Synthesis of Levoglucosenone‐derived Thiosemicarbazones as Promising Antituberculosis Agents

• Published in: ChemistrySelect (Weinheim) 2023-11, Vol.8 (43), p.n/a
• Main Authors: Tsai, Yi‐hsuan, Aira, Nicolás, Ensinck, Delfina, Banchio, Claudia, Gramajo, Hugo, Suárez, Alejandra G., Spanevello, Rolando A., Sarotti, Ariel M.
• Format: Article
• Language: English
• Subjects: antimycobacterial; H37Ra; levoglucosenone; thiosemicarbazone; tuberculosis
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202303776

A series of levoglucosenone‐derived thiosemicarbazones have been designed and synthesized following a simple and straightforward procedure. The in vitro antimycobacterial activity of the full library were evaluated against M. tuberculosis H37Ra, with 4 compounds being active in the 1.9–10.7 μg/mL concentration range. To determine the influence of the thiosemicarbazone fragment, the synthetic precursors were analyzed, as well as 50 structurally diverse triazoles and isoxazoles derived from levoglucosenone. Comparing the observed activities with the levels of cell viability in L929 cells at the MIC, it can be concluded that the derivatives reported in this work represent interesting candidates for further development of promising antituberculosis agents. Going green. During our journey towards the discovery of bioactive compounds from levoglucosenone, a biomass‐derived enone, new thiosemicarbazones have been designed and synthesized following a simple and straightforward procedure. The in vitro antimycobacterial activity of the full library were evaluated against M. tuberculosis H37Ra, with 4 compounds being active in the 1.9–10.7 μg/mL concentration range.