Synthesis of 4‐(5‐Amino‐1,3,4‐thiadiazol‐2‐yl)pyrrolidin‐2‐ones and Their Antifungal Activity

Synthesis of 4‐(5‐Amino‐1,3,4‐thiadiazol‐2‐yl)pyrrolidin‐2‐ones and Their Antifungal Activity Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2025, Volume: 10, Number: 36, Article number : e03719, Pages count : DOI: 10.1002/slct.202503719

Authors

Serkov Sergei A. ¹ , Sigay Natalya V. ¹ , Kostikova Natalya N. ¹ , Alekseenko Anna L. ² , Kolotyrkina Natalya G. ¹ , Popkov Sergey V. ² , Gazieva Galina A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky Prosp. Moscow 119991 Russian Federation
2	Faculty of Chemical‐Pharmaceutical Technologies and Biomedical Preparations D. I. Mendeleev University of Chemical Technology of Russia 9 Miusskaya Sq. Moscow 125047 Russian Federation

A novel series of 1-aryl- and 1-alkyl-4-(5-amino-1,3,4-thiadiazol-2-yl)pyrrolidin-2-ones was synthesized by the condensation of 1-aryl- or 1-alkyl-5-oxopyrrolidine-3-carboxylic acids and thiosemicarbazide upon heating with concentrated sulfuric acid and characterized using IR, 1H NMR, 13C NMR, and HRMS spectral data. The proposed approach was suitable for the synthesis of some 4-(5-amino-1,3,4-thiadiazol-2-yl)-1-heteroarylpyrrolidin-2-ones. The protocol ensures the stability of the pyrrolidinone cycle under reaction conditions. The synthesized compounds showed significant antifungal activity against phytopathogens R. solani and V. inaequalis. Two the most active compounds, 4-(5-amino-1,3,4-thiadiazol-2-yl)-1-(4-chlorobenzyl)pyrrolidin-2-one and 4-(5-amino-1,3,4-thiadiazol-2-yl)-1-(6-nitrobenzothiazol-2-yl)pyrrolidin-2-one, also showed moderate activity against B. sorokiniana. They inhibited the mycelial growth of R.solani, V. inaequalis and B. sorokiniana by 100, 60-78, and 53-55%, respectively, which is higher than that of the reference compound triadimefon (43%, 41%, and 44%, respectively).

Serkov S.A. , Sigay N.V. , Kostikova N.N. , Alekseenko A.L. , Kolotyrkina N.G. , Popkov S.V. , Gazieva G.A.
Synthesis of 4‐(5‐Amino‐1,3,4‐thiadiazol‐2‐yl)pyrrolidin‐2‐ones and Their Antifungal Activity
ChemistrySelect. 2025. V.10. N36. e03719 . DOI: 10.1002/slct.202503719 WOS Scopus OpenAlex

≡ Web of science:	WOS:001576612700001
≡ Scopus:	2-s2.0-105016800221
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