一些N-取代硝基咪唑衍生物作为潜在抗氧化剂和抗真菌剂的合成

Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents.

作者信息

Olender Dorota, Zwawiak Justyna, Lukianchuk Victor, Lesyk Roman, Kropacz Aleksandra, Fojutowski Andrzej, Zaprutko Lucjusz

机构信息

Department of Organic Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland.

出版信息

Eur J Med Chem. 2009 Feb;44(2):645-52. doi: 10.1016/j.ejmech.2008.05.016. Epub 2008 May 28.

DOI:10.1016/j.ejmech.2008.05.016

PMID:18590938

Abstract

Some new nitroimidazole derivatives have been synthesized by treating 4,5-dinitro- and 2-methyl-4,5-dinitroimidazoles with epoxypropane, epichlorohydrin or phenacyl bromide in alkylation reactions. The nitro group in N-substituted 4,5-dinitro- and 2-methyl-4,5-dinitroimidazoles has been replaced with primary and secondary amines to afford 4-amino-5-nitroimidazole derivatives. Some of the compounds have been tested for their antioxidant and antifungal properties against fungi species acting on timber. Nearly all of them have shown significant antioxidant activity in comparison with that of tocopherol, which is used as a reference substance. Two compounds from those tested have revealed very strong fungistatic activity against Sclerophoma pityophila.

摘要

通过在烷基化反应中用环氧丙烷、环氧氯丙烷或溴代苯乙酮处理4,5-二硝基咪唑和2-甲基-4,5-二硝基咪唑，合成了一些新的硝基咪唑衍生物。N-取代的4,5-二硝基咪唑和2-甲基-4,5-二硝基咪唑中的硝基已被伯胺和仲胺取代，得到4-氨基-5-硝基咪唑衍生物。对其中一些化合物针对作用于木材的真菌物种的抗氧化和抗真菌性能进行了测试。与用作参考物质的生育酚相比，几乎所有化合物都显示出显著的抗氧化活性。所测试的化合物中有两种对嗜皮菌显示出非常强的抑菌活性。