有机化学 ›› 2014, Vol. 34 ›› Issue (3): 515-521.DOI: 10.6023/cjoc201310010 上一篇    下一篇

研究论文

1,3-二羟基呫吨酮类化合物的简洁合成及清除亚硝酸根作用研究

毛双双a, 郑欢欢a, 罗翠婷a, 陈河如a,b,c   

  1. a 暨南大学药学院中药及天然药物研究所 广州 510632;
    b 中国科学院上海药物研究所新药研究国家重点实验室 上海 201203;
    c 广东省中药药效物质基础及创新药物研究重点实验室 广州 510632
  • 收稿日期:2013-10-11 修回日期:2013-11-10 出版日期:2014-03-25 发布日期:2013-11-21
  • 通讯作者: 陈河如 E-mail:thrchen@jnu.edu.cn
  • 基金资助:

    国家自然科学基金(No. 81172982);广东省科技计划社会发展重点(No. 2010A030100006);新药研究国家重点实验室开放基金(No. SIMM1302KF-12)资助项目.

Concise Syntheses of 1,3-Dihydroxylxanthones and Their Clearance Effections against Nitrite

Mao Shuangshuanga, Zheng Huanhuana, Luo Cuitinga, Chen Herua,b,c   

  1. a Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632;
    b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
    c Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632
  • Received:2013-10-11 Revised:2013-11-10 Online:2014-03-25 Published:2013-11-21
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 81172982), the Guangdong Provincial Project of Science and Technology (No. 2010A030100006) and the State Key Laboratory of Drug Research (No. SIMM1302KF-12).

以间苯三酚为起始原料,在伊顿试剂的催化作用下,与不同取代水杨酸反应合成1,3-二羟基呫吨酮类化合物3a3l 12个,收率63%~87%,并探讨了反应机理及结构-反应活性关系. 利用紫外分光光度法测定了所合成化合物对亚硝酸盐的清除作用,结果表明,在37 ℃、 pH 3及反应时间为30 min条件下,1,3-呫吨酮类化合物对亚硝酸根均有较好的清除作用,其中化合物3f3b的清除作用最强,清除率达34%. 同时对1,3-二羟基呫吨酮类化合物清除亚硝酸盐的作用机制及构效关系进行了探讨.

关键词: 呫吨酮, 有机合成, 亚硝酸盐, 癌症防治, 伊顿试剂

Twelve 1,3-dihydroxylxanthones (3a3l) were synthesized under the catalysis of Eaton's reagent applying phloroglucinol and substituted salicylic acids as starting materials. The yields were from 63% to 87%. The reaction mechanism and their structure-reaction activity relationship have been discussed. The clearance effections of all the prepared xanthones against nitrite have been investigated by UV spectrophotometry. It is disclosed that all the tested xanthones have obvious clearance effections against nitrite at the conditions of pH 3, room temperature, and 30 min treatment. 3b and 3f are identified as the most active compounds with clearance rate up to 34.0%. The clearance mechanism of xanthones against nitrite and their structure-activity relationships were also included here.

Key words: xanthones, organic synthesis, nitrite, cancer prevention, Eaton’s reagent