title: N-Acetyl-5-arylalkoxytryptamine analogs: probing the melatonin receptors for MT(1) -selectivity.
abstract: A series of melatonin analogs obtained by the replacement of the ether methyl group with larger arylalkyl and aryloxyalkyl substituents was prepared in order to probe the melatonin receptors for MT(1) -selectivity. The most MT(1) -selective agents 11 and 15 were substituted with a Ph(CH(2) )(3)  or a PhO(CH(2) )(3)  group. Compounds 11 and 15 displayed 11.5-fold and 11-fold higher affinity for the MT(1)  receptors than for the MT(2)  subtype. Interestingly, in our binding assay 11 and 15 have shown considerably higher MT(1) -affinity and selectivity than the reference ligand, the dimeric agomelatine 1a.
authors: Institute of Pharmacy and Food Chemistry, Pharmaceutical Chemistry, University of Würzburg, Germany.
authors: Christian
authors: C
authors: Markl
authors: William P
authors: WP
authors: Clafshenkel
authors: Mohamed I
authors: MI
authors: Attia
authors: Shalini
authors: S
authors: Sethi
authors: Paula A
authors: PA
authors: Witt-Enderby
authors: Darius P
authors: DP
authors: Zlotos
mesh_terms: D000818:Animals; D001667:Binding, Competitive; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D006801:Humans; D007457:Iodine Radioisotopes; D008024:Ligands; D008550:Melatonin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011485:Protein Binding; D011869:Radioligand Assay; D044122:Receptor, Melatonin, MT1 / Q000235:genetics / Q000378:metabolism*; D044123:Receptor, Melatonin, MT2 / Q000235:genetics / Q000378:metabolism
chemical_list: D007457:Iodine Radioisotopes; D008024:Ligands; D044122:Receptor, Melatonin, MT1; D044123:Receptor, Melatonin, MT2; D008550:Melatonin