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.
Hu
Yueqing
Y
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.
Ho
Maurice K C
MK
Chan
King H
KH
New
David C
DC
Wong
Yung H
YH
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