Synthesis and in vitro antimycobacterial and isocitrate lyase inhibition properties of novel 2-methoxy-2'-hydroxybenzanilides, their thioxo analogues and benzoxazoles
Language English Country France Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
22960697
DOI
10.1016/j.ejmech.2012.08.016
PII: S0223-5234(12)00495-3
Knihovny.cz E-resources
- MeSH
- Anilides chemical synthesis chemistry pharmacology MeSH
- Benzoxazoles chemical synthesis chemistry pharmacology MeSH
- Hep G2 Cells MeSH
- Enzyme Inhibitors chemical synthesis chemistry pharmacology MeSH
- Isocitrate Lyase antagonists & inhibitors metabolism MeSH
- Humans MeSH
- Microbial Sensitivity Tests MeSH
- Molecular Structure MeSH
- Mycobacterium drug effects MeSH
- Antineoplastic Agents chemical synthesis chemistry pharmacology MeSH
- Drug Screening Assays, Antitumor 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
- 2-methoxy-2'-hydroxybenzanilide MeSH Browser
- Anilides MeSH
- Benzoxazoles MeSH
- Enzyme Inhibitors MeSH
- Isocitrate Lyase MeSH
- Antineoplastic Agents MeSH
A new series of 2-methoxy-2'-hydroxybenzanilide derivatives and their thioxo analogues have been synthesised and characterised by IR, NMR and elemental analysis. These compounds were investigated for their in vitro antimycobacterial activities against Mycobacterium tuberculosis 331/88, Mycobacterium avium 330/88, Mycobacterium kansasii 235/80, clinically isolated M. kansasii 6509/96 and the ability to act as in vitro isocitrate lyase inhibitors. The best ICL inhibitors were two compounds from the thiobenzanilide group (8f, 8m), which exhibited an inhibition potential that was equal to the standard compound, 3-nitropropionic acid. In addition, the best antimycobacterial properties were exhibited by benzanilide derivatives 6h, 6k and 6l with 5-Cl and 4' or 5' Cl/Br substitution. For all the thiobenzanilide derivatives tested, two conformers were observed in the NMR spectra, which is most likely due to the hindered rotation of the C-N bond.
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