20.500.12556/RUL-166470 Spontaneous cyclization of 2-methylthiosemicarbazones yields new 1,2,4-triazolidine-3-thiones, useful as building blocks for drug design From the point of view of medicinal chemistry, thiosemicarbazones are interesting molecules as they exhibit various biological activities, such as antitumor, antifungal, antibacterial, antiviral, and antileukemic properties, and their synthesis is deeply investigated. However, the synthesis using 2-methylthiosemicarbazide as a starting compound to prepare new 1,2,4-triazolidine-3-thione compounds via 2-methylthiosemicarbazone cyclization has not been reported yet. Therefore, fifteen new 1,2,4-triazolidine-3-thione compounds were synthesized during a cyclization reaction using a simple green procedure with minimal use of hazardous solvents. The synthesized compounds were characterized with the techniques of NMR, IR, MS, and CHN elemental analysis. In addition, the structure of 11 of these compounds was confirmed by X-ray structure determination. Selected compounds were subjected to cytotoxicity assay and microbiological tests for antimicrobial susceptibility and quorum sensing inhibition and tested for their inhibitory effect on the metalloenzyme NDM-1, which causes antimicrobial resistance. 2-methylthiosemicarbazide 1 2 4-triazolidine-3-thiones cyclization green chemistry NDM-1 2-metiltiosemikarbazid 1 2 4-triazolidin-3-tioni ciklizacija zelena kemija NDM-1 true false true Angleški jezik Slovenski jezik Članek v reviji 2025-01-14 09:00:20 2025-01-14 09:00:22 2025-01-15 03:54:36 0000-00-00 00:00:00 2025 0 0 10 str. iss. 2, art. e202404001 Vol. 10 15 Jan. 2025 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.288.3:66.095.25 2365-6549 10.1002/slct.202404001 222062339 ChemistrySelect_-_2025_-_Gricar_-_Spontaneous_Cyclization_of_2‐Methylthiosemicarbazones_Yields_New_1_2.pdf ChemistrySelect_-_2025_-_Gricar_-_Spontaneous_Cyclization_of_2‐Methylthiosemicarbazones_Yields_New_1_2.pdf 1 F0D9216D33C715AB4E352A28691ACE0D a6a4638731b5d589d05bd183447e13eb2ce16b7ee4845e6180616279ebb42ed8 2e741498-d24d-11ef-b232-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=198116 https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/slct.202404001 1 dc37313e-d24c-11ef-b232-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=198110 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0