朝格尔碱衍生物的制备及其催化的4H-色烯并[2,3-b]吡啶-3-腈的合成  

Preparation and Application in the Synthesis of 4H-Chromeno-[2,3-b]pyridine-3-carbonitriles of Tröger's Base Derivatives

作　　者：陈雯 苑睿 房越 董宏瑞 布麦热叶木·亚生 苏柳娟 任璇璇 周杭 宛瑜 张鹏 周生亮 吴翚 Chen Wen;Yuan Rui;Fang Yue;Dong Hongrui;Yasen Bumaryam;Su Liujuan;Ren Xuanxuan;Zhou Hang;Wan Yu;Zhang Peng;Zhou Shengliang;Hui Wu(School of Chemistry and Materials Science,Jiangsu Normal University,Xuzhou,Jiangsu 221116;Key Laboratory of Biotechnology for Medicinal Plant of Jiangsu Province,Jiangsu Normal University,Xuzhou,Jiangsu 221116;School of Life Science,Jiangsu Normal University,Xuzhou,Jiangsu 221116)

机构地区：[1]江苏师范大学化学与材料科学学院,江苏徐州221116 [2]江苏师范大学江苏省药用植物生物技术重点实验室,江苏徐州221116 [3]江苏师范大学生命科学学院,江苏徐州221116

出　　处：《有机化学》2020年第4期988-996,共9页Chinese Journal of Organic Chemistry

基　　金：江苏省高校优势学科建设工程、江苏省高等学校自然科学研究(No.19KJB430019);徐州市科技计划项目(No.KC19242);江苏师范大学博士学位教师科研支持(No.17XLR023);江苏省研究生科研创新计划(Nos.KYCX18_2111,KYCX18_2116)资助项目.

摘　　要：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.A series of Schiff base catalysts(4)derived from Tr?ger?s base-NH2 were synthesized and used to promote the multi-component reactions of substituted salicylaldehydes,malononitrile and substituted 2-mercaptoimidazole to afford 5-(1Himidazol-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 1.549).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 Tr?ger?s bases in organocatalysis and showed the potential of products in new drug development.

关 键 词：朝格尔碱 有机催化 色烯[2 3-b]吡啶 生物活性 

分 类 号：TQ460.1[化学工程—制药化工] R914[医药卫生—药物化学]