Synthesis and evaluation of novel-N-[2-(bis-aryl-methoxy)ethyl-N′-aralkyl-α,ω-alkanediamines as potent and selective dopamine reuptake inhibitors: Seco analogs of GBR12935 and GBR12909

Bioorganic & Medicinal Chemistry Letters
1997.0

Abstract

A series of analogs of the N-[2-bis arylmethoxy]-N'-phenylpropyl-piperazines GBR12909 and 12935 was synthesized and evaluated as inhibitors of synaptic monoamine transporters. The data indicated that all of the new compounds demonstrated a selectivity for the dopamine transporter compared to the other monoamine transporters with IC50 values approaching 10 nM. The results suggest that the internal piperazine moiety is not required for activity and may be replaced with a more flexible diamine unit.

Knowledge Graph

Similar Paper

Synthesis and evaluation of novel-N-[2-(bis-aryl-methoxy)ethyl-N′-aralkyl-α,ω-alkanediamines as potent and selective dopamine reuptake inhibitors: Seco analogs of GBR12935 and GBR12909
Bioorganic & Medicinal Chemistry Letters 1997.0
Design, Synthesis, and Biological Evaluation of Novel Non-Piperazine Analogues of 1-[2-(Diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines as Dopamine Transporter Inhibitors
Journal of Medicinal Chemistry 1999.0
Development of Novel, Potent, and Selective Dopamine Reuptake Inhibitors through Alteration of the Piperazine Ring of 1-[2-(Diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909)
Journal of Medicinal Chemistry 1996.0
Novel 3-Aminomethyl- and 4-Aminopiperidine Analogues of 1-[2-(Diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazines:  Synthesis and Evaluation as Dopamine Transporter Ligands
Journal of Medicinal Chemistry 2000.0
Synthesis and biological evaluation of novel 3,4-diaryl lactam derivatives as triple reuptake inhibitors
Bioorganic & Medicinal Chemistry Letters 2013.0
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 2002.0
Design and Synthesis of 2- and 3-Substituted-3-phenylpropyl Analogs of 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(Diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine: Role of Amino, Fluoro, Hydroxyl, Methoxyl, Methyl, Methylene, and Oxo Substituents on Affinity for the Dopamine and Serotonin Transporters
Journal of Medicinal Chemistry 2008.0
Synthesis and dopamine transporter binding affinities of 3α-Benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes
Bioorganic & Medicinal Chemistry Letters 2002.0
[3-cis-3,5-Dimethyl-(1-piperazinyl)alkyl]-bis-(4′-fluorophenyl)amine analogues as novel probes for the dopamine transporter
Bioorganic & Medicinal Chemistry Letters 2001.0
Further SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors
Journal of Medicinal Chemistry 2000.0