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New series of isoniazid hydrazones linked with electron-withdrawing substituents

Eva Vavříková, Slovenko Polanc, Marijan Kočevar, Janez Košmrlj, Kata Horváti, Szilvia Bősze, Jiřina Stolaříková, Aleš Imramovský, Jarmila Vinšová

. 2011 ; 46 (12) : 5902-5909. [pub] 20111013

Language English Country France

Document type Journal Article, Research Support, Non-U.S. Gov't

Persistent link   https://www.medvik.cz/link/bmc12022268

Grant support
NS10367 MZ0 CEP Register

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.

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