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有机化学
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有机化学 ›› 2015, Vol. 35 ›› Issue (7): 1537-1543.DOI: 10.6023/cjoc201502003 上一篇    下一篇

研究简报

苯并二氢呋喃新木脂素Mannich碱衍生物的合成及生物活性研究

史玲, 王彩芳, 徐雨, 汪秋安   

  1. 湖南大学化学化工学院 长沙 410082
  • 收稿日期:2015-02-03 修回日期:2015-03-09 发布日期:2015-03-17
  • 通讯作者: 汪秋安 E-mail:WangQA@hnu.edu.cn
  • 基金资助:

    国家“十二五”科技支撑计划(No. 2012BAD31B02)和湖南省自然科学基金(No. 14JJ2048)资助项目.

Synthesis and Biological Activity of BenzodihydrofuranNeolignans and Their Mannich Base Derivatives

Shi Ling, Wang Caifang, Xu Yu, Wang Qiu'an   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2015-02-03 Revised:2015-03-09 Published:2015-03-17
  • Supported by:

    Project supported by the National“Twelfth Five-Year”Plan for Science & Technology Support (No. 2012BAD31B02) and the Hunan Provincial Natural Science Foundation of China (No. 14JJ2048).

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以异丁香酚为原料, 经氧化银催化的自由基仿生氧化偶联反应, 一步合成了天然苯并二氢呋喃新木脂素licarin A (1), 然后经2,3-二氯-5,6-二氰基对苯醌(DDQ)氧化脱氢反应得到另一苯并二氢呋喃新木脂素化合物2-(3'-甲氧基-4'-羟基)苯基-3-甲基-5-甲酰乙烯基-7-甲氧基-2,3-苯并二氢呋喃(2). 以苯并二氢呋喃新木脂素1和2为底物, 以甲醇为溶剂, 分别与甲醛、二级胺在酸性介质中发生微波协助的Mannich反应, 合成了11个新的苯并二氢呋喃新木脂素Mannich碱衍生物3～13. 所合成的化合物通过1HNMR、13CNMR和MS等进行了结构确证, 并采用CCK-8法测试了所合成化合物对人宫颈癌Hela细胞株的体外抑制活性. 结果表明大部分化合物对Hela细胞增殖具有良好的抑制作用, 其中化合物2 (IC50 0.438 μmol/L)和化合物9 (IC50 8.358 μmol/L)具有最强的Hela细胞增殖抑制活性.

关键词: 苯并二氢呋喃新木脂素, licarin A, Mannich 碱衍生物, 合成, 生物活性

The natural benzodihydrofuran neolignans licarin A (1) was synthesized from isoeugenol through biomimetic oxidative coupling. Then licarin A (1) was transformed into another benzodihydrofuran compound 2-(3'-methoxy-4'-hydroxy)- phenyl-3-methyl-5-formylvinyl-7-methoxy-2,3-benzodihydrofuran (2) through 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidative reaction. Based on Mannich reaction of 1 or 2 with viarious secondary amines and formaldehyde in acidic alcohol system under microwave-assistanced, eleven new benzodihydrofuran neolignan Mannich base derivatives 3～13 were synthesized. All the synthetic compounds were tested for antiproliferation activity against human cervical carcinoma Hela cells by the standard CCK-8 method. The results showed that most of the target compounds exhibited moderate to potent antiproliferation activity against Heala cells. Among them, compound 2 (IC50 0.438 μmol/L) and compound 9 (IC50 8.358 μmol/L) displayed the strongest antiproliferation activity against Hela cells.

Key words: benzodihydrofuran, licarin A, Mannich base derivatives, synthesis, biological activity