Design and synthesis of 2-phenylimidazo[1,2-a]pyridines as a novel class of melatonin receptor ligands.

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El Kazzouli S, Griffon du Bellay A, Berteina-Raboin S, Delagrange P, Caignard DH, Guillaumet G

Design and synthesis of 2-phenylimidazo[1,2-a]pyridines as a novel class of melatonin receptor ligands.

Eur J Med Chem. 2011 Sep;46(9):4252-7. doi: 10.1016/j.ejmech.2011.06.030. Epub 2011 Jul 1.

PubMed ID

21764185 [ View in PubMed

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Abstract

A novel class of imidazo[1,2-a]pyridines as melatonin receptor ligands is designed and synthesized. The affinities of 3-(6-methoxy-2-phenylimidazo[1,2-a]pyridine-3-yl)-N-methyl-propionamide 8, N-[2-(6-methoxy-2-phenylimidazo[1,2-a]pyridine-3-yl)-ethyl]-acetamide 13 and N-(1-hydroxy-3-(5-methoxy-2-phenyl-1H-indol-3-yl)propan-2-yl)acetamide 18 are evaluated for binding on melatonin receptors. Compound 8 present good selectivity for MT(2) over MT(1) (MT(1)/MT(2) = 19) and compound 13 have good affinities for both MT(1) (Ki :28 nM) and MT(2) (Ki : 8 nM).

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Melatonin	Melatonin receptor type 1A	Ki (nM)	0.25	N/A	N/A	Details
Melatonin	Melatonin receptor type 1B	Ki (nM)	0.34	N/A	N/A	Details