New series of isoniazid hydrazones linked with electron-withdrawing substituents

被引:36
|
作者
Vavrikova, Eva [1 ]
Polanc, Slovenko [2 ]
Kocevar, Marijan [2 ]
Kosmrlj, Janez [2 ]
Horvati, Kata [3 ]
Bosze, Szilvia [3 ]
Stolarikova, Jirina [4 ]
Imramovsky, Ales [5 ]
Vinsova, Jarmila [1 ]
机构
[1] Charles Univ Prague, Fac Pharm, Dept Inorgan & Organ Chem, Hradec Kralove 50005, Czech Republic
[2] Univ Ljubljana, Fac Chem & Chem Technol, SI-1000 Ljubljana, Slovenia
[3] Eotvos Lorand Univ, Res Grp Peptide Chem, Hungarian Acad Sci, H-1117 Budapest, Hungary
[4] Ctr Hyg Labs, Inst Publ Hlth, Ostrava 70200, Czech Republic
[5] Univ Pardubice, Fac Chem Technol, Pardubice 53210, Czech Republic
关键词
Tuberculosis; Isoniazid; Hydrazone; Antitubercular drug; In vitro activity; RAPID COLORIMETRIC ASSAY; MYCOBACTERIUM-TUBERCULOSIS; DERIVATIVES; SURVIVAL; GROWTH;
D O I
10.1016/j.ejmech.2011.09.054
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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 mu mol L-1) as isoniazid (INH), better activity against Mycobacterium kansasii 325/80 (MIC 0.125-0.250 mu mol L-1), high value of selectivity index (SI) and IC50 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. (C) 2011 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:5902 / 5909
页数:8
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