摘要/Abstract

由朝格尔碱-氨基合成了一系列席夫碱（4），将其作为高效催化剂催化了取代水杨醛、丙二腈和取代2-巯基咪唑的多组分反应，得到一系列5-（1H-咪唑-2-硫代）-2，4-二氨基-5H-色烯并[2，3-b]吡啶-3-腈衍生物（8）.通过¹H NMR初步探讨了催化机理.生物活性结果表明：大多数产品对人乳腺癌细胞（MCF-7）和腺癌人肺泡基底上皮细胞（A549）表现出高度抑制作用.5-（1H-咪唑-2-基硫基）-2，4-二氨基-7-氟-5H-苯并[2，3-b]吡啶-3-腈（8s）对金黄色葡萄球菌（野生型）和大肠杆菌（野生型）具有抗菌活性.这些结果扩展了朝格尔碱衍生物在有机催化中的应用，显示产品在新药开发领域具有潜力.
关键词: 朝格尔碱, 有机催化, 色烯[2,3-b]吡啶, 生物活性
A series of Schiff base catalysts (4) derived from Tröger's base-NH₂ were synthesized and used to promote the multi-component reactions of substituted salicylaldehydes, malononitrile and substituted 2-mercaptoimidazole to afford 5-(1H-imidazol-2-ylthio)-2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile derivatives (8) efficiently. The reaction mechanism was discussed based on the ¹H NMR analysis preliminarily. Most of products showed high inhibitory on the human breast adenocarcinoma cell (MCF-7) and adenocarcinomic human alveolarbasal epithelial cell (A549). 5-(1H-Imidazol-2-ylthio)-2,4-diamino-7-fluoro-5H-chromeno[2,3-b]pyridine-3-carbonitrile has antibacterial activity against Staphylococcus aureus (wild type) and Escherichia coli (wild type). The results expanded the application of Tröger's bases in organocatalysis and showed the potential of products in new drug development.
Key words: Tröger's base, organoatalysis, chromeno[2,3-b]pyridine, biological activity


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