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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
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: (152 Views)
Objective: A convenient and efficient method for constructing the 4-thiazolidinone ring is the [2+3]-cyclocondensation reaction of S,N-binucleophiles with various equivalents of the dielectrophilic synthon [C2]²⁺. In this study, intermediate N1-methylidenethiosemicarbazones (3a–b) were synthesized from 2-amino/allylsulfanyl-5-ethyl-1,3,4-thiadiazoles (1–b) via Vilsmeier–Haack formylation, followed by condensation with thiosemicarbazide in acetic acid.
Methods: Synthetic procedures were confirmed using NMR spectroscopy and elemental analysis. Pharmacological screening was performed to evaluate antitrypanosomal activity.
Results: The reaction of N1-methylidenethiosemicarbazones (3a–b) with α-halocarboxylic acids (monochloroacetic, 2-bromopropionic, 2-bromobutanoic) or α-bromo-γ-butyrolactone in acetic acid in the presence of sodium acetate yielded a series of 2-hydrazino-4-thiazolidinones containing the 6-phenylimidazo[2,1-b][1,3,4]thiadiazole moiety (4a–b) and their 5-alkyl-substituted derivatives (5a–d, 6a–b). Structures were confirmed by elemental analysis and NMR spectroscopy. All synthesized compounds (3a–b, 4a–b, 5a–d, 6a–b) were evaluated for in vitro antitrypanosomal activity against Trypanosoma brucei gambiense (Feo strain).
Conclusion: In vitro screening identified three highly active compounds—4b, 5b, and 5c—that exhibited significant trypanocidal activity with IC₅₀ values of 3.7–4.4 µM, comparable to the reference drug nifurtimox (IC₅₀ = 4.4 µM). These results highlight the potential of these 4-thiazolidinone derivatives as promising antitrypanosomal agents.
Methods: Synthetic procedures were confirmed using NMR spectroscopy and elemental analysis. Pharmacological screening was performed to evaluate antitrypanosomal activity.
Results: The reaction of N1-methylidenethiosemicarbazones (3a–b) with α-halocarboxylic acids (monochloroacetic, 2-bromopropionic, 2-bromobutanoic) or α-bromo-γ-butyrolactone in acetic acid in the presence of sodium acetate yielded a series of 2-hydrazino-4-thiazolidinones containing the 6-phenylimidazo[2,1-b][1,3,4]thiadiazole moiety (4a–b) and their 5-alkyl-substituted derivatives (5a–d, 6a–b). Structures were confirmed by elemental analysis and NMR spectroscopy. All synthesized compounds (3a–b, 4a–b, 5a–d, 6a–b) were evaluated for in vitro antitrypanosomal activity against Trypanosoma brucei gambiense (Feo strain).
Conclusion: In vitro screening identified three highly active compounds—4b, 5b, and 5c—that exhibited significant trypanocidal activity with IC₅₀ values of 3.7–4.4 µM, comparable to the reference drug nifurtimox (IC₅₀ = 4.4 µM). These results highlight the potential of these 4-thiazolidinone derivatives as promising antitrypanosomal agents.
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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