Synthesis and structure-activity relationship of novel benzoxazole derivatives as melatonin receptor agonists

• Published in: Bioorganic & medicinal chemistry letters Vol. 14; no. 14; pp. 3799 - 3802
• Main Authors: SUN, Li-Qiang, JIE CHEN, CEN XU, BRUCE, Marc, DESKUS, Jeffrey A, EPPERSON, James R, TAKAKI, Katherine, JOHNSON, Graham, IBEN, Lawrence, MAHLE, Cathy D, RYAN, Elaine
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier 16.07.2004
• Subjects: Benzoxazoles - chemical synthesis; Benzoxazoles - pharmacology; Binding Sites; Biological and medical sciences; Cell Line; Contrast media. Radiopharmaceuticals; Drug Design; Humans; Ligands; Medical sciences; Melatonin - analogs & derivatives; Melatonin - metabolism; Neuropharmacology; Neurotransmitters. Neurotransmission. Receptors; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems; Pharmacology. Drug treatments; Radioligand Assay; Receptors, Cell Surface - drug effects; Receptors, Melatonin - agonists; Receptors, Melatonin - metabolism; Structure-Activity Relationship; Agonist; Iodine 125; Radiolabelling; Iodine Isotopes; In vitro; Structure activity relation; Bicyclic compound; Affinity; Aromatic compound; MT2 melatonin receptor; MT1 melatonin receptor; Chemical synthesis; Oxygen nitrogen heterocycle
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2004.04.082

A series of benzoxazole derivatives was synthesized and evaluated as melatoninergic ligands. The binding affinity of these compounds for human MT(1) and MT(2) receptors was determined using 2-[(125)I]-iodomelatonin as the radioligand. From this series of benzoxazole derivatives, compounds 14 and 17 were identified as melatonin receptor agonists.