Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT(2)-selective melatonin ligands

A series of substituted N-[3-(3-methoxyphenyl)propyl] amides were synthesized and their binding affinities towards human melatonin MT(1) and MT(2) receptors were evaluated. It was discovered that a benzyloxyl substituent incorporated at C6 position of the 3-methoxyphenyl ring dramatically enhanced t...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2010-04, Vol.20 (8), p.2582-2585
Main Authors: Hu, Yueqing, Ho, Maurice K C, Chan, King H, New, David C, Wong, Yung H
Format: Article
Language:English
Subjects:
Amides - chemical synthesis
Amides - metabolism
Amides - pharmacology
Animals
CHO Cells
Cricetinae
Cricetulus
Drug Evaluation, Preclinical
Ligands
Melatonin - metabolism
Protein Binding
Receptor, Melatonin, MT2 - metabolism
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Summary:A series of substituted N-[3-(3-methoxyphenyl)propyl] amides were synthesized and their binding affinities towards human melatonin MT(1) and MT(2) receptors were evaluated. It was discovered that a benzyloxyl substituent incorporated at C6 position of the 3-methoxyphenyl ring dramatically enhanced the MT(2) binding affinity and at the same time decreased MT(1) binding affinity.
ISSN:1464-3405
DOI:10.1016/j.bmcl.2010.02.084