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 the MT(2) binding affinity and at the same time decreased MT(1) binding affinity.
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.
Yueqing
Y
Hu
Maurice K C
MK
Ho
King H
KH
Chan
David C
DC
New
Yung H
YH
Wong
D000577:Amides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D004353:Drug Evaluation, Preclinical; D008024:Ligands; D008550:Melatonin / Q000378:metabolism*; D011485:Protein Binding; D044123:Receptor, Melatonin, MT2 / Q000378:metabolism*
D000577:Amides; D008024:Ligands; D044123:Receptor, Melatonin, MT2; D008550:Melatonin