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Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity. / Chernyshov, Vladimir V.; Yarovaya, Olga I.; Fadeev, Dmitry S. et al.

In: Molecular Diversity, Vol. 24, No. 1, 01.02.2020, p. 61-67.

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

Harvard

Chernyshov, VV, Yarovaya, OI, Fadeev, DS, Gatilov, YV, Esaulkova, YL, Muryleva, AS, Sinegubova, KO, Zarubaev, VV & Salakhutdinov, NF 2020, 'Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity', Molecular Diversity, vol. 24, no. 1, pp. 61-67. https://doi.org/10.1007/s11030-019-09932-9

APA

Chernyshov, V. V., Yarovaya, O. I., Fadeev, D. S., Gatilov, Y. V., Esaulkova, Y. L., Muryleva, A. S., Sinegubova, K. O., Zarubaev, V. V., & Salakhutdinov, N. F. (2020). Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity. Molecular Diversity, 24(1), 61-67. https://doi.org/10.1007/s11030-019-09932-9

Vancouver

Chernyshov VV, Yarovaya OI, Fadeev DS, Gatilov YV, Esaulkova YL, Muryleva AS et al. Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity. Molecular Diversity. 2020 Feb 1;24(1):61-67. doi: 10.1007/s11030-019-09932-9

Author

Chernyshov, Vladimir V. ; Yarovaya, Olga I. ; Fadeev, Dmitry S. et al. / Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity. In: Molecular Diversity. 2020 ; Vol. 24, No. 1. pp. 61-67.

BibTeX

@article{366113223a344f0aaddf29628138c453,
title = "Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity",
abstract = "An effective technique for one-stage synthesis of new polycyclic nitrogen-containing compounds has been developed. The procedure involves refluxing mixtures of camphoric acid with aliphatic or aromatic diamine without catalysts. In cases where the starting amine has a low boiling point (less than 200 °C), phenol is used as a solvent, as it is the most optimal one for obtaining products with good yields. It has been shown that the use of Lewis acids as catalysts reduces the yield of the reaction products. A set of compounds have been synthesized, which can be attributed to synthetic analogues of alkaloids. In vitro screening for activity influenza virus A was carried out for the obtained compounds. The synthesized quinazoline-like agent 14 has inhibitory activity against different strains of influenza viruses.",
keywords = "(+)-Camphoric acid, Alkaloid analogues, Antiviral activity, Antivirals, Influenza virus, Single-stage synthesis, ARBIDOL, INHIBITION, INFLUENZA-A VIRUS, LIGANDS, DIETHYLZINC, CHEMISTRY, RESISTANCE, DERIVATIVES, VASICINE",
author = "Chernyshov, {Vladimir V.} and Yarovaya, {Olga I.} and Fadeev, {Dmitry S.} and Gatilov, {Yuriy V.} and Esaulkova, {Yana L.} and Muryleva, {Anna S.} and Sinegubova, {Katherina O.} and Zarubaev, {Vladimir V.} and Salakhutdinov, {Nariman F.}",
note = "Publisher Copyright: {\textcopyright} 2019, Springer Nature Switzerland AG. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",
year = "2020",
month = feb,
day = "1",
doi = "10.1007/s11030-019-09932-9",
language = "English",
volume = "24",
pages = "61--67",
journal = "Molecular Diversity",
issn = "1381-1991",
publisher = "Springer Netherlands",
number = "1",

}

RIS

TY - JOUR

T1 - Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity

AU - Chernyshov, Vladimir V.

AU - Yarovaya, Olga I.

AU - Fadeev, Dmitry S.

AU - Gatilov, Yuriy V.

AU - Esaulkova, Yana L.

AU - Muryleva, Anna S.

AU - Sinegubova, Katherina O.

AU - Zarubaev, Vladimir V.

AU - Salakhutdinov, Nariman F.

N1 - Publisher Copyright: © 2019, Springer Nature Switzerland AG. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/2/1

Y1 - 2020/2/1

N2 - An effective technique for one-stage synthesis of new polycyclic nitrogen-containing compounds has been developed. The procedure involves refluxing mixtures of camphoric acid with aliphatic or aromatic diamine without catalysts. In cases where the starting amine has a low boiling point (less than 200 °C), phenol is used as a solvent, as it is the most optimal one for obtaining products with good yields. It has been shown that the use of Lewis acids as catalysts reduces the yield of the reaction products. A set of compounds have been synthesized, which can be attributed to synthetic analogues of alkaloids. In vitro screening for activity influenza virus A was carried out for the obtained compounds. The synthesized quinazoline-like agent 14 has inhibitory activity against different strains of influenza viruses.

AB - An effective technique for one-stage synthesis of new polycyclic nitrogen-containing compounds has been developed. The procedure involves refluxing mixtures of camphoric acid with aliphatic or aromatic diamine without catalysts. In cases where the starting amine has a low boiling point (less than 200 °C), phenol is used as a solvent, as it is the most optimal one for obtaining products with good yields. It has been shown that the use of Lewis acids as catalysts reduces the yield of the reaction products. A set of compounds have been synthesized, which can be attributed to synthetic analogues of alkaloids. In vitro screening for activity influenza virus A was carried out for the obtained compounds. The synthesized quinazoline-like agent 14 has inhibitory activity against different strains of influenza viruses.

KW - (+)-Camphoric acid

KW - Alkaloid analogues

KW - Antiviral activity

KW - Antivirals

KW - Influenza virus

KW - Single-stage synthesis

KW - ARBIDOL

KW - INHIBITION

KW - INFLUENZA-A VIRUS

KW - LIGANDS

KW - DIETHYLZINC

KW - CHEMISTRY

KW - RESISTANCE

KW - DERIVATIVES

KW - VASICINE

UR - http://www.scopus.com/inward/record.url?scp=85062589474&partnerID=8YFLogxK

U2 - 10.1007/s11030-019-09932-9

DO - 10.1007/s11030-019-09932-9

M3 - Article

C2 - 30820742

AN - SCOPUS:85062589474

VL - 24

SP - 61

EP - 67

JO - Molecular Diversity

JF - Molecular Diversity

SN - 1381-1991

IS - 1

ER -

ID: 18815774