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F- and OH-Containing Isopulegol-Derived Octahydro-2H-Chromenes as Agents against Influenza A Virus †

Irina V. Ilyina
Oksana S. Patrusheva
Vladimir V. Zarubaev
Konstantin P. Volcho
1 and
Nariman F. Salakhutdinov
Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentjev av.9, 630090 Novosibirsk, Russia
Pasteur Institute of Epidemiology and Microbiology, 14 Mira str., 197101 St. Petersburg, Russia
Author to whom correspondence should be addressed.
Presented at the 1st International Electronic Conference on Molecular Sciences: Druggable Targets of Emerging Infectious Diseases (ECMS 2021), 1–14 September 2021; Available online:
Med. Sci. Forum 2021, 7(1), 12;
Published: 31 August 2021


Monoterpenes, which have a unique diverse structure and are inexpensive, available and often enantiomerically pure, are an attractive renewable raw material for the development of physiologically active agents. One of the most important methods for the utilization of monoterpenes is their interaction with carbonyl compounds, which produces heterocyclic compounds. Often these products exhibit analgesic, antiviral or neuroprotective properties. Earlier, we discovered the anti-influenza A (H1N1) virus activity of several compounds with a hydro-2H-chromene scaffold, which were synthesized by the Prins reaction using p-menthane alcohols and carbonyl compounds; montmorillonite K10 or nanosized halloysite catalyst were used as the reaction catalysts [1]. Chromenols produced from an (–)-isopulegol and aliphatic ketones (acetone and cyclopentanone) demonstrated a high activity combined with a low toxicity against the influenza virus [1]. The introduction of the fluorine atom into the molecule is an important strategy in the development of new biologically active compounds, enabling lipophilicity and electrostatic interactions to change and increasing the metabolic stability of compounds, which affects their physiological activity. Here, we synthesized fluoro- and hydroxy-containing octahydro-2H-chromenes by the Prins reaction starting from an (–)-isopulegol and a wide range of aromatic aldehydes in the presence of the BF3∙Et2O/H2O system, acting as both an acid catalyst and a fluorine source. The activity of the synthesized compounds against the influenza A/Puerto Rico/8/34 (H1N1) virus was studied. The highest activity was demonstrated by fluoro- and hydroxy-containing 2,4,6-trimethoxybenzaldehyde derivatives. These compounds were supposed to be capable of binding to viral hemagglutinin, which is an agreement with data on the effect of compounds on viral fusogenic activity, as well as with molecular docking studies.

Supplementary Materials

The following supporting information can be downloaded at:

Conflicts of Interest

The authors declare no conflict of interest.


  1. Salakhutdinov, N.; Volcho, K.; Yarovaya, O. Monoterpenes as a renewable source of biologically active compounds. Pure Appl. Chem. 2017, 89, 1105–1117. [Google Scholar] [CrossRef]
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MDPI and ACS Style

Ilyina, I.V.; Patrusheva, O.S.; Zarubaev, V.V.; Volcho, K.P.; Salakhutdinov, N.F. F- and OH-Containing Isopulegol-Derived Octahydro-2H-Chromenes as Agents against Influenza A Virus. Med. Sci. Forum 2021, 7, 12.

AMA Style

Ilyina IV, Patrusheva OS, Zarubaev VV, Volcho KP, Salakhutdinov NF. F- and OH-Containing Isopulegol-Derived Octahydro-2H-Chromenes as Agents against Influenza A Virus. Medical Sciences Forum. 2021; 7(1):12.

Chicago/Turabian Style

Ilyina, Irina V., Oksana S. Patrusheva, Vladimir V. Zarubaev, Konstantin P. Volcho, and Nariman F. Salakhutdinov. 2021. "F- and OH-Containing Isopulegol-Derived Octahydro-2H-Chromenes as Agents against Influenza A Virus" Medical Sciences Forum 7, no. 1: 12.

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