N′-Substituted 4-Phenylpicolinohydrazonamides with Thiosemicarbazone Moiety as New Potential Antitubercular Agents: Synthesis, Structure and Evaluation of Antimicrobial Activity

Autor: Katarzyna Gobis, Małgorzata Szczesio, Andrzej Olczak, Ida Mazerant-Politowicz, Dagmara Ziembicka, Barbara Pacholczyk-Sienicka, Ewa Augustynowicz-Kopeć, Agnieszka Głogowska, Izabela Korona-Głowniak, Andrzej Fruziński
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Zdroj: Materials; Volume 15; Issue 16; Pages: 5513
ISSN: 1996-1944
DOI: 10.3390/ma15165513
Popis: Three new 4-phenylpicolin derivatives with a thiosemicarbazone structure were synthesized and evaluated for tuberculostatic activity. The compounds were obtained by the condensation of methyl 4-phenylpicolonimidate with the corresponding cycloalkylamino-1-carbothiohydrazides. The 1H NMR temperature spectra obtained showed proton lability at the nitrogen atom N2, and X-ray crystallography confirmed the zwitterionic structure of all products. ADME calculations indicate that the compounds can be tested as future drugs. All compounds were absorbed in the gastrointestinal tract. All compounds also showed very good tuberculostatic activity (MIC 3.1–12.5 µg/mL). Derivative 1b showed the best selectivity for M. tuberculosis compared to the other pathogenic species tested. The study has allowed the emergence of imine derivative 1b as a good structure for further optimization in the search for antitubercular drugs.
Databáze: OpenAIRE
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