( R)-2-(4-Phenylbutyl)dihydrobenzofuran derivatives as melatoninergic agents

• Published in: Bioorganic & medicinal chemistry letters Vol. 15; no. 5; pp. 1345 - 1349
• Main Authors: Sun, Li-Qiang, Takaki, Katherine, Chen, Jie, Bertenshaw, Stephen, Iben, Lawrence, Mahle, Cathy D., Ryan, Elaine, Wu, Dedong, Gao, Qi, Xu, Cen
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.03.2005; Elsevier
• Subjects: Animals; Benzofurans - chemical synthesis; Benzofurans - chemistry; Benzofurans - pharmacology; Biological and medical sciences; Cloning, Molecular; Dihydrobenzofuran; Humans; Ligands; Medical sciences; Melatonin; Melatonin - agonists; Melatonin - pharmacology; Melatonin receptors; Melatoninergic agents; Mice; Molecular Structure; Neuropharmacology; Neurotransmitters. Neurotransmission. Receptors; NIH 3T3 Cells; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems; Pharmacology. Drug treatments; Protein Binding - drug effects; Rats; Receptor, Melatonin, MT1 - drug effects; Receptor, Melatonin, MT1 - metabolism; Receptor, Melatonin, MT2 - drug effects; Receptor, Melatonin, MT2 - metabolism; Recombinant Proteins - drug effects; Recombinant Proteins - metabolism; Structure-Activity Relationship; Vasoconstriction - drug effects; Vasoconstrictor Agents - chemical synthesis; Vasoconstrictor Agents - chemistry; Vasoconstrictor Agents - pharmacology; Melatonin receptors; Dihydrobenzofuran; Melatonin; Melatoninergic agents; Human; Cyclopropane derivatives; Aliphatic compound; Ligand; Oxygen heterocycle; In vitro; Biological fixation; Structure activity relation; Bicyclic compound; Affinity; Carboxamide; Ureas; Aromatic compound; Chemical synthesis; Melatonin receptor
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2005.01.015

( R)-2-(4-Phenylbutyl)dihydrobenzofuran derivatives (e.g., 3 and 4) were synthesized as novel melatoninergic ligands with significantly lower vasoconstrictive activity in vitro in the rat tail artery. Binding affinity assays were performed on cloned human MT 1 and MT 2 receptors stably expressed in NIH3T3 cells. ( R)-2-(4-Phenylbutyl)dihydrobenzofuran derivatives (e.g., 3 and 4) were synthesized as novel melatoninergic ligands with significantly lower vasoconstrictive activity in vitro in the rat tail artery. Binding affinity assays were performed on cloned human MT 1 and MT 2 receptors stably expressed in NIH3T3 cells.