Novel salicylanilides from 4,5-dihalogenated salicylic acids: Synthesis, antimicrobial activity and cytotoxicity
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
28126437
DOI
10.1016/j.bmc.2017.01.016
PII: S0968-0896(16)30882-3
Knihovny.cz E-resources
- Keywords
- Cytotoxicity, Double halogenation, In vitro antimycobacterial activity, Salicylanilides, Tuberculosis,
- MeSH
- Antitubercular Agents chemical synthesis chemistry pharmacology MeSH
- Hep G2 Cells MeSH
- Humans MeSH
- Microbial Sensitivity Tests MeSH
- Molecular Structure MeSH
- Tuberculosis, Multidrug-Resistant drug therapy MeSH
- Mycobacterium drug effects growth & development MeSH
- Salicylanilides chemical synthesis chemistry pharmacology MeSH
- Salicylates chemistry pharmacology MeSH
- Cell Survival drug effects MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Antitubercular Agents MeSH
- salicylanilide MeSH Browser
- Salicylanilides MeSH
- Salicylates MeSH
Salicylanilides have proved their activity against tuberculosis (TB). One weak electron-withdrawing substituent is favored at the salicylic part, specially Cl or Br atoms at positions 4 or 5. On the other hand, the antimycobacterial activity of salicylanilides is negatively affected when a strong electron-withdrawing substituent (NO2) is present at the same positions. Herein we describe the synthesis and characterization of novel salicylanilides possessing two weak electron-withdrawing groups (halogen atoms) at their salicylic part and compare their antitubercular activity with their monohalogenated analogues. All dihalogenated derivatives proved to possess antitubercular activity at a very narrow micromolar range (MIC=1-4μM), similar with their most active monohalogenated analogues. More importantly, the most active final molecules were further screened against multidrug resistant strains and found to inhibit their growth at the range of 0.5-4μM.
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