title: Application of the bridgehead fragments for the design of conformationally restricted melatonin analogues.
abstract: Conformationally constrained analogues of the hormone melatonin with a side chain incorporated into the bicyclic bridgehead core were synthesized based on the homology modeling and molecular docking studies performed for the MT(2) melatonin receptor. The methoxy-indole derivative fused with exo-N-acetamino-substituted bicyclo[2.2.2]octane was found to possess nanomolar MT(2) receptor affinity.
authors.affiliation: Department of Chemistry, M.V. Lomonosov Moscow State University, Russian Federation. olgaz@org.chem.msu.ru
authors.forename: Olga N
authors.initials: ON
authors.lastname: Zefirova
authors.forename: Tatiana Yu
authors.initials: TY
authors.lastname: Baranova
authors.forename: Anna A
authors.initials: AA
authors.lastname: Ivanova
authors.forename: Andrei A
authors.initials: AA
authors.lastname: Ivanov
authors.forename: Nikolay S
authors.initials: NS
authors.lastname: Zefirov
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D003198:Computer Simulation; D007211:Indoles / Q000737:chemistry; D008550:Melatonin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008968:Molecular Conformation; D044122:Receptor, Melatonin, MT1 / Q000737:chemistry / Q000378:metabolism; D044123:Receptor, Melatonin, MT2 / Q000737:chemistry / Q000378:metabolism
chemical_list: D001643:Bridged Bicyclo Compounds; D007211:Indoles; D044122:Receptor, Melatonin, MT1; D044123:Receptor, Melatonin, MT2; C458301:bicyclo(3.3.1)nonane; C030374:indole; D008550:Melatonin