Anti-infectives (Track)


Grishko V. , Tolmacheva I., Galayko N. and Igosheva E 

Institute of Technical Chemistry of Ural Branch of the Russian Academy of Sciences, 614013, Russian Federation, Perm, Acad. Korolev St., 3


Among triterpene derivatives, compounds featured by inhibiting action towards enveloped viruses were found. The most impressive achievement in this field is the synthesis of super-low-dose antiretrovirus compound Bevirimat, obtained by etherification of betulinic acid with 2,2- dimethylsuccinic acid [1]. Some of natural and semi-synthetic A-secotriterpenoids have been described as promising anti-HIV agents [2].

We have synthesized 3-oxo-2-oxime of betulonic acid, efficiently suppressing (EC50 0.03-6.3 mcg/ml) HIV-1 and influenza A viruses reproduction.

3-Oxo-2-oxime was used as a key intermediate to prepare 2,3-secolupane triterpenoids. A range of derivatives featured by high anti-viral activity towards HIV-1 (EC50 0.03-3.8 mcg/ml), herpes simplex virus (EC50 2.2-26.7 mcg/ml) and Ainfluenza virus (EC50 8.8-12.9 mcg/ml) was produced using the targeted modification method.

It has been ascertained that functionalization of 2,3-secotriterpene structures by pharmacophoric groups enables discovering antiviral agents combining anti-HIV activity and anti-influenza or anti-herpes properties.

The research work was financially supported by State contract (No. 11.519.11.2033), RFBR Grant No. 13-03-00629 and subsidy of the research projects «IRG».

Keywords: A-secotriterpenoids, betulonic acid, antiviral activity, flu A virus, herpes simplex virus, HIV-I.


[1] Kashiwada Y., Hashimoto F., Cosentino L.M., Chen C.H., Garrett P. E., Lee K.H. J. Med. Chem. 1996. V. 39. P. 1016–1017.

[2] Wei Y., Ma C.-M., Hattori ??. Bioorgan. Med. Chem. 2009. V. 17. P. 3003–3010.