Synthesis of new melatoninergic hexahydroindenopyridines |
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| Institution: | 1. Departamento de Farmacología, Laboratorio de Farmacoquímica, Facultad de Farmacia, Universidad de Valencia, 46100 Burjassot, Valencia, Spain;2. Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Málaga, 29071 Málaga, Spain;3. Départament des Sciences Expérimentales, Institut de Recherches Servier, 92150 Suresnes, France;4. UMR CNRS 8076, LERMIT, Université Paris-Sud, Laboratoire de Pharmacognosie, UFR de Pharmacie, Châtenay-Malabry F-92296, France;5. Centro de Ecología Química Agrícola-Instituto Agroforestal Mediterraneo, UPV, Campus de Vera, Edificio 6C, 46022 Valencia, Spain;1. Molecular Probe Program, Molecular Imaging Center, National Institute of Radiological Sciences, 4-9-1 Anagawa, Inage-ku, Chiba 263-8555, Japan;2. SHI Accelerator Service Co. Ltd, 5-9-11 Kitashinagawa, Shinagawa-ku, Tokyo 141-8686, Japan;1. School of Pharmacy, University of the Western Cape, Private Bag X17, Bellville 7535, South Africa;2. Division of Clinical Pharmacology, Department of Medicine, University of Cape Town, Groote Schuur Hospital, Observatory 7925, South Africa;1. Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Zhejiang Normal University, 321004, PR China;2. College of Chemical and Life Science, Zhejiang Normal University, 321004, PR China;1. Faculty of Chemistry, Silesian University of Technology, Strzody 9, 44-100 Gliwice, Poland;2. ARC Centre of Excellence for Electromaterials Science, Intelligent Polymer Research Institute, University of Wollongong, Northfields Avenue, Wollongong, NSW 2522 Australia;3. Institute of Physics, Silesian University of Technology, B. Krzywoustego 2, 44-100 Gliwice, Poland;4. Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland;5. Center of Polymer and Carbon Materials, Polish Academy of Science, Sowinskiego 5, 44-100 Gliwice, Poland;1. ICTM-Center for Chemistry, University of Belgrade, Njego?eva 12, 11000 Belgrade, Serbia;2. Faculty of Chemistry University of Belgrade, Studentski trg 12-16, 11158 Belgrade, Serbia |
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| Abstract: | Hexahydroindenopyridine (HHIP) is an interesting heterocyclic framework that contains an indene core similar to ramelteon. This type of tricyclic piperidines aroused our interest as potential melatoninergic ligands. Melatonin receptor ligands have applications in insomnia and depression. We report herein an efficient two-step method to prepare new HHIP by the reaction of an enamine with 3-bromopropylamine hydrobromide. Some synthesized compounds showed moderate affinity for melatonin receptors in the nanomolar or low micromolar range. Furthermore, the methylenedioxy HHIPs 2d (N-phenylacetamide) and 2f (N,N-diethylacetamide), exhibited high selectivity at MT1 or MT2 receptors, respectively, when compared with melatonin. It seems that the methylenedioxy group on the indene ring system and the N-acetamide substituent are important structural features to bind selectively MT1 or MT2 subtypes. |
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| Keywords: | Hexahydroindenopyridines Melatonin Receptor binding Synthesis |
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