Abstract
The synthesis and biological evaluation of 3,4,5-trimethoxyphenyl acrylamides 1a-f as novel antinarcotic agents are described. The molecules were prepared by the Wittig reaction, followed by a coupling reaction between 3,4,5-trimethoxycinnamic acid (9) and aliphatic amines, which resulted in good yields. When tested for biological activity, compounds 1d-f exhibited strong inhibitory effects on the morphine withdrawal syndrome in mice due to their high binding affinities with serotonergic 5-HT1A receptors.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acrylamides / chemical synthesis*
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Acrylamides / chemistry
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Acrylamides / metabolism
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Acrylamides / pharmacology*
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Animals
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Cells, Cultured
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Drug Design
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Drug Evaluation, Preclinical
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Magnetic Resonance Spectroscopy
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Mice
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Mice, Inbred C57BL
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Narcotic Antagonists / chemical synthesis*
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Narcotic Antagonists / chemistry
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Narcotic Antagonists / metabolism
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Narcotic Antagonists / pharmacology*
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Radioligand Assay
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Receptor, Serotonin, 5-HT1A / drug effects
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Spectrometry, Mass, Electrospray Ionization
Substances
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Acrylamides
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Narcotic Antagonists
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Receptor, Serotonin, 5-HT1A