高等学校化学学报 ›› 2013, Vol. 34 ›› Issue (11): 2531.doi: 10.7503/cjcu20130185

• 有机化学 • 上一篇    下一篇

3-芳基苯并呋喃酮类化合物的合成及抗肿瘤活性

吕泽良1,2,3, 高扬4, 李军4, 黄桐堃1, 何树杰1, 邹永1   

  1. 1. 中国科学院广州化学研究所, 广州 510650;
    2. 中国科学院大学, 北京 100049;
    3. 曲靖师范学院化学化工学院, 曲靖 655011;
    4. 浙江大学医学院附属第二医院, 杭州 313000
  • 收稿日期:2013-03-01 出版日期:2013-11-10 发布日期:2013-04-08
  • 作者简介:邹永,男,博士,研究员,博士生导师,主要从事药物合成研究,E-mail:zou_jinan@163.com
  • 基金资助:

    国家自然科学基金(批准号:21272280)、广东省中国科学院全面战略合作项目(批准号:2009B091300125)、广东省战略新兴产业核心技术攻关项目(批准号:2011A081401002)、"十二五"国家重大新药创制项目(批准号:2011ZX09202-101-07)和广州市科技计划项目(批准号:2012J4300097)资助.

Synthesis and Antitumor Activities of 3-Arylbenzofunanone Analogues

LV Ze-Liang1,2,3, GAO Yang4, LI Jun4, HUANG Tong-Kun1, HE Shu-Jie1, ZOU Yong1   

  1. 1. Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, China;
    2. University of Chinese Academy of Sciences, Beijing 100049, China;
    3. College of Chemistry and Chemical Engineering, Qujing Normal University, Qujing 655011, China;
    4. The Second Afflilated Hospital, School of Medicine, Zhejiang University, Hangzhou 313000, China
  • Received:2013-03-01 Online:2013-11-10 Published:2013-04-08

摘要:

以甲氧基取代苯甲醛和氯仿为起始物, 以四丁基溴化铵(TBAB)为催化剂, 在氢氧化钠溶液中反应制得甲氧基取代扁桃酸钠, 经酸化得到相应的甲氧基取代扁桃酸; 在三氟化硼-乙醚催化下, 甲氧基取代扁桃酸分别与不同的酚类化合物发生串联的酯化-分子内环合反应, 便捷、 高效地合成了13种3-芳基苯并呋喃酮类化合物. 采用噻唑蓝(MTT)法对其中11种化合物进行了肿瘤细胞增殖抑制活性研究, 结果表明化合物4a, 4j及4a, 4i具有较强的抗肿瘤活性.

关键词: 3-芳基苯并呋喃酮, 甲氧基取代扁桃酸, 酚类, 抗肿瘤活性

Abstract:

Starting from methoxyl-substituted benzaldehydes and chloroform, a series of methoxyl-substituted mandelic sodium salts were synthesized in the presence of sodium hydroxide and catalytic amount of tetrabuty-lammonium bromide(TBAB), the corresponding methoxyl-substituted mandelic acids could readily be obtained by acidification. These intermediates on reaction with various substituted phenols in the presence of boron trifluoride etherate via a sequential esterification-alkylation process to give 13 3-arylbenzofunanone analogues in high yields with simple procedures. The inhibitory effects of 11 compounds on cell proliferation were investigated by methylthiazolyldiphenyl-tetrazolium bromide(MTT) method using SW620, A549 and MNNG/HOS cell lines. The results showed that the 3-arylbenzofunanone analogues 4a, 4j and 4a, 4i exhibited some activities against the proliferation of the cell lines.

Key words: 3-Arylbenzofunanone, Methoxyl-substituted mandelic acid, Phenol, Antitumor activity

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