New fluorine-containing hydrazones active against MDR-tuberculosis

Eva Vavříková, Slovenko Polanc, Marijan Kočevar, Kata Horváti, Szilvia Bsze, Jiřina Stolaříková, Kateřina Vávrová, Jarmila Vinšová

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Several new fluorine-containing hydrazones were synthesized and screened for their in vitro antimycobacterial activity. Nine of these derivatives have shown a remarkable activity against MDR-TB strain with MIC 0.5 μg/mL and high value of selectivity index (SI). Compound 3h with the highest SI (1268.58) was used for stability evaluation with putative metabolites (ciprofloxacin and formylciprofloxacin) detection. Compound 3h was stable at pH 7.4 of aqueous buffer and rat plasma, in acidic buffers (at pH 3 and 5) slow decomposition was observed. Interestingly, no formylciprofloxacin was detected in the solution, and only slightly increased concentration of ciprofloxacin was observed instead. Trifluoromethyl hydrazones 3f and 3g exhibited the best activity also against two strains of Mycobacterium kansasii (MIC 1-4 μmol/L). All evaluated compounds were found to be non-cytotoxic.

Original languageEnglish
Pages (from-to)4937-4945
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Volume46
Issue number10
DOIs
Publication statusPublished - Oct 1 2011

Keywords

  • Antitubercular drug
  • Hydrazone
  • In vitro activity
  • Multidrug-resistant tuberculosis
  • Tuberculosis

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Vavříková, E., Polanc, S., Kočevar, M., Horváti, K., Bsze, S., Stolaříková, J., Vávrová, K., & Vinšová, J. (2011). New fluorine-containing hydrazones active against MDR-tuberculosis. European Journal of Medicinal Chemistry, 46(10), 4937-4945. https://doi.org/10.1016/j.ejmech.2011.07.052