The synthesis and biological evaluation of dopamine transporter inhibiting activity of substituted diphenylmethoxypiperidines

Bioorganic & Medicinal Chemistry Letters
2005.0

Abstract

The synthesis of potent 4-aryl methoxypiperidinol inhibitors of the dopamine transporter is described. Symmetrical para substituents of the benzene rings are important for high potency in binding to the dopamine transporter. 4-[Bis(4-fluorophenyl) methoxy]-1-methylpiperidine has an IC50 of 22.1+/-5.73 nM and increases locomotor activity in mice.

Knowledge Graph

Similar Paper

The synthesis and biological evaluation of dopamine transporter inhibiting activity of substituted diphenylmethoxypiperidines
Bioorganic & Medicinal Chemistry Letters 2005.0
Pharmacophore-Based discovery, synthesis, and biological evaluation of 4-phenyl-1-arylalkyl piperidines as dopamine transporter inhibitors
Bioorganic & Medicinal Chemistry Letters 2001.0
Identification of a novel partial inhibitor of dopamine transporter among 4-substituted 2-phenylquinazolines
Bioorganic & Medicinal Chemistry Letters 2002.0
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
Further SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors
Journal of Medicinal Chemistry 2000.0
Novel 4'-Substituted and 4',4''-Disubstituted 3.alpha.-(Diphenylmethoxy)tropane Analogs as Potent and Selective Dopamine Uptake Inhibitors
Journal of Medicinal Chemistry 1995.0
Synthesis and Pharmacology of Potential Cocaine Antagonists. 2. Structure−Activity Relationship Studies of Aromatic Ring-Substituted Methylphenidate Analogs
Journal of Medicinal Chemistry 1996.0
3‘-Chloro-3α-(diphenylmethoxy)tropane But Not 4‘-Chloro-3α- (diphenylmethoxy)tropane Produces a Cocaine-like Behavioral Profile
Journal of Medicinal Chemistry 1997.0
Structure-activity relationships for a series of (Bis(4-fluorophenyl)methyl)sulfinylethyl-aminopiperidines and -piperidine amines at the dopamine transporter: Bioisosteric replacement of the piperazine improves metabolic stability
European Journal of Medicinal Chemistry 2020.0
Synthesis and Ligand Binding Studies of 4‘-Iodobenzoyl Esters of Tropanes and Piperidines at the Dopamine Transporter
Journal of Medicinal Chemistry 1997.0