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

Yueqing Hu; Maurice K C Ho; King H Chan; David C New; Yung H Wong

doi:10.1016/j.bmcl.2010.02.084

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

Bioorg Med Chem Lett. 2010 Apr 15;20(8):2582-5. doi: 10.1016/j.bmcl.2010.02.084. Epub 2010 Feb 25.

Authors

Yueqing Hu¹, Maurice K C Ho, King H Chan, David C New, Yung H Wong

Affiliation

¹ Department of Biochemistry, the Biotechnology Research Institute, and the Molecular Neuroscience Centre, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong.

PMID: 20227878
DOI: 10.1016/j.bmcl.2010.02.084

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemical synthesis*
Amides / metabolism
Amides / pharmacology*
Animals
CHO Cells
Cricetinae
Cricetulus
Drug Evaluation, Preclinical
Ligands
Melatonin / metabolism*
Protein Binding
Receptor, Melatonin, MT2 / metabolism*

Substances

Amides
Ligands
Receptor, Melatonin, MT2
Melatonin