Abstract
A series of N-aromatic, N-heteroaromatic, and oxygenated N-phenylpropyl derivatives of 1-(2-benzhydryloxyethyl)-piperazine and 1-[2-[bis-(4-fluorophenyl)methoxy]ethyl]piperazine, analogues of GBR 12909 (1a) and 12935 (1b), was synthesized and examined for their dopamine (DAT) and serotonin (SERT) transporter binding properties. One of these compounds, racemic 3-[4-(2-benzhydryloxyethyl)piperazin-1-yl]-1-(3-fluorophenyl)-propan-1-ol (33), had DAT affinity as good as, or better than, GBR 12909 and 12935, and was more selective for DAT over SERT than the GBR compounds. Both trans- (43) and cis- (47) (+/-)-2-(4-[2-[bis-(4-fluorophenyl)-methoxy]ethyl]piperazin-1-ylmethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol had relatively good SERT selectivity and, as well, showed high affinity for SERT.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alcohols
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Carrier Proteins / chemistry*
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Carrier Proteins / drug effects
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Dopamine Plasma Membrane Transport Proteins
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Heterocyclic Compounds / chemical synthesis
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Heterocyclic Compounds / chemistry
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Heterocyclic Compounds / pharmacology
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Kinetics
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Mannich Bases
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Membrane Glycoproteins / chemistry*
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Membrane Glycoproteins / drug effects
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Membrane Transport Proteins / chemistry*
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Membrane Transport Proteins / drug effects
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Nerve Tissue Proteins*
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Piperazines / chemistry
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Piperazines / pharmacology*
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Protein Binding
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Serotonin Plasma Membrane Transport Proteins
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Structure-Activity Relationship
Substances
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Alcohols
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Carrier Proteins
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Dopamine Plasma Membrane Transport Proteins
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Heterocyclic Compounds
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Mannich Bases
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Membrane Glycoproteins
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Membrane Transport Proteins
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Nerve Tissue Proteins
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Piperazines
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Serotonin Plasma Membrane Transport Proteins
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vanoxerine
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1-(2 (diphenylmethoxy)ethyl)-4-(3-phenylpropyl)piperazine