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New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study. / Zefirov, Nikolay A.; Nurieva, Evgeniya V.; Elisseev, Ilia A.; Khasanov, Shokhrukh A.; Niukalova, Maria A.; Zarubaev, Vladimir V.; Zefirova, Ol'ga Nikolaevna.

In: Mendeleev Communications, Vol. 35, No. 1, 01.01.2025, p. 50-53.

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

Harvard

Zefirov, NA, Nurieva, EV, Elisseev, IA, Khasanov, SA, Niukalova, MA, Zarubaev, VV & Zefirova, ON 2025, 'New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study', Mendeleev Communications, vol. 35, no. 1, pp. 50-53. https://doi.org/10.71267/mencom.7570, https://doi.org/10.71267/mencom.7570

APA

Zefirov, N. A., Nurieva, E. V., Elisseev, I. A., Khasanov, S. A., Niukalova, M. A., Zarubaev, V. V., & Zefirova, O. N. (2025). New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study. Mendeleev Communications, 35(1), 50-53. https://doi.org/10.71267/mencom.7570, https://doi.org/10.71267/mencom.7570

Vancouver

Zefirov NA, Nurieva EV, Elisseev IA, Khasanov SA, Niukalova MA, Zarubaev VV et al. New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study. Mendeleev Communications. 2025 Jan 1;35(1):50-53. https://doi.org/10.71267/mencom.7570, https://doi.org/10.71267/mencom.7570

Author

Zefirov, Nikolay A. ; Nurieva, Evgeniya V. ; Elisseev, Ilia A. ; Khasanov, Shokhrukh A. ; Niukalova, Maria A. ; Zarubaev, Vladimir V. ; Zefirova, Ol'ga Nikolaevna. / New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study. In: Mendeleev Communications. 2025 ; Vol. 35, No. 1. pp. 50-53.

BibTeX

@article{9f63fb92dd6a4fa99af30874127149e8,
title = "New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study",
abstract = "Four types of adamantane-containing compounds were designed by modifying molecules with proven activity against resistant influenza A viral strains or mutated M2 channel of the virion envelope. Three series were obtained, excluding 5'-methyl-5'H-spiro[adamantane-2,4'-thiazol]-2'-amine, since no intramolecular cyclization of 1-tert-butyl-3-(2-vinyladamantan-2-yl)thiourea occurred in the reaction with HBr or bromine. 2,7-Diazaspiro[3.5]nonane comprising derivatives of adamantane and new series of rimantadine amides have manifested high cytotoxicity, while acceptable selectivity was observed for ester analogues of the latter, and three novel esters demonstrated potent antiviral activity (IC50 = 1.5–12.6 µm vs. 67 µm for rimantadine) against the rimantadine-resistant influenza virus A/PR/8/34.",
keywords = "adamantane derivatives, heterocyclization, isothioureas, molecular docking, rimantadine resistant influenza virus, spiro compounds, structure–activity relationship (SAR)",
author = "Zefirov, {Nikolay A.} and Nurieva, {Evgeniya V.} and Elisseev, {Ilia A.} and Khasanov, {Shokhrukh A.} and Niukalova, {Maria A.} and Zarubaev, {Vladimir V.} and Zefirova, {Ol'ga Nikolaevna}",
year = "2025",
month = jan,
day = "1",
doi = "10.71267/mencom.7570",
language = "English",
volume = "35",
pages = "50--53",
journal = "Mendeleev Communications",
issn = "0959-9436",
publisher = "Elsevier",
number = "1",

}

RIS

TY - JOUR

T1 - New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study

AU - Zefirov, Nikolay A.

AU - Nurieva, Evgeniya V.

AU - Elisseev, Ilia A.

AU - Khasanov, Shokhrukh A.

AU - Niukalova, Maria A.

AU - Zarubaev, Vladimir V.

AU - Zefirova, Ol'ga Nikolaevna

PY - 2025/1/1

Y1 - 2025/1/1

N2 - Four types of adamantane-containing compounds were designed by modifying molecules with proven activity against resistant influenza A viral strains or mutated M2 channel of the virion envelope. Three series were obtained, excluding 5'-methyl-5'H-spiro[adamantane-2,4'-thiazol]-2'-amine, since no intramolecular cyclization of 1-tert-butyl-3-(2-vinyladamantan-2-yl)thiourea occurred in the reaction with HBr or bromine. 2,7-Diazaspiro[3.5]nonane comprising derivatives of adamantane and new series of rimantadine amides have manifested high cytotoxicity, while acceptable selectivity was observed for ester analogues of the latter, and three novel esters demonstrated potent antiviral activity (IC50 = 1.5–12.6 µm vs. 67 µm for rimantadine) against the rimantadine-resistant influenza virus A/PR/8/34.

AB - Four types of adamantane-containing compounds were designed by modifying molecules with proven activity against resistant influenza A viral strains or mutated M2 channel of the virion envelope. Three series were obtained, excluding 5'-methyl-5'H-spiro[adamantane-2,4'-thiazol]-2'-amine, since no intramolecular cyclization of 1-tert-butyl-3-(2-vinyladamantan-2-yl)thiourea occurred in the reaction with HBr or bromine. 2,7-Diazaspiro[3.5]nonane comprising derivatives of adamantane and new series of rimantadine amides have manifested high cytotoxicity, while acceptable selectivity was observed for ester analogues of the latter, and three novel esters demonstrated potent antiviral activity (IC50 = 1.5–12.6 µm vs. 67 µm for rimantadine) against the rimantadine-resistant influenza virus A/PR/8/34.

KW - adamantane derivatives

KW - heterocyclization

KW - isothioureas

KW - molecular docking

KW - rimantadine resistant influenza virus

KW - spiro compounds

KW - structure–activity relationship (SAR)

UR - https://www.mendeley.com/catalogue/bfb93254-a0e1-3214-8641-2a384f789045/

U2 - 10.71267/mencom.7570

DO - 10.71267/mencom.7570

M3 - Article

VL - 35

SP - 50

EP - 53

JO - Mendeleev Communications

JF - Mendeleev Communications

SN - 0959-9436

IS - 1

ER -

ID: 139418026