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• W2022222791 abstract "We recently demonstrated that (±)-(Z)-2-(aminomethyl)-1-phenyl-N,N-diethylcyclopropanecarboxamide [milnacipran, (±)-1], an inhibitor of the reuptake of serotonin (5-HT), was a noncompetitive NMDA receptor antagonist. On the basis of the cyclopropane structure of (±)-1, conformationally restricted analogs with different stereochemistries, namely 1-phenyl-2-(1-aminoalkyl)-N,N-diethylcyclopropanecarboxamindes (2, 3, ent-2, and ent-3), were designed and synthesized. Among these analogs, 2a, 2b, and 2f, with (1S,2R,1‘S)-configuration, were more efficient than milnacipran as NMDA receptor antagonists; these compounds significantly inhibited the binding of [3H]MK-801 at IC50 = 0.35 ± 0.08, 0.20 ± 0.024, and 0.16 ± 0.02 μM, respectively, and blocked the response of voltage-clamped oocytes to NMDA, surpassing the effects of (±)-1. Although both the 1‘-methyl analog 2a and the 1‘-vinyl analog 2f, like (±)-1, strongly inhibited 5-HT uptake in vitro, the corresponding 1‘-ethyl analog 2b was devoid of the inhibitory effect on 5-HT uptake, while it was about 30 times more potent as an NMDA receptor antagonist than (±)-1." @default.
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• W2022222791 date "1996-01-01" @default.
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• W2022222791 title "Synthesis and Biological Activity of Conformationally Restricted Analogs of Milnacipran: (1<i>S</i>,2<i>R</i>)-1-Phenyl-2-[(<i>S</i>)-1-aminopropyl]-<i>N</i>,<i>N</i>-diethylcyclopropanecarboxamide, an Efficient Noncompetitive <i>N</i>-Methyl-<scp>d</scp>-aspartic Acid Receptor Antagonist" @default.
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• W2022222791 doi "https://doi.org/10.1021/jm960495w" @default.
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