Diels–Alder Adducts of  N -Substituted 2-Pyridones with Maleinimides. Synthesis and Antiviral Activity

V. A. Sorokina; Сорокина В. А.; A. V. Kovalskaya; Ковальская А. В.; A. N. Lobov; Лобов А. Н.; P. A. Ilyina; Ильина П. А.; V. V. Zarubaev; Зарубаев В. В.; I. P. Tsypysheva; Цыпышева И. П.

doi:10.31857/S0044460X24060024

Diels–Alder Adducts of N-Substituted 2-Pyridones with Maleinimides. Synthesis and Antiviral Activity

Authors: Sorokina V.A.¹, Kovalskaya A.V.¹, Lobov A.N.¹, Ilyina P.A.², Zarubaev V.V.², Tsypysheva I.P.¹
Affiliations:
1. Ufa Federal Research Center of the Russian Academy of Sciences
2. Saint Petersburg Pasteur Institute
Issue: Vol 94, No 6 (2024)
Pages: 691-698
Section: Articles
URL: https://journals.rcsi.science/0044-460X/article/view/269848
DOI: https://doi.org/10.31857/S0044460X24060024
EDN: https://elibrary.ru/FAESAH
ID: 269848

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Abstract

Adducts of N-substituted 2-pyridones [pyridine-2(1H)-ones] and N-substituted maleic acid imides were synthesized under thermal conditions of the Diels–Alder reaction with yields from 68 to 97%. Cytotoxicity and antiviral activity of the obtained compounds were studied using a model of adenovirus infection [human adenovirus type 5 (AdV5)] in MA-104 cell culture. It was shown that the synthesized adducts have low toxicity and medium antiviral activity. Only 9-hexyl-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-(epiminomethano)isoindole-1,3,8-trione has the most pronounced viral inhibitory properties with a selectivity index of 7.

Keywords

Diels–Alder reaction, 2-pyridone, antiviral activity, human adenovirus type 5 (AdV5)

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