Plant Biotechnology Persa

fa Synthesis and In Vitro Antitrypanosomal Evaluation of 2-Hydrazino-4-Thiazolidinones Containing 6-Phenylimidazo[2,1-b][1,3,4]thiadiazole Moiety Phytomedicine پژوهشي Research <div style="text-align: justify;">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. <img alt="" src="./files/site1/images/copuediting.png" style="width: 586px; height: 265px;" ></div> 2-Hydrazono-4-thiazolidinones, Imidazo[2,1-b][1,3,4]thiadiazoles, Heterocyclization Reaction, Spectral Data, Antitrypanosomal Activity 0 0 http://pbp.medilam.ac.ir/browse.php?a_code=A-10-25-81&slc_lang=fa&sid=1 Maryan Lelyukh lelyukh.m@gmail.com 10031947532846005861 10031947532846005861 Yes Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine Ihor Chaban ichaban@ymail.com 10031947532846005862 10031947532846005862 No Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine Roman Lysiuk pharmacognosy.org.ua@ukr.net 10031947532846005863 10031947532846005863 No Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine Arkadii Savchenko asavchenko@ymail.com 10031947532846005864 10031947532846005864 No Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine Nataliia Yelahina Yelahina@ymail.com 10031947532846005865 10031947532846005865 No Lugansk State Medical University, 16 Lypnya St. 36, Rivne 33017, Ukraine Daria Martyniuk Martyniuk@ymail.com 10031947532846005866 10031947532846005866 No Rivne Scientific Research Forensic Center of Ministry of Internal Affairs of Ukraine, V. Chervoniya, St. 39, Rivne, 33000, Ukraine Olexandra Komarytsya Komarytsya@ymail.com 10031947532846005867 10031947532846005867 No Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine Taras Chaban Chaban@ymail.com 10031947532846005868 10031947532846005868 No Danylo Halytsky Lviv National Medical University, Pekarska St. 69, Lviv 79010, Ukraine 2Lugansk State Medical University, 16 Lypnya St. 36, Rivne 33017, Ukraine