Novel derivatives of nitro-substituted salicylic acids: Synthesis, antimicrobial activity and cytotoxicity

Georgios Paraskevopoulos, Martin Krátký, Jana Mandíková, František Trejtnar, Jiřina Stolaříková, Petr Pávek, Gurdyal Besra, Jarmila Vinšová

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)
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Abstract

Inspired by the high antituberculous activity of novel nitro-substituted derivatives and based on promising predicted ADMET properties we have synthesized a series of 33 salicylanilides containing nitro-group in their salicylic part and evaluated them for their in vitro antimycobacterial, antimicrobial and antifungal activities. The presence of nitro-group in position 4 of the salicylic acid was found to be beneficial and the resulting molecules exhibited minimum inhibitory concentrations (MICs) ranging from 2 to 32μM against Mycobacterium tuberculosis. The best activity was found for 2-hydroxy-4-nitro-N-[4-(trifluoromethyl)phenyl]benzamide (MIC=2μM). 4-Nitrosalicylanilides were also found to be active against all Staphylococcus species tested while for MRSA strain 2-hydroxy-4-nitro-N-[4-(trifluoromethyl)phenyl]benzamide's MIC was 0.98μM. None of the nitrosalicylanilides was active against Enterococcus sp. J 14365/08 and no considerable activity was found against Gram-negative bacteria or fungi. The hepatotoxicity of all nitrosalicylanilides was found to be in the range of their MICs for HepG2 cells.

Original languageEnglish
Pages (from-to)7292-301
Number of pages10
JournalBioorganic & Medicinal Chemistry
Volume23
Issue number22
Early online date24 Oct 2015
DOIs
Publication statusPublished - 15 Nov 2015

Keywords

  • Salicylanilides
  • Nitro group
  • In silico ADMET prediction
  • In vitro antimycobacterial activity
  • Cytotoxicity

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