Abstract
Herein, we report the rational design and synthesis of novel 2,5-disubstituted piperidine derivatives in the cis and trans isomeric forms. Out of these two isomers, the cis-isomer, 7a, was found to exhibit the most potent activity and selectivity for the dopamine transporter. These novel derivatives represent conformationally constrained version of piperidine analogue of GBR compounds.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Benzhydryl Compounds / chemistry*
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Benzhydryl Compounds / pharmacology*
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Brain / drug effects
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Brain / metabolism
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Carrier Proteins / drug effects
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Carrier Proteins / metabolism
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Citalopram / metabolism
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Cocaine / analogs & derivatives*
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Cocaine / metabolism
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Dopamine Plasma Membrane Transport Proteins
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Dopamine Uptake Inhibitors / metabolism
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Drug Design
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Drug Evaluation, Preclinical
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Isomerism
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Magnetic Resonance Spectroscopy
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Membrane Glycoproteins / drug effects
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Membrane Glycoproteins / metabolism
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Membrane Transport Proteins / drug effects*
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Membrane Transport Proteins / metabolism
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Nerve Tissue Proteins*
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Piperidines / chemistry*
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Piperidines / pharmacology*
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Selective Serotonin Reuptake Inhibitors / metabolism
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Serotonin Plasma Membrane Transport Proteins
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Structure-Activity Relationship
Substances
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5-(4-fluorophenylmethylamino)-2-(diphenylmethyl)piperidine
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Benzhydryl Compounds
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Carrier Proteins
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Dopamine Plasma Membrane Transport Proteins
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Dopamine Uptake Inhibitors
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Membrane Glycoproteins
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Membrane Transport Proteins
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Nerve Tissue Proteins
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Piperidines
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Serotonin Plasma Membrane Transport Proteins
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Serotonin Uptake Inhibitors
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Citalopram
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(1R-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester
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Cocaine