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Lelyukh M, Chaban I, Lysiuk R, Savchenko A, Yelahina N, Martyniuk D, et al . Synthesis and In Vitro Antitrypanosomal Evaluation of 2-Hydrazino-4-Thiazolidinones Containing 6-Phenylimidazo[2,1-b][1,3,4]thiadiazole Moiety. pbp 2026; 8 (1)
URL: http://pbp.medilam.ac.ir/article-1-356-en.html
URL: http://pbp.medilam.ac.ir/article-1-356-en.html
Maryan Lelyukh *1 
, Ihor Chaban2 , Roman Lysiuk2 
, Arkadii Savchenko2 , Nataliia Yelahina3 , Daria Martyniuk4 , Olexandra Komarytsya2 , Taras Chaban5
, Ihor Chaban2 , Roman Lysiuk2 , Arkadii Savchenko2 , Nataliia Yelahina3 , Daria Martyniuk4 , Olexandra Komarytsya2 , Taras Chaban5
1- Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine , lelyukh.m@gmail.com
2- Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine
3- Lugansk State Medical University, 16 Lypnya St. 36, Rivne 33017, Ukraine
4- Rivne Scientific Research Forensic Center of Ministry of Internal Affairs of Ukraine, V. Chervoniya, St. 39, Rivne, 33000, Ukraine
5- Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine 2Lugansk State Medical University, 16 Lypnya St. 36, Rivne 33017, Ukraine
2- Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine
3- Lugansk State Medical University, 16 Lypnya St. 36, Rivne 33017, Ukraine
4- Rivne Scientific Research Forensic Center of Ministry of Internal Affairs of Ukraine, V. Chervoniya, St. 39, Rivne, 33000, Ukraine
5- Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine 2Lugansk State Medical University, 16 Lypnya St. 36, Rivne 33017, Ukraine
Abstract: (24 Views)
Objective: A convenient and effective method for the obtaining of a 4-thiazolidinone ring is the [2+3]-cyclocondensation reaction of S,N-binucleophiles with different equivalents of the dielectrophilic synthon [C2]2+. For this purpose, we achieved the synthesis of intermediate N1-methylidenethiosemicarbazones 3a-b starting from 2-amino/allylsulfanyl-5-ethyl-1,3,4-thiadiazoles 1-b via Vilsmeier-Haak formylation reaction following by condensation with thiosemicarbazide in acetic acid medium.
Methods: Organic Synthesis, NMR Spectroscopy, Elemental analysis, Pharmacological screening.
Results: The interaction of intermediate N1-methylidenethiosemicarbazones 3a-b with α-halocarboxylic (monochloroacetic, 2-bromopropionic, 2-bromobutanoic) acids or α-bromo-γ-butyrolactone in acetic acid at the presence of sodium acetate was performed. As results, a series of targeted 2-hydrazino-4-thiazolidinones containing 6-phenylimidazo[2,1-b][1,3,4]thiadiazole moiety 4a-b and their 5-alkyl substituted derivatives 5a-d and 6a-b were obtained. The structure of the synthesized compounds was confirmed by elemental analysis and NMR spectroscopy. The synthesized compounds 3a-b, 4a-b, 5a-d, and 6a-b were evaluated for their in vitro antitrypanosomal activity against Trypanosoma brucei gambiense (Feo strain).
Conclusion. The results of in vitro screening of antitrypanosomal activity against Trypanosoma brucei gambiense (TBG) allowed us to identify three highly active compounds 4b, 5b and 5c, which exhibited significant trypanocidal activity with a range of IC50 values of 3.7-4.4 µM and were comparable to the reference drug nifurtimox (IC50 = 4.4 µM).
Methods: Organic Synthesis, NMR Spectroscopy, Elemental analysis, Pharmacological screening.
Results: The interaction of intermediate N1-methylidenethiosemicarbazones 3a-b with α-halocarboxylic (monochloroacetic, 2-bromopropionic, 2-bromobutanoic) acids or α-bromo-γ-butyrolactone in acetic acid at the presence of sodium acetate was performed. As results, a series of targeted 2-hydrazino-4-thiazolidinones containing 6-phenylimidazo[2,1-b][1,3,4]thiadiazole moiety 4a-b and their 5-alkyl substituted derivatives 5a-d and 6a-b were obtained. The structure of the synthesized compounds was confirmed by elemental analysis and NMR spectroscopy. The synthesized compounds 3a-b, 4a-b, 5a-d, and 6a-b were evaluated for their in vitro antitrypanosomal activity against Trypanosoma brucei gambiense (Feo strain).
Conclusion. The results of in vitro screening of antitrypanosomal activity against Trypanosoma brucei gambiense (TBG) allowed us to identify three highly active compounds 4b, 5b and 5c, which exhibited significant trypanocidal activity with a range of IC50 values of 3.7-4.4 µM and were comparable to the reference drug nifurtimox (IC50 = 4.4 µM).
Keywords: 2-Hydrazono-4-thiazolidinones, Imidazo[2, 1-b][1, 3, 4]thiadiazoles, Heterocyclization Reaction, Spectral Data, Antitrypanosomal Activity
Type of Study: Research |
Subject:
Phytomedicine
Received: 2025/09/23 | Accepted: 2026/01/29 | Published: 2026/01/29
Received: 2025/09/23 | Accepted: 2026/01/29 | Published: 2026/01/29
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