2-取代卤代苯并咪唑的合成及其抗分枝杆菌活性

Synthesis and antimycobacterial activity of 2-substituted halogenobenzimidazoles.

作者信息

Kazimierczuk Z, Andrzejewska M, Kaustova J, Klimesova V

机构信息

Institute of Chemistry, Agricultural University, 159C Nowoursynowska Street, 02-787 Warsaw, Poland.

出版信息

Eur J Med Chem. 2005 Feb;40(2):203-8. doi: 10.1016/j.ejmech.2004.10.004.

DOI:10.1016/j.ejmech.2004.10.004

PMID:15694655

Abstract

A series of substituted 2-polyfluoroalkyl and 2-nitrobenzylsulphanyl benzimidazoles was synthesized. The compounds were evaluated for their activity against four Mycobacterium strains; the activities were expressed as the minimum inhibitory concentration (MIC). The substances tested showed appreciable antimycobacterial activity, particularly 5,6-dichloro-2-nonafluorobutylbenzimidazole (2h), and 5-halogeno- (5a-c) and 4,6-dihalogeno- (5d and 5g) 2-(3,5-dinitrobenzylsulphanyl)benzimidazoles, whose MIC values for Mycobacterium kansasii and Mycobacterium avium exceeded that of isoniazide that was used as a reference compound. Relationships between structure and biological activity of the tested benzimidazole derivatives are discussed.

摘要

合成了一系列取代的2-多氟烷基和2-硝基苄硫基苯并咪唑。评估了这些化合物对四种分枝杆菌菌株的活性；活性以最低抑菌浓度（MIC）表示。测试的物质显示出明显的抗分枝杆菌活性，特别是5,6-二氯-2-九氟丁基苯并咪唑（2h），以及5-卤代-（5a - c）和4,6-二卤代-（5d和5g）2-（3,5-二硝基苄硫基）苯并咪唑，它们对堪萨斯分枝杆菌和鸟分枝杆菌的MIC值超过了用作参考化合物的异烟肼。讨论了测试的苯并咪唑衍生物的结构与生物活性之间的关系。