Anti-influenza activity of monoterpene-containing substituted coumarins

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Anti-influenza activity of monoterpene-containing substituted coumarins. / Khomenko, Tatyana M.; Zarubaev, Vladimir V.; Orshanskaya, Iana R. et al.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 27, No. 13, 2017, p. 2920-2925.

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

Harvard

Khomenko, TM, Zarubaev, VV, Orshanskaya, IR, Kadyrova, RA, Sannikova, VA, Korchagina, DV, Volcho, KP & Salakhutdinov, NF 2017, 'Anti-influenza activity of monoterpene-containing substituted coumarins', Bioorganic and Medicinal Chemistry Letters, vol. 27, no. 13, pp. 2920-2925. https://doi.org/10.1016/j.bmcl.2017.04.091

APA

Khomenko, T. M., Zarubaev, V. V., Orshanskaya, I. R., Kadyrova, R. A., Sannikova, V. A., Korchagina, D. V., Volcho, K. P., & Salakhutdinov, N. F. (2017). Anti-influenza activity of monoterpene-containing substituted coumarins. Bioorganic and Medicinal Chemistry Letters, 27(13), 2920-2925. https://doi.org/10.1016/j.bmcl.2017.04.091

Vancouver

Khomenko TM, Zarubaev VV, Orshanskaya IR, Kadyrova RA, Sannikova VA, Korchagina DV et al. Anti-influenza activity of monoterpene-containing substituted coumarins. Bioorganic and Medicinal Chemistry Letters. 2017;27(13):2920-2925. doi: 10.1016/j.bmcl.2017.04.091

Author

Khomenko, Tatyana M. ; Zarubaev, Vladimir V. ; Orshanskaya, Iana R. et al. / Anti-influenza activity of monoterpene-containing substituted coumarins. In: Bioorganic and Medicinal Chemistry Letters. 2017 ; Vol. 27, No. 13. pp. 2920-2925.

BibTeX

@article{42965a0822504784b7dc1c537f1724e6,

title = "Anti-influenza activity of monoterpene-containing substituted coumarins",

abstract = "Compounds simultaneously carrying the monoterpene and coumarin moieties have been tested for cytotoxicity and inhibition of activity against influenza virus A/California/07/09 (H1N1)pdm09. The structure of substituents in the coumarin framework, as well as the structure and the absolute configuration of the monoterpenoid moiety, are shown to significantly influence the anti-influenza activity and cytotoxicity of the compounds under study. The compounds with a bicyclic pinane framework exhibit the highest selectivity indices (the ratios between the cytotoxicity and the active dose). The derivative of (−)-myrtenol 15c, which is characterized by promising activity, low cytotoxicity, and synthetic accessibility, has the greatest potential among this group of compounds. It exhibited the highest activity when added to the infected cell culture at early stages of viral reproduction.",

keywords = "Anti-influenza activity, Antivirals, Aurapten, Coumarin, Cytotoxicity, Influenza A virus, Myrtenal, Terpene, Madin Darby Canine Kidney Cells/drug effects, Antiviral Agents/chemical synthesis, Virus Replication/drug effects, Cells, Cultured, Models, Molecular, Structure-Activity Relationship, Coumarins/chemical synthesis, Dose-Response Relationship, Drug, Microbial Sensitivity Tests, Animals, Influenza A Virus, H1N1 Subtype/drug effects, Monoterpenes/chemistry, Dogs, Cell Death/drug effects, Molecular Structure, DESIGN, COMPOUND, DRUG DISCOVERY, FRAGMENTS, PROGRESS, INFLUENZA-A VIRUSES, NEURAMINIDASE INHIBITORS, PINANAMINE DERIVATIVES, IN-VIVO, ANTIVIRAL ACTIVITY",

author = "Khomenko, {Tatyana M.} and Zarubaev, {Vladimir V.} and Orshanskaya, {Iana R.} and Kadyrova, {Renata A.} and Sannikova, {Victoria A.} and Korchagina, {Dina V.} and Volcho, {Konstantin P.} and Salakhutdinov, {Nariman F.}",

year = "2017",

doi = "10.1016/j.bmcl.2017.04.091",

language = "English",

volume = "27",

pages = "2920--2925",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "13",

}

RIS

TY - JOUR

T1 - Anti-influenza activity of monoterpene-containing substituted coumarins

AU - Khomenko, Tatyana M.

AU - Zarubaev, Vladimir V.

AU - Orshanskaya, Iana R.

AU - Kadyrova, Renata A.

AU - Sannikova, Victoria A.

AU - Korchagina, Dina V.

AU - Volcho, Konstantin P.

AU - Salakhutdinov, Nariman F.

PY - 2017

Y1 - 2017

N2 - Compounds simultaneously carrying the monoterpene and coumarin moieties have been tested for cytotoxicity and inhibition of activity against influenza virus A/California/07/09 (H1N1)pdm09. The structure of substituents in the coumarin framework, as well as the structure and the absolute configuration of the monoterpenoid moiety, are shown to significantly influence the anti-influenza activity and cytotoxicity of the compounds under study. The compounds with a bicyclic pinane framework exhibit the highest selectivity indices (the ratios between the cytotoxicity and the active dose). The derivative of (−)-myrtenol 15c, which is characterized by promising activity, low cytotoxicity, and synthetic accessibility, has the greatest potential among this group of compounds. It exhibited the highest activity when added to the infected cell culture at early stages of viral reproduction.

AB - Compounds simultaneously carrying the monoterpene and coumarin moieties have been tested for cytotoxicity and inhibition of activity against influenza virus A/California/07/09 (H1N1)pdm09. The structure of substituents in the coumarin framework, as well as the structure and the absolute configuration of the monoterpenoid moiety, are shown to significantly influence the anti-influenza activity and cytotoxicity of the compounds under study. The compounds with a bicyclic pinane framework exhibit the highest selectivity indices (the ratios between the cytotoxicity and the active dose). The derivative of (−)-myrtenol 15c, which is characterized by promising activity, low cytotoxicity, and synthetic accessibility, has the greatest potential among this group of compounds. It exhibited the highest activity when added to the infected cell culture at early stages of viral reproduction.

KW - Anti-influenza activity

KW - Antivirals

KW - Aurapten

KW - Coumarin

KW - Cytotoxicity

KW - Influenza A virus

KW - Myrtenal

KW - Terpene

KW - Madin Darby Canine Kidney Cells/drug effects

KW - Antiviral Agents/chemical synthesis

KW - Virus Replication/drug effects

KW - Cells, Cultured

KW - Models, Molecular

KW - Structure-Activity Relationship

KW - Coumarins/chemical synthesis

KW - Dose-Response Relationship, Drug

KW - Microbial Sensitivity Tests

KW - Animals

KW - Influenza A Virus, H1N1 Subtype/drug effects

KW - Monoterpenes/chemistry

KW - Dogs

KW - Cell Death/drug effects

KW - Molecular Structure

KW - DESIGN

KW - COMPOUND

KW - DRUG DISCOVERY

KW - FRAGMENTS

KW - PROGRESS

KW - INFLUENZA-A VIRUSES

KW - NEURAMINIDASE INHIBITORS

KW - PINANAMINE DERIVATIVES

KW - IN-VIVO

KW - ANTIVIRAL ACTIVITY

UR - http://www.scopus.com/inward/record.url?scp=85019144448&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2017.04.091

DO - 10.1016/j.bmcl.2017.04.091

M3 - Article

C2 - 28501512

AN - SCOPUS:85019144448

VL - 27

SP - 2920

EP - 2925

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 13

ER -

ID: 8969200