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

Nikolay A. Zefirov 1
Nikolay A. Zefirov
, 
Evgeniya Vladimirovna Nurieva 1
Evgeniya Vladimirovna Nurieva
, 
Ilia Andreevich Elisseev 1
Ilia Andreevich Elisseev
, 
Shokhrukh A. Khasanov 2
Shokhrukh A. Khasanov
, 
Maria A. Niukalova 2
Maria A. Niukalova
, 
Vladimir Victorovich Zarubaev 2
Vladimir Victorovich Zarubaev
, 
Ol'ga Nikolaevna Zefirova 1
Ol'ga Nikolaevna Zefirova
2 St. Petersburg Pasteur Institute, 197101 St. Petersburg, Russian Federation
10.71267/mencom.7570
Published 2025-01-24
Communication , Volume 35, Issue 1, 50-53
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Zefirov N. A. et al. New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 50-53.
GOST all authors (up to 50) Copy
Zefirov N. A., Nurieva E. V., Elisseev I. A., Khasanov S. A., Niukalova M. A., Zarubaev V. V., Zefirova O. N. New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study // Mendeleev Communications. 2025. Vol. 35. No. 1. pp. 50-53.
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TY - JOUR
DO - 10.71267/mencom.7570
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7570
TI - New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study
T2 - Mendeleev Communications
AU - Zefirov, Nikolay A.
AU - Nurieva, Evgeniya Vladimirovna
AU - Elisseev, Ilia Andreevich
AU - Khasanov, Shokhrukh A.
AU - Niukalova, Maria A.
AU - Zarubaev, Vladimir Victorovich
AU - Zefirova, Ol'ga Nikolaevna
PY - 2025
DA - 2025/01/24
PB - Mendeleev Communications
SP - 50-53
IS - 1
VL - 35
ER -
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@article{2025_Zefirov,
author = {Nikolay A. Zefirov and Evgeniya Vladimirovna Nurieva and Ilia Andreevich Elisseev and Shokhrukh A. Khasanov and Maria A. Niukalova and Vladimir Victorovich Zarubaev and Ol'ga Nikolaevna Zefirova},
title = {New adamantane-containing compounds targeting rimantadine-resistant influenza virus A/PR/8/34: molecular design, synthesis and SAR study},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7570},
number = {1},
pages = {50--53},
doi = {10.71267/mencom.7570}
}
MLA
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Zefirov, Nikolay A., et al. “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, Jan. 2025, pp. 50-53. https://mendcomm.colab.ws/publications/10.71267/mencom.7570.

Keywords

adamantane derivatives
heterocyclization
isothioureas
molecular docking
rimantadine resistant influenza virus
spiro compounds
structure�activity relationship (SAR).

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.

Funders

State assignment
AAAA-A21-121030200272-6

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