Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses

Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses Full article

Journal

Bioorganic and Medicinal Chemistry Letters
ISSN: 0960-894X , E-ISSN: 1464-3405

Output data

Year: 2018, Volume: 28, Number: 11, Pages: 2061-2067 Pages count : 7 DOI: 10.1016/j.bmcl.2018.04.057

Tags

Influenza; Antiviral; Monoterpene; Chromene; Montmorillonite K10

Authors

Ilyina Irina, V ^1,2 , Zarubaev Vladimir V. ³ , Lavrentieva Irina N. ³ , Shtro Anna A. ⁴ , Esaulkova Iana L. ⁵ , Korchagina Dina, V ¹ , Borisevich Sophia S. ⁶ , Volcho Konstantin P. ^1,2 , Salakhutdinov Nariman F. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Novosibirsk Inst Organ Chem, Siberian Branch, Lavrentjev Av 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Pasteur Inst Epidemiol & Microbiol, 14 Mira Str, St Petersburg 197101, Russia
4	(Данные Web of science) Influenza Res Inst, Dept Preclin Trials, 15-17 Prof Popova St, St Petersburg 197376, Russia
5	(Данные Web of science) St Petersburg State Univ, 7-9 Univ Skaya Nab, St Petersburg 199034, Russia
6	(Данные Web of science) Ufa Fed Res Ctr, Ufa Chem Inst, Lab Chem Phys, 71 Octyabrya Pr, Ufa 450054, Russia

A set of (-)-isopulegol derived octahydro-2H-chromen-4-ols was synthesized and evaluated in vitro for antiviral activity against panel of reference influenza virus strains differing in subtype, origin (human or avian) and drug resistance. Compound (4R)-11a produced via one-pot synthesis by interaction between (-)-isopulegol and acetone was found to exhibit an outstanding activity against a number of H1N1 and H2N2 influenza virus strains with selectivity index more than 1500. (4R)-11a was shown to be most potent at early stages of viral cycle. Good correlation between anti-viral activity and calculated binding energy to hemagglutinin TBHQ active site was demonstrated. (C) 2018 Elsevier Ltd. All rights reserved.

Ilyina I.V. , Zarubaev V.V. , Lavrentieva I.N. , Shtro A.A. , Esaulkova I.L. , Korchagina D.V. , Borisevich S.S. , Volcho K.P. , Salakhutdinov N.F.
Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses
Bioorganic and Medicinal Chemistry Letters. 2018. V.28. N11. P.2061-2067. DOI: 10.1016/j.bmcl.2018.04.057 WOS Scopus РИНЦ

Published print:

Jun 1, 2018

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