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Synthesis and structure-activity relationships of novel camphecene analogues as anti-influenza agents. / Yarovaya, Olga I.; Sokolova, Anastasiya S.; Mainagashev, Iliya Ya et al.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 29, No. 23, 126745, 01.12.2019.

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

Harvard

Yarovaya, OI, Sokolova, AS, Mainagashev, IY, Volobueva, AS, Lantseva, K, Borisevich, SS, Shtro, AA, Zarubaev, VV & Salakhutdinov, NF 2019, 'Synthesis and structure-activity relationships of novel camphecene analogues as anti-influenza agents', Bioorganic and Medicinal Chemistry Letters, vol. 29, no. 23, 126745. https://doi.org/10.1016/j.bmcl.2019.126745

APA

Yarovaya, O. I., Sokolova, A. S., Mainagashev, I. Y., Volobueva, A. S., Lantseva, K., Borisevich, S. S., Shtro, A. A., Zarubaev, V. V., & Salakhutdinov, N. F. (2019). Synthesis and structure-activity relationships of novel camphecene analogues as anti-influenza agents. Bioorganic and Medicinal Chemistry Letters, 29(23), [126745]. https://doi.org/10.1016/j.bmcl.2019.126745

Vancouver

Yarovaya OI, Sokolova AS, Mainagashev IY, Volobueva AS, Lantseva K, Borisevich SS et al. Synthesis and structure-activity relationships of novel camphecene analogues as anti-influenza agents. Bioorganic and Medicinal Chemistry Letters. 2019 Dec 1;29(23):126745. doi: 10.1016/j.bmcl.2019.126745

Author

Yarovaya, Olga I. ; Sokolova, Anastasiya S. ; Mainagashev, Iliya Ya et al. / Synthesis and structure-activity relationships of novel camphecene analogues as anti-influenza agents. In: Bioorganic and Medicinal Chemistry Letters. 2019 ; Vol. 29, No. 23.

BibTeX

@article{4675961d53bb4c1caf35b39e00596b9a,
title = "Synthesis and structure-activity relationships of novel camphecene analogues as anti-influenza agents",
abstract = "A chemical library was constructed based on the scaffold of camphecene (2-(E)-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene-aminoethanol). The modifications included introduction of mono-and bicyclic heterocyclic moieties in place of the terminal hydroxyl group of camphecene. All compounds were tested for cytotoxicity and anti-viral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells. Among 15 tested compounds 11 demonstrated a selectivity index (SI) higher than 10 and IC50 values in the micromolar range. The antiviral activity and toxicity were shown to strongly depend on the nature of the heterocyclic substituent. Compounds 2 and 14 demonstrated the highest virus-inhibiting activity with SIs of 106 and 183, and bearing pyrrolidine and piperidine moieties, correspondingly. Compound 14 was shown to interfere with viral reproduction at early stages of the viral life cycle (0–2 h post-infection). Taken together, our data suggest potential of camphecene derivatives in particular and camphor-based imine derivatives in general as effective anti-influenza compounds.",
keywords = "Antivirals, Camphecene, Camphor, Imine derivatives, Influenza, IN-VITRO, INHIBITORS, DERIVATIVES, DISCOVERY, VIRUSES",
author = "Yarovaya, {Olga I.} and Sokolova, {Anastasiya S.} and Mainagashev, {Iliya Ya} and Volobueva, {Alexandrina S.} and Khristina Lantseva and Borisevich, {Sophia S.} and Shtro, {Anna A.} and Zarubaev, {Vladimir V.} and Salakhutdinov, {Nariman F.}",
note = "Publisher Copyright: {\textcopyright} 2019",
year = "2019",
month = dec,
day = "1",
doi = "10.1016/j.bmcl.2019.126745",
language = "English",
volume = "29",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Ltd",
number = "23",

}

RIS

TY - JOUR

T1 - Synthesis and structure-activity relationships of novel camphecene analogues as anti-influenza agents

AU - Yarovaya, Olga I.

AU - Sokolova, Anastasiya S.

AU - Mainagashev, Iliya Ya

AU - Volobueva, Alexandrina S.

AU - Lantseva, Khristina

AU - Borisevich, Sophia S.

AU - Shtro, Anna A.

AU - Zarubaev, Vladimir V.

AU - Salakhutdinov, Nariman F.

N1 - Publisher Copyright: © 2019

PY - 2019/12/1

Y1 - 2019/12/1

N2 - A chemical library was constructed based on the scaffold of camphecene (2-(E)-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene-aminoethanol). The modifications included introduction of mono-and bicyclic heterocyclic moieties in place of the terminal hydroxyl group of camphecene. All compounds were tested for cytotoxicity and anti-viral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells. Among 15 tested compounds 11 demonstrated a selectivity index (SI) higher than 10 and IC50 values in the micromolar range. The antiviral activity and toxicity were shown to strongly depend on the nature of the heterocyclic substituent. Compounds 2 and 14 demonstrated the highest virus-inhibiting activity with SIs of 106 and 183, and bearing pyrrolidine and piperidine moieties, correspondingly. Compound 14 was shown to interfere with viral reproduction at early stages of the viral life cycle (0–2 h post-infection). Taken together, our data suggest potential of camphecene derivatives in particular and camphor-based imine derivatives in general as effective anti-influenza compounds.

AB - A chemical library was constructed based on the scaffold of camphecene (2-(E)-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene-aminoethanol). The modifications included introduction of mono-and bicyclic heterocyclic moieties in place of the terminal hydroxyl group of camphecene. All compounds were tested for cytotoxicity and anti-viral activity against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells. Among 15 tested compounds 11 demonstrated a selectivity index (SI) higher than 10 and IC50 values in the micromolar range. The antiviral activity and toxicity were shown to strongly depend on the nature of the heterocyclic substituent. Compounds 2 and 14 demonstrated the highest virus-inhibiting activity with SIs of 106 and 183, and bearing pyrrolidine and piperidine moieties, correspondingly. Compound 14 was shown to interfere with viral reproduction at early stages of the viral life cycle (0–2 h post-infection). Taken together, our data suggest potential of camphecene derivatives in particular and camphor-based imine derivatives in general as effective anti-influenza compounds.

KW - Antivirals

KW - Camphecene

KW - Camphor

KW - Imine derivatives

KW - Influenza

KW - IN-VITRO

KW - INHIBITORS

KW - DERIVATIVES

KW - DISCOVERY

KW - VIRUSES

UR - http://www.scopus.com/inward/record.url?scp=85074404068&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2019.126745

DO - 10.1016/j.bmcl.2019.126745

M3 - Article

C2 - 31668423

AN - SCOPUS:85074404068

VL - 29

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 23

M1 - 126745

ER -

ID: 22087534