Syntheses of biologically active ubiquinone derivatives.
Syntheses of biologically active ubiquinone derivatives.
复制标题
具有生物活性的泛醌衍生物的合成。
作者：
Yu,CA;Yu,L
C.- A. Yu* 和L.俞摘要：通过烷酰基或卤代烷酰基过氧化物与泛醌0的自由基偶联反应，合成了6-烷基泛醌或6-（叔卤代烷基）泛醌衍生物。后者由2-甲氧基-4-甲基苯酚经硝化、甲基化、还原、氧化等反应合成。6-（α-卤代烷基）泛醌通过汞辅助溶剂分解技术转化为6-（α-羟烷基）泛醌。然后将6-（（N-羟基烷基）泛醌用羧酸酐或带有报告基团的羧酸酯化，所述报告基团例如光亲和标记物N-（4-叠氮基-2-硝基-苯基）-，S-丙氨酸，或自旋标记物3-羧基-2，2，5，5-四甲基-3-吡咯啉基-1-氧基。以二环己基碳二亚胺和吡啶为催化剂，用3%乙醇-苯为展开剂，制备硅胶薄层色谱法对酯化产物进行纯化。光谱特性
C.-A. Yu* and L. Yu abstract: Various 6-alkylubiquinone or 6-(tv-haloalkyl)-ubiquinone derivatives were synthesized through a radical coupling reaction between alkanoyl or-haloalkanoyl peroxides and ubiquinone 0. The latter was synthesized from 2-methoxy-4-methylphenol via nitration, methylation, reduction, and oxidation by modifications of the reported methods. 6-(-Haloalkyl) ubiquinones were converted to 6-(a>-hydroxyalkyl) ubiquinones by a mercuric-assisted solvolysis technique. The 6-((v-hydroxyalkyl) ubiquinones were then esterified with carboxylic acid anhydrides or carboxylic acid bearing reporting groups, such as a photoaffinity label, JV-(4-azido-2-nitro-phenyl)-, S-alanine, or a spin-label, 3-carboxy-2, 2, 5, 5-tetramethyl-3-pyrrolinyl-1-oxy. Theesterification was catalyzed by dicyclohexylcarbodiimide and pyridine, and the esters were purified by preparative silica gel thin-layer chromatography, developed by 3% ethanolin benzene. The spectral properties