Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors

Bioorganic & Medicinal Chemistry
2010.0

Abstract

A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT(1) and MT(2) receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists.

Knowledge Graph

Similar Paper

Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors
Bioorganic & Medicinal Chemistry 2010.0
N-(Substituted-anilinoethyl)amides: Design, Synthesis, and Pharmacological Characterization of a New Class of Melatonin Receptor Ligands
Journal of Medicinal Chemistry 2007.0
Synthesis and Structure−Affinity−Activity Relationships of Novel Benzofuran Derivatives as MT<sub>2</sub> Melatonin Receptor Selective Ligands
Journal of Medicinal Chemistry 2002.0
Design and synthesis of 1-(2-alkanamidoethyl)-6-methoxy-7-azaindole derivatives as potent melatonin agonists
Bioorganic &amp; Medicinal Chemistry Letters 2011.0
Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT2-selective melatonin ligands
Bioorganic &amp; Medicinal Chemistry Letters 2010.0
Synthesis and pharmacological evaluation of 1,2,3,4-tetrahydropyrazino[1,2-a]indole and 2-[(phenylmethylamino)methyl]-1H-indole analogues as novel melatoninergic ligands
Bioorganic &amp; Medicinal Chemistry 2009.0
Preparation and pharmacological evaluation of a novel series of 2-(phenylthio)benzo[b]thiophenes as selective MT2 receptor ligands
European Journal of Medicinal Chemistry 2011.0
Design and Synthesis ofN-(3,3-Diphenylpropenyl)alkanamides as a Novel Class of High-Affinity MT<sub>2</sub>-Selective Melatonin Receptor Ligands
Journal of Medicinal Chemistry 2006.0
Design and synthesis of 3-phenyltetrahydronaphthalenic derivatives as new selective MT2 melatoninergic ligands. Part II
Bioorganic &amp; Medicinal Chemistry 2009.0
New melatonin (MT1/MT2) ligands: Design and synthesis of (8,9-dihydro-7H-furo[3,2-f]chromen-1-yl) derivatives
Bioorganic &amp; Medicinal Chemistry 2014.0