Rimantadine derivatives with antiviral activity against flaviviruses and rimantadine-resistant strain of influenza A virus
N A Zefirov
1
,
E V Khvatov
2
,
E V Nurieva
1
,
Ya L Esaulkova
3
,
A. S. Volobueva
3
,
V V Zarubaev
3
,
A S Goryashchenko
2
,
D. O. Yatsenko
2
,
V I Uvarova
2
,
D I Osolodkin
2
,
A A Ishmukhametov
2
,
O N Zefirova
1
Publication type: Journal Article
Publication date: 2024-06-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
Abstract
Pyridine-containing amides of rimantadine (1-(1-adamantyl)ethylamine) were synthesized by the amidation of rimantadine hydrochloride by the corresponding acids in the NEt3—N,N′-dicyclohexylcarbodiimide (DCC)—4-(N,N-dimethylamino)pyridine (DMAP) system as the analogues of previously described antiviral compounds 1-adamantylmethyl-5-aminoisoxazole-3-carboxylate and N-{[5-(thien-2-yl)isoxazol-3-yl]methyl}adamantane-1-amine. The spectrum of antiviral activity against the rimantadine-resistant A/PR/8/34 strain of influenza A virus, tick-borne encephalitis virus (TBEV) strain Absettarov (European subtype), yellow fever virus (YFV) vaccine strain 17D, and West Nile virus (WNV) strain Strix nebulosa-12 was studied. The structure—activity relationships were discussed. Synthesized compounds efficiently inhibited the reproduction of TBEV and WNV. N-[1-(Adamantan-1-yl)ethyl]picolinamide efficiently inhibited the reproduction of enveloped viruses with both type I (influenza) and type II (flaviviruses) fusion proteins. The antiviral activity against the rimantadine-resistant influenza virus A/PR/8/34 and a low cytotoxicity (high selectivity index) were revealed for N-[1-(adamantan-1-yl)ethyl]-isonicotinamide.
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Zefirov N. A. et al. Rimantadine derivatives with antiviral activity against flaviviruses and rimantadine-resistant strain of influenza A virus // Russian Chemical Bulletin. 2024. Vol. 73. No. 6. pp. 1801-1810.
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Zefirov N. A., Khvatov E. V., Nurieva E. V., Esaulkova Ya. L., Volobueva A. S., Zarubaev V. V., Goryashchenko A. S., Yatsenko D. O., Uvarova V. I., Osolodkin D. I., Ishmukhametov A. A., Zefirova O. N. Rimantadine derivatives with antiviral activity against flaviviruses and rimantadine-resistant strain of influenza A virus // Russian Chemical Bulletin. 2024. Vol. 73. No. 6. pp. 1801-1810.
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TY - JOUR
DO - 10.1007/s11172-024-4297-4
UR - https://link.springer.com/10.1007/s11172-024-4297-4
TI - Rimantadine derivatives with antiviral activity against flaviviruses and rimantadine-resistant strain of influenza A virus
T2 - Russian Chemical Bulletin
AU - Zefirov, N A
AU - Khvatov, E V
AU - Nurieva, E V
AU - Esaulkova, Ya L
AU - Volobueva, A. S.
AU - Zarubaev, V V
AU - Goryashchenko, A S
AU - Yatsenko, D. O.
AU - Uvarova, V I
AU - Osolodkin, D I
AU - Ishmukhametov, A A
AU - Zefirova, O N
PY - 2024
DA - 2024/06/01
PB - Springer Nature
SP - 1801-1810
IS - 6
VL - 73
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2024_Zefirov,
author = {N A Zefirov and E V Khvatov and E V Nurieva and Ya L Esaulkova and A. S. Volobueva and V V Zarubaev and A S Goryashchenko and D. O. Yatsenko and V I Uvarova and D I Osolodkin and A A Ishmukhametov and O N Zefirova},
title = {Rimantadine derivatives with antiviral activity against flaviviruses and rimantadine-resistant strain of influenza A virus},
journal = {Russian Chemical Bulletin},
year = {2024},
volume = {73},
publisher = {Springer Nature},
month = {jun},
url = {https://link.springer.com/10.1007/s11172-024-4297-4},
number = {6},
pages = {1801--1810},
doi = {10.1007/s11172-024-4297-4}
}
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MLA
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Zefirov, N. A., et al. “Rimantadine derivatives with antiviral activity against flaviviruses and rimantadine-resistant strain of influenza A virus.” Russian Chemical Bulletin, vol. 73, no. 6, Jun. 2024, pp. 1801-1810. https://link.springer.com/10.1007/s11172-024-4297-4.