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Title: New carbocyclic N(6)-substituted adenine and pyrimidine nucleoside analogues with a bicyclo[2.2.1]heptane fragment as sugar moiety; synthesis, antiviral, anticancer activity and X-ray crystallography
Authors: Tănase, Constantin I
Drăghici, Constantin
Cojocaru, Ana
Galochkina, Anastasia V
Orshanskaya, Jana R
Shova, Sergiu
Enache, Cristian
Maganu, Maria
Zarubaev, Vladimir V. 
Keywords: Anticancer;Antiviral activity;Bicyclo[2.2.1]heptane nucleosides;Chloropurine;Pyrimidine nucleosides;X-ray-crystallography
Issue Date: 1-Oct-2015
Publisher: Elsevier
Journal: Bioorganic and Medicinal Chemistry 
Abstract: New nucleoside analogues with an optically active bicyclo[2.2.1]heptane skeleton as sugar moiety and 6-substituted adenine were synthesized by alkylation of 6-chloropurine intermediate. Thymine and uracil analogs were synthesized by building the pyrimidine ring on amine 1. X-ray crystallography confirmed an exo-coupling of the thymine to the ring and an L configuration of the nucleoside analogue. The library of compounds was tested for their inhibitory activity against influenza virus A∖California/07/09 (H1N1)pdm09 and coxsackievirus B4 in cell culture. Compounds 13a and 13d are the most promising for their antiviral activity against influenza, and compound 3c against coxsackievirus B4. Compounds 3b and 3g were tested for anticancer activity.
ISSN: 0968-0896
DOI: 10.1016/j.bmc.2015.08.033
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