Design and synthesis of 1-(2-alkanamidoethyl)-6-methoxy-7-azaindole derivatives as potent melatonin agonists

Bioorganic & Medicinal Chemistry Letters
2011.0

Abstract

A series of 7-azaindolic ligands bearing a methoxy group and a N-acetyl chain as melatoninergic pharmacophores were synthesized and their binding affinities towards MT(1) and MT(2) receptors were evaluated. Compounds 7a-c and 12 (cyclohexyl ring connected at C-2 and C-3 position) appears as important melatonin MT(2) and MT(1) receptors agonists. On the other hand, the presence of basic groups (amines) at position C-3 was detrimental to the melatoninergic affinities.

Knowledge Graph

Similar Paper

Design and synthesis of 1-(2-alkanamidoethyl)-6-methoxy-7-azaindole derivatives as potent melatonin agonists
Bioorganic & Medicinal Chemistry Letters 2011.0
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 & Medicinal Chemistry 2009.0
Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors
Bioorganic & Medicinal Chemistry 2010.0
Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT2-selective melatonin ligands
Bioorganic & Medicinal Chemistry Letters 2010.0
1-(2-Alkanamidoethyl)-6-methoxyindole Derivatives:  A New Class of Potent Indole Melatonin Analogues
Journal of Medicinal Chemistry 1997.0
Synthesis of a Novel Series of Benzocycloalkene Derivatives as Melatonin Receptor Agonists
Journal of Medicinal Chemistry 2002.0
Synthesis and structure–activity relationship of novel benzoxazole derivatives as melatonin receptor agonists
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis and pharmacological evaluation of pentacyclic 6a,7-dihydrodiindole and 2,3-dihydrodiindole derivatives as novel melatoninergic ligands
Bioorganic & Medicinal Chemistry 2008.0
Mapping the Melatonin Receptor. 6. Melatonin Agonists and Antagonists Derived from 6H-Isoindolo[2,1-a]indoles, 5,6-Dihydroindolo[2,1-a]isoquinolines, and 6,7-Dihydro-5H-benzo[c]azepino[2,1-a]indoles
Journal of Medicinal Chemistry 2000.0
Design and synthesis of benzoxazole derivatives as novel melatoninergic ligands
Bioorganic & Medicinal Chemistry Letters 2004.0