl]-l-benzylpiperidine derivatives and their nanalogues: Evaluation of behavioral activity of O- and N-analogues and their binding to monoamine transporters
23. 3h] GBR 12935 binding in vitro to rat striatal membranes: Labeling of thedopamine uptake complex
24. Aryl 1,4-dialk(en)ylpiperazines as selective and very potent inhibitors of dopamine uptake
25. Design, synthesis, and characterization of a novel, 4-[2-(diphenylmethoxy)ethyl]-1-benzyl piperidine-based, dopamine transporter photoaffinity label
26. Dual incorporation of photoaffinity ligands on dopamine transporters implicates proximity of labeled domains
27. Dopamine transporter ligand binding domains: Structural and functional properties revealed by limited proteolysis
28. Differential binding of tropane-based photoaffinity ligands on the dopamine transporter
29. Complex interaction of cocaine with the dopamine uptake carrier
30. Cocaine and GBR 12783 recognize nonidentical, overlapping binding domains on the dopamine neuronal carrier
31. Cocaine and GBR 12909 produce equivalent motoric reponses at different occupancy of the dopamine transporter
32. Differential reinforcing effects of cocaine and GBR 12909: Biochemical evidence for divergent neuroadaptive changes in the mesolimbic dopaminergic system
33. Differential relationships among dopamine transporter affinities and stimulant potencies of various uptake inhibitors
34. Novel 3adiphenylmethoxytropane analogues: Selective dopamine uptake inhibitors with behavioral effects distinct from those of cocaine
35. Dopamine transporter site-directed mutations differentially alter substrate transport and cocaine binding
36. Delineation of discrete domains for substrate, cocaine and tricyclic antidepressant interactions using chimeric dopaminenorepinephrine transporters
37. Effects of the longacting monoamine reuptake inhibitor indatraline on cocaine selfadministration in rhesus monkeys
38. The rate hypothesis and agonist substitution approaches to cocaine abuse treatment
39. Review of the effects of dopaminergic agents on humans, animals, and drug-seeking behavior, and its implications for medication development. Focus on GBR 12909
40. Sustained decrease in cocaine-maintained responding in rhesus monkeys with 1-[2-[bis(4-fluorophenyl)-methoxy] ethyl]4-(3-hydroxy-3-phenylpropyl)piperazinyl decanoate, a long-acting ester derivative of GBR 12909
41. Synthesis and transporter binding properties of 3β-(4′-Alkyl-, 4′-alkenyl-, and 4′-alkynylphenyl)nortropane2β-carboxylic acid methyl esters: Serotonin transporter selective analogues
42. Synthesis of functional styrenes via palladium-catalyzed coupling of aryl bromides with vinyl tin reagents
43. 3-receptor antagonists with high oral central nervous system activity
44. Novel N-substituted 3α-[bis(4′fluorophenyl)methoxy]tropane analogues: Selective ligands for the dopamine transporter
45. Pharmacological characterization of the discriminative-stimulus effects of GBR 12909
46. Translocation of dopamine and binding of 2β-carbomethoxy-3β-(4-fluorophenyl)tropane (WIN 35, 428) measured under identical conditions in rat striatal synaptosomal preparations. Inhibition by various blockers