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N ‐Acetyl‐5‐arylalkoxytryptamine Analogs: Probing the Melatonin Receptors for MT 1 ‐Selectivity
Author(s) -
Markl Christian,
Clafshenkel William P.,
Attia Mohamed I.,
Sethi Shalini,
WittEnderby Paula A.,
Zlotos Darius P.
Publication year - 2011
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201100125
Subject(s) - selectivity , chemistry , receptor , melatonin , melatonin receptor , ligand (biochemistry) , stereochemistry , ether , biochemistry , organic chemistry , biology , endocrinology , catalysis
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 .