New carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane fragment as sugar moiety; Synthesis,X-ray crystallography and anticancer activity期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

New carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane fragment as sugar moiety; Synthesis,X-ray crystallography and anticancer activity

Affiliation:	1. University of Ottawa Institute of Mental Health Research, Ottawa, Ontario, Canada;2. Molecular Brain Research Group, Robarts Research Institute, University of Western Ontario, London, Ontario, Canada;3. Neuromorphological and Neuroendocrine Research Laboratory, Hungarian Academy of Sciences and Semmelweis University, Budapest, Hungary;4. Department of Clinical and Theoretical Mental Health, Semmelweis University, Budapest, Hungary;5. Institute of Neuroscience, Carleton University, Ottawa, Ontario, Canada;1. Department of Chemistry, University of Ulsan, Ulsan 680-749, Republic of Korea;2. Advanced Materials Divisions, Korea Research Institute of Chemical Technology, Daejeon 305-600, Republic of Korea;1. CPM, UMR 6226, Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France;2. Laboratoire MaSCE, UMR 6226, Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France

Abstract:	An amine group was synthesized starting from an optically active bicyclo[2.2.1]heptane compound, which was then used to build the 5 atoms ring of a key 6-chloropurine intermediate. This was then reacted with ammonia and selected amines obtaining new adenine- and 6-substituted adenine conformationally constrained carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane skeleton in the sugar moiety. X-ray crystallography confirmed an exo-coupling of base to the ring and a L configuration of the nucleoside analogues. The compounds were tested for anticancer activity.

Keywords:	Bicyclo[2.2.1]heptane nucleosides X-ray crystallography Anticancer Chloropurine Azide Amine
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