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Camphor-based symmetric diimines as inhibitors of influenza virus reproduction.

Bioorganic & medicinal chemistry (2014-03-19)
Anastasiya S Sokolova, O Cyrilliclga I Yarovaya, Dina V Korchagina, Vladimir V Zarubaev, Tatiana S Tretiak, Pavel M Anfimov, Oleg I Kiselev, Nariman F Salakhutdinov

Influenza is a continuing world-wide public health problem that causes significant morbidity and mortality during seasonal epidemics and sporadic pandemics. The purpose of the study was synthesis and investigation of antiviral activity of camphor-based symmetric diimines and diamines. A set of C2-symmetric nitrogen-containing camphor derivatives have been synthesized. The antiviral activity of these compounds was studied against rimantadine- and amantadine-resistant influenza virus A/California/7/09 (H1N1)pdm09 in MDCK cells. The highest efficacy in virus inhibiting was shown for compounds 2a-e with cage moieties bound by aliphatic linkers. The therapeutic index (selectivity index) for 2b exceeded that for reference compounds amantadine, deitiforin and rimantadine almost 10-fold. As shown by structure-activity analysis, the length of the linker has a dramatic effect on the toxicity of compounds. Compound 2e with -C12H24- linker exhibited the lowest toxicity (CTD50=2216μM). Derivatives of camphor, therefore, can be considered as prospective antiinfluenza compounds active against influenza viruses resistant to adamantane-based drugs.

Product Number
Product Description

(±)-Camphor, meets analytical specification of Ph. Eur., BP, ≥95% (GC), racemic