Synthesis, Structure Investigation and Evaluation of Anti-Orthopoxvirus Activity of 2-(2-arylethenyl)imidazoles | Sciact - CRIS-system of Boreskov Institute of Catalysis

Synthesis, Structure Investigation and Evaluation of Anti-Orthopoxvirus Activity of 2-(2-arylethenyl)imidazoles Full article

Journal

New Journal of Chemistry
ISSN: 1144-0546 , E-ISSN: 1369-9261

Output data

Year: 2025, DOI: 10.1039/d5nj03203b

Authors

Golfarb-Abramov Vladislav O. ¹ , Kazennova Anastasia V. ¹ , Basanova Elizaveta I. ¹ , Serova Olga A. ² , Bormotov Nikolai I. ² , Shishkina Larisa N. ² , Krasnov Vyacheslav I. ³ , Polovyanenko Dmitriy N. ³ , Moskalev Ivan A. ⁴ , Fedorov Alexey Yu. ⁴ , Arkhipov Sergey G. ⁴ , Ilyina Margarita G. ⁴ , Borisevich Sophia S. ⁴ , Yarovaya Olga I. ³ , Nikitina Polina A. ¹

Affiliations

1	Department of Fine Organic Synthesis and Chemistry of Dyes, D.I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, 125047, Moscow, Russia
2	State Research Center of Virology and Biotechnology VECTOR, Rospotrebnadzor, 630559, Koltsovo, Russia
3	N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Lavrentyev Ave., 9, 630090, Novosibirsk, Russia
4	SRF “SKIF”, 630559, Koltsovo, Russia

The continuing worldwide mpox outbreak (2022-present) provokes interest in the search for new small organic molecules possessing anti-viral activity against orthopoxviruses. In the course of this search a series of new 2-(2-arylethenyl)imidazoles was synthesized. Structural features of these derivatives were studied by means of NMR spectroscopy and single-crystal X-ray diffraction analysis. It was not surprising that all the title compounds were transisomers. Prevailing tautomers for 2-(2-arylethenyl)-1-hydroxyimidazoles were determined. If a carbonyl-containing substituent was present in position 5 of imidazole, then the compound existed predominantly in a N-hydroxy- tautomeric form both in the gaseous phase and in solution in polar aprotic solvents. In crystal either a single N-hydroxy-tautomer or a mixture of both tautomers (N-hydroxyimidazole and imidazole N-oxide) were observed. For 2-(2-arylethenyl)-1-hydroxy4,5-dimethylimidazoles in solution in polar aprotic solvents an equilibrium mixture of both tautomers in rapid interconversion was registered. Predominant conformers were determined for 1-hydroxyimidazoles, 1-methoxyimidazoles, 1-methylimidazole 3-oxides under consideration. Cytotoxicity and virus-inhibiting activity against Vaccinia virus were evaluated in vitro for all the imidazole derivatives under study. 2-(2-Arylethenyl)-1-methoxyimidazoles turned out to be the most promising. They also exhibited activities against such zoonotic orthopoxviruses as Cowpox virus and Mousepox (Ectromelia) virus. The lead compound 1-(1-methoxy-4-methyl-2-((E)-2-(4-nitrophenyl)ethenyl)-1Himidazol-5-yl)ethanone 4b demonstrated the highest selectivity index against Vaccinia virus (SI=305).

Golfarb-Abramov V.O. , Kazennova A.V. , Basanova E.I. , Serova O.A. , Bormotov N.I. , Shishkina L.N. , Krasnov V.I. , Polovyanenko D.N. , Moskalev I.A. , Fedorov A.Y. , Arkhipov S.G. , Ilyina M.G. , Borisevich S.S. , Yarovaya O.I. , Nikitina P.A.
Synthesis, Structure Investigation and Evaluation of Anti-Orthopoxvirus Activity of 2-(2-arylethenyl)imidazoles
New Journal of Chemistry. 2025. DOI: 10.1039/d5nj03203b WOS publication_identifier_short.sciact_skif_identifier_type

Web of science:	WOS:001606019200001
publication_identifier.sciact_skif_identifier_type:	4179

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