New series of isoniazid hydrazones linked with electron-withdrawing substituents
Language English Country France Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
22018878
DOI
10.1016/j.ejmech.2011.09.054
PII: S0223-5234(11)00715-X
Knihovny.cz E-resources
- MeSH
- Anti-Bacterial Agents chemistry pharmacology MeSH
- Antitubercular Agents chemistry pharmacology MeSH
- Mycobacterium Infections, Nontuberculous drug therapy MeSH
- Hep G2 Cells MeSH
- Hydrazones chemistry pharmacology MeSH
- Mycobacterium avium-intracellulare Infection drug therapy MeSH
- Isoniazid chemistry pharmacology MeSH
- Humans MeSH
- Microbial Sensitivity Tests MeSH
- Mycobacterium avium Complex drug effects MeSH
- Mycobacterium kansasii drug effects MeSH
- Mycobacterium tuberculosis drug effects MeSH
- Tuberculosis drug therapy MeSH
- Cell Survival drug effects MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Anti-Bacterial Agents MeSH
- Antitubercular Agents MeSH
- Hydrazones MeSH
- Isoniazid MeSH
A series of new isoniazid hydrazones was synthesized by two procedures. In the first isoniazid was activated with diethoxymethyl acetate and condensed with the appropriate anilines. Alternatively, substituted anilines were activated by diethoxymethyl acetate and subsequently condensed with isoniazid. NMR study confirmed that both synthetic approaches gave the same tautomer. All compounds were screened for in vitro antimycobacterial activity. Most of them exhibited the same activity against Mycobacterium tuberculosis (MIC 1 μmol L(-1)) as isoniazid (INH), better activity against Mycobacterium kansasii 325/80 (MIC 0.125-0.250 μmol L(-1)), high value of selectivity index (SI) and IC(50) between 0.0218 and 0.326 mmol L(-1). Compound 2o with the best SI was used as a model compound for the stability test and was found to be stable at neutral pH, but under acidic conditions it slowly hydrolysed.
References provided by Crossref.org
N-substituted 2-isonicotinoylhydrazinecarboxamides--new antimycobacterial active molecules
