Synthesis of 1,1-[1-Naphthyloxy-2-thiophenyl]-2-methylaminomethylcyclopropanes and Their Evaluation as Inhibitors of Serotonin, Norepinephrine, and Dopamine Transporters

Journal of Medicinal Chemistry
2009.0

Abstract

Stereodefined trisubstituted cyclopropanes bearing naphthyloxy, thiophenyl, and (N-methylamino)methyl groups were synthesized in enantiopure form employing asymmetric cyclopropanation of (E)- and (Z)-allylic alcohols as the key step. In vitro assays of the synthesized cyclopropanes revealed that the K(i) of one of the enantiomers as a dual inhibitor of serotonin and norepinephrine transporters is in the low nanomolar range and is comparable to that of duloxetine.

Knowledge Graph

Similar Paper

Synthesis of 1,1-[1-Naphthyloxy-2-thiophenyl]-2-methylaminomethylcyclopropanes and Their Evaluation as Inhibitors of Serotonin, Norepinephrine, and Dopamine Transporters
Journal of Medicinal Chemistry 2009.0
Synthesis, inhibition and binding of simple non-nitrogen inhibitors of monoamine transporters
Bioorganic & Medicinal Chemistry 2007.0
Synthesis and Monoamine Transporter Binding Properties of 2,3-Cyclo Analogues of 3β-(4‘-Aminophenyl)-2β-tropanemethanol
Journal of Medicinal Chemistry 2006.0
Discovery of N-methyl-1-(1-phenylcyclohexyl)methanamine, a novel triple serotonin, norepinephrine, and dopamine reuptake inhibitor
Bioorganic & Medicinal Chemistry Letters 2011.0
Synthesis and pharmacological evaluation of ( Z )-9-(Heteroarylmethylene)-7-azatricyclo[4.3.1.0 3,7 ]decanes: thiophene analogues as potent norepinephrine transporter inhibitors
Bioorganic & Medicinal Chemistry Letters 2003.0
Novel Conformationally Constrained Tropane Analogues by 6-endo-trig Radical Cyclization and Stille Coupling − Switch of Activity toward the Serotonin and/or Norepinephrine Transporter
Journal of Medicinal Chemistry 2000.0
Bicyclo[3.2.1]octanes: Synthesis and inhibition of binding at the dopamine and serotonin transporters
Bioorganic & Medicinal Chemistry Letters 1999.0
Discovery of N-methyl-1-(1-phenylcyclohexyl)ethanamine, a novel triple serotonin, norepinephrine and dopamine reuptake inhibitor
Bioorganic & Medicinal Chemistry Letters 2011.0
3-(Arylamino)-3-phenylpropan-2-olamines as a new series of dual norepinephrine and serotonin reuptake inhibitors
Bioorganic & Medicinal Chemistry Letters 2009.0
Synthesis of 8-thiabicyclo[3.2.1]oct-2-enes and their binding affinity for the dopamine and serotonin transporters
Bioorganic & Medicinal Chemistry Letters 2004.0