Derivatives of (–)-Cytisine with Thiourea Fragment. Synthesis and Antiviral Activity

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

doi:10.31857/S0044460X24060054

Derivatives of (–)-Cytisine with Thiourea Fragment. Synthesis and Antiviral Activity

Authors: Kovalskaya A.V.¹, Lobov A.N.¹, 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: 712-721
Section: Articles
URL: https://journals.rcsi.science/0044-460X/article/view/269852
DOI: https://doi.org/10.31857/S0044460X24060054
EDN: https://elibrary.ru/EZGYGT
ID: 269852

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Abstract

New derivatives of the quinolizidine alkaloid, (–)-cytisine, with a substituted 2-pyridone ring and a thiourea moiety in the bispidin fragment of the molecule were synthesized. The ability of the synthesized cytisine-containing thioureas to inhibit the reproduction of human parainfluenza virus type 3 was assessed. It was found that the derivatives obtained by the reaction of benzoyl or phenyl isothiocyanate with (–)-cytisine, as well as its 9-bromo or 9,11-derivative, effectively suppress the reproduction of human parainfluenza virus type 3 (their selectivity indices are 56, 58 and 95, respectively), which confirms the promise of the chosen approach to synthetic modifications of the alkaloid (–)-cytisine in order to obtain effective antiviral agents on its basis.

Keywords

(–)-cytisine, thiourea, cytotoxicity, antiviral activity, human parainfluenza virus type 3 (HPIV3)

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