Synthesis of camphecene derivatives using click chemistry methodology and study of their antiviral activity

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

    Research output: Contribution to journalArticlepeer-review

    14 Citations (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)2181-2184
    Number of pages4
    JournalBioorganic and Medicinal Chemistry Letters
    Volume27
    Issue number10
    DOIs
    Publication statusPublished - 15 May 2017

    Keywords

    • Acetylenes
    • Antivirals
    • Azides
    • Camphor
    • Click chemistry
    • Imine derivatives
    • Influenza
    • Triazoles
    • AZIDE-ALKYNE CYCLOADDITION
    • DESIGN
    • DISCOVERY
    • 1,2,3-TRIAZOLES
    • INHIBITORS
    • INFLUENZA-VIRUS ENTRY
    • Antiviral Agents/chemical synthesis
    • Click Chemistry
    • Humans
    • Structure-Activity Relationship
    • Ethanolamines/chemical synthesis
    • Animals
    • Influenza A Virus, H1N1 Subtype/drug effects
    • Camphor/analogs & derivatives
    • Dogs
    • Madin Darby Canine Kidney Cells

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