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Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity
Authors:Oleg I Artyushin  Elena V Sharova  Natalya M Vinogradova  Galina K Genkina  Aleksandra A Moiseeva  Zinaida S Klemenkova  Iana R Orshanskaya  Anna A Shtro  Renata A Kadyrova  Vladimir V Zarubaev  Olga I Yarovaya  Nariman F Salakhutdinov  Valery K Brel
Institution:1. A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 28, Vavilova St., GSP-1, V-334, 119991 Moscow, Russian Federation;2. Department of Chemotherapy, Influenza Research Institute, 15/17 Prof. Popova St., 197376 St. Petersburg, Russian Federation;3. Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentjev Avenue 9, 630090 Novosibirsk, Russian Federation;4. Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation
Abstract:A series of seventeen tetrazole derivatives of 1,7,7-trimethyl-2.2.1]bicycloheptane were synthesized using click chemistry methodology and characterized by spectral data. Studies of cytotoxicity and in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells of the compounds obtained were performed. The structure-activity relationship analysis suggests that to possess virus-inhibiting activity, the compounds of this group should bear oxygen atom with a short linker (C2-C4), either as a hydroxyl group (18, 19, 29), keto-group (21) or as a part of a heterocycle (24). These compounds demonstrated low cytotoxicity along with high anti-viral activity.
Keywords:Acetylenes  Antivirals  Azides  Camphor  Click chemistry  Imine derivatives  Influenza  Triazoles
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