One-pot synthesis of new thiazole derivatives via the reaction of arylamines, carbon disulfide, and N-arylmaleimides and evaluations of their antiviral activity

One-pot synthesis of new thiazole derivatives via the reaction of arylamines, carbon disulfide, and N-arylmaleimides and evaluations of their antiviral activity Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2025, Volume: 74, Number: 4, Pages: 1120-1129 Pages count : 10 DOI: 10.1007/s11172-025-4605-7

Authors

Belokon A.A. ¹ , Stolpovskaya N.V. ¹ , Zorina A.V. ¹ , Pyankov O.V. ² , Prezent M.A. ³ , Minyaev M.E. ³ , Shikhaliev Kh.S. ¹

Affiliations

1	Voronezh State University, 1 Universitetskaya pl., 394018, Voronezh, Russian Federation
2	State Scientific Center of Virology and Biotechnology “Vector”, 630559, Koltsovo, Novosibirsk Region, Russian Federation
3	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

A one-pot reaction of arylamines with carbon disulfide and N-arylmaleimides at different ratios of reagents gave two types of substituted thiazolones: N-aryl-2-(3-aryl-4-oxo-2-thioxothiazolidin-5-yl)acetamides and N-aryl-2-(3-aryl-2-arylimino-4-oxothiazolidin-5-yl)acetamides. The reaction of arylamine with a small excess of carbon disulfide in acetonitrile led to N-aryldithiocarbamic acids, and treatment of the latter with N-arylmaleimides resulted in N-aryl-2-(3-aryl-4-oxo-2-thioxothiazolidin-5-yl)acetamides. The reaction of a twofold excess of arylamine with carbon disulfide in acetonitrile led to N1,N2-diarylthioureas, and treatment of the latter with N-arylmaleimides resulted in N-aryl-2-(3-aryl-2-arylimino-4-oxothiazolidin-5-yl)acetamides. A three-component mode at different ratios of N-arylmaleimide, arylamine, and carbon disulfide gave N-aryl-2-(3-aryl-4-oxo-2-thioxothiazolidin-5-yl)acetamides as the major reaction product. Evaluations of the antiviral activity of synthesized derivatives revealed that 2-[3-(4-methoxyphenyl)-4-oxo-2-thioxothiazolidin-5-yl]-N-(4-chlorophenyl)acetamide efficiently suppresses the replication of the SARS-CoV-2 virus.

Belokon A.A. , Stolpovskaya N.V. , Zorina A.V. , Pyankov O.V. , Prezent M.A. , Minyaev M.E. , Shikhaliev K.S.
One-pot synthesis of new thiazole derivatives via the reaction of arylamines, carbon disulfide, and N-arylmaleimides and evaluations of their antiviral activity
Russian Chemical Bulletin. 2025. V.74. N4. P.1120-1129. DOI: 10.1007/s11172-025-4605-7 WOS Scopus OpenAlex

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