Synthesis and pharmacological evaluation of pentacyclic 6a,7-dihydrodiindole and 2,3-dihydrodiindole derivatives as novel melatoninergic ligands

Bioorganic & Medicinal Chemistry
2008.0

Abstract

The synthesis of novel melatonin analogues 3a and 4a-c designed as melatonin receptor ligands is described. Among the newly synthesized ligands, 2-((S)-2-hydroxymethylindolin-1-ylmethyl)-melatonin 4b displayed the highest affinity for MT(1) receptors (K(i)=9.8 nM) and for MT(2) subtype (K(i)=7.8 nM), whereas the rigid pentacyclic ligand 3 showed the highest selectivity towards the MT(2) receptor subtype (K(i)=319.3 nM for MT(1) and K(i)=65.2 nM for MT(2)).

Knowledge Graph

Similar Paper

Synthesis and pharmacological evaluation of pentacyclic 6a,7-dihydrodiindole and 2,3-dihydrodiindole derivatives as novel melatoninergic ligands
Bioorganic & Medicinal Chemistry 2008.0
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
2-[(1,3-Dihydro-2H-isoindol-2-yl)methyl]melatonin – a novel MT2-selective melatonin receptor antagonist
MedChemComm 2011.0
Synthesis of Nitroindole Derivatives with High Affinity and Selectivity for Melatoninergic Binding Sites MT<sub>3</sub>
Journal of Medicinal Chemistry 2002.0
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
Design and synthesis of 1-(2-alkanamidoethyl)-6-methoxy-7-azaindole derivatives as potent melatonin agonists
Bioorganic &amp; Medicinal Chemistry Letters 2011.0
1,6-Dihydro-2H-indeno[5,4-b]furan Derivatives: Design, Synthesis, and Pharmacological Characterization of a Novel Class of Highly Potent MT<sub>2</sub>-Selective Agonists
Journal of Medicinal Chemistry 2011.0
Design, synthesis and pharmacological evaluation of novel naphthalenic derivatives as selective MT1 melatoninergic ligands
Bioorganic &amp; Medicinal Chemistry 2010.0
2-[(2,3-Dihydro-1H-indol-1-yl)methyl]melatonin Analogues: A Novel Class of MT<sub>2</sub>-Selective Melatonin Receptor Antagonists
Journal of Medicinal Chemistry 2009.0
Synthesis of 3-phenylnaphthalenic derivatives as new selective MT2 melatoninergic ligands
Bioorganic &amp; Medicinal Chemistry 2008.0