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Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses. / Ilyina, Irina V.; Zarubaev, Vladimir V.; Lavrentieva, Irina N. et al.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 28, No. 11, 15.06.2018, p. 2061-2067.

Research output: Contribution to journal › Article › peer-review

Harvard

Ilyina, IV, Zarubaev, VV, Lavrentieva, IN, Shtro, AA, Esaulkova, IL, Korchagina, DV, Borisevich, SS, Volcho, KP & Salakhutdinov, NF 2018, 'Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses', Bioorganic and Medicinal Chemistry Letters, vol. 28, no. 11, pp. 2061-2067. https://doi.org/10.1016/j.bmcl.2018.04.057

APA

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. (2018). Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses. Bioorganic and Medicinal Chemistry Letters, 28(11), 2061-2067. https://doi.org/10.1016/j.bmcl.2018.04.057

Vancouver

Ilyina IV, Zarubaev VV, Lavrentieva IN, Shtro AA, Esaulkova IL, Korchagina DV et al. Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses. Bioorganic and Medicinal Chemistry Letters. 2018 Jun 15;28(11):2061-2067. doi: 10.1016/j.bmcl.2018.04.057

Author

Ilyina, Irina V. ; Zarubaev, Vladimir V. ; Lavrentieva, Irina N. et al. / Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses. In: Bioorganic and Medicinal Chemistry Letters. 2018 ; Vol. 28, No. 11. pp. 2061-2067.

BibTeX

@article{269daa1e618c4641aa61c9db0bcd9c51,
title = "Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses",
abstract = "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.",
keywords = "Antiviral, Chromene, Influenza, Monoterpene, Montmorillonite K10, MONOTERPENOIDS, HEMAGGLUTININ, ANALGESIC ACTIVITY, DISCOVERY, PRINS CYCLIZATION, ANTIINFLUENZA ACTIVITY, ANTIVIRAL ACTIVITY, DERIVATIVES, Antiviral Agents/chemical synthesis, Structure-Activity Relationship, Dose-Response Relationship, Drug, Microbial Sensitivity Tests, Influenza A virus/drug effects, Terpenes/chemical synthesis, Influenza B virus/drug effects, Molecular Structure",
author = "Ilyina, {Irina V.} and Zarubaev, {Vladimir V.} and Lavrentieva, {Irina N.} and Shtro, {Anna A.} and Esaulkova, {Iana L.} and Korchagina, {Dina V.} and Borisevich, {Sophia S.} and Volcho, {Konstantin P.} and Salakhutdinov, {Nariman F.}",
note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",
year = "2018",
month = jun,
day = "15",
doi = "10.1016/j.bmcl.2018.04.057",
language = "English",
volume = "28",
pages = "2061--2067",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Ltd",
number = "11",

}

RIS

TY - JOUR

T1 - Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses

AU - Ilyina, Irina V.

AU - Zarubaev, Vladimir V.

AU - Lavrentieva, Irina N.

AU - Shtro, Anna A.

AU - Esaulkova, Iana L.

AU - Korchagina, Dina V.

AU - Borisevich, Sophia S.

AU - Volcho, Konstantin P.

AU - Salakhutdinov, Nariman F.

N1 - Publisher Copyright: © 2018 Elsevier Ltd

PY - 2018/6/15

Y1 - 2018/6/15

N2 - 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.

AB - 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.

KW - Antiviral

KW - Chromene

KW - Influenza

KW - Monoterpene

KW - Montmorillonite K10

KW - MONOTERPENOIDS

KW - HEMAGGLUTININ

KW - ANALGESIC ACTIVITY

KW - DISCOVERY

KW - PRINS CYCLIZATION

KW - ANTIINFLUENZA ACTIVITY

KW - ANTIVIRAL ACTIVITY

KW - DERIVATIVES

KW - Antiviral Agents/chemical synthesis

KW - Structure-Activity Relationship

KW - Dose-Response Relationship, Drug

KW - Microbial Sensitivity Tests

KW - Influenza A virus/drug effects

KW - Terpenes/chemical synthesis

KW - Influenza B virus/drug effects

KW - Molecular Structure

UR - http://www.scopus.com/inward/record.url?scp=85046140063&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2018.04.057

DO - 10.1016/j.bmcl.2018.04.057

M3 - Article

C2 - 29716780

AN - SCOPUS:85046140063

VL - 28

SP - 2061

EP - 2067

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 11

ER -

ID: 12948756