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.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Animals
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Cyclopropanes / chemical synthesis*
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Cyclopropanes / pharmacology*
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Dopamine Plasma Membrane Transport Proteins / antagonists & inhibitors
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Duloxetine Hydrochloride
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Humans
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Norepinephrine Plasma Membrane Transport Proteins / antagonists & inhibitors
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Plasma Membrane Neurotransmitter Transport Proteins / antagonists & inhibitors*
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Serotonin Antagonists
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Serotonin Plasma Membrane Transport Proteins / drug effects
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Stereoisomerism
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Structure-Activity Relationship
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Thiophenes
Substances
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Cyclopropanes
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Dopamine Plasma Membrane Transport Proteins
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Norepinephrine Plasma Membrane Transport Proteins
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Plasma Membrane Neurotransmitter Transport Proteins
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Serotonin Antagonists
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Serotonin Plasma Membrane Transport Proteins
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Thiophenes
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Duloxetine Hydrochloride