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2012 , Vol. 32 >Issue 11: 2141 - 2147

DOI: https://doi.org/10.6023/cjoc201204001

研究论文

查尔酮及其螺杂环衍生物的合成、晶体结构、抗氧化活性研究

  • 吴建章 ,
  • 李物兰 ,
  • 陈玲姿 ,
  • 楚生辉 ,
  • 赵承光 ,
  • 卫涛 ,
  • 杨树林 ,
  • 李校堃
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  • a 南京理工大学生物工程研究所 南京 210094;
    b 温州医学院药学院 温州 325035;
    c 温州医学院信息与工程学院 温州 325035

收稿日期: 2012-04-01

  修回日期: 2012-06-18

  网络出版日期: 2012-07-02

基金资助

浙江省医药卫生科技计划(No. 2012KYA129)、温州市科技局(No. Y20090101)、浙江省中医药科技计划B类(No. 2012ZB102)资助项目.

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Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues

  • Wu Jianzhang ,
  • Li Wulan ,
  • Chen Lingzi ,
  • Chu Shenghui ,
  • Zhao Chenguang ,
  • Wei Tao ,
  • Yang Shulin ,
  • Li Xiaokun
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  • a Institute of Biotechnology, Nanjing University of Science and Technology, Nanjing 210094;
    b School of Pharmacy, Wenzhou Medical College, Wenzhou 325035;
    c College of Information Science and Computer Engineering, Wenzhou Medical College, Wenzhou 325035

Received date: 2012-04-01

  Revised date: 2012-06-18

  Online published: 2012-07-02

Supported by

Project supported by the Technology Foundation for Medical Science of Zhejiang Province (No. 2012KYA129), the Project of Wenzhou Sci & Tech Bureau (No. 20090101), and the Technology Foundation for Chinese Medicine of Zhejiang Province (No. 2012ZB102).

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摘要

为了合成新结构类型查尔酮衍生物, 发现具有抗氧化活性的查尔酮类化合物, 设计合成了查尔酮A和螺杂环B两种类型, 共21个查尔酮类似物, 结构经ESI-MS, ESI-HRMS和1H NMR确认. 培养出螺杂环B1的单晶, 通过X衍射确证了其为单斜晶系. 其中螺杂环B为新结构类型化合物, 通过1,3-偶极环加成反应, 用不需加催化剂的“一锅煮”方法合成, 该反应具有很好的立体选择性和区域选择性、且环境友好. 用DPPH法测试了所有化合物的抗氧化活性, 筛选出了多个对1,1-二苯基-2-三硝基苯肼(DPPH)自由基具有良好清除率的化合物, a环3,4-OH取代的两类化合物都具有良好的抗氧化活性, 苯环邻位二羟基取代的查尔酮类化合物可能具有很好的抗氧化活性.

关键词： 查尔酮; 螺杂环; 合成; DPPH; 抗氧化活性; 晶体结构

本文引用格式

吴建章 , 李物兰 , 陈玲姿 , 楚生辉 , 赵承光 , 卫涛 , 杨树林 , 李校堃 . 查尔酮及其螺杂环衍生物的合成、晶体结构、抗氧化活性研究[J]. 有机化学, 2012 , 32(11) : 2141 -2147 . DOI: 10.6023/cjoc201204001

Abstract

To synthesize new structure type chalcone analogues, and obtain chalcone analogues with good antioxidant activity. Two types of chalcone analogs, chalcones A and spiro-heterocyclic B were designed and synthesized, and the structures of 21 compounds were characterized by 1H NMR, ESI-MS and ESI-HRMS. Single-crystal of spiro-heterocyclic B was cultured, and its single-crystal structure was determined by X-ray diffraction study. The crystal structure of B1 was monoclinic system, space group C2/c, with cell dimensions of a＝21.350(3) Å, b＝8.6256(10) Å, c＝26.161(3) Å. Spiro-heterocyclic B is the new structure type, and obtained by one-pot synthesis which is 1,3-dipolar cycloaddition reaction and no catalyst. The synthesis of spiro-heterocyclic B is not only high regioselectivity and stereoselectivity, but also environmentally friendly. The antioxidant activities in vitro were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Many compounds, which can have strong activity of scavenging DPPH free radicals, were screened. In the 2 types of chalcones analogs, the compounds with 3,4-(OH)2 in “a” ring have excellent antioxidant activities. The chalcone analogs with o-dihydroxy in benzene ring maybe have good antioxidant activities.

Key words： chalcones; spiro-heterocyclic; synthesis; DPPH; antioxidant activities; crystal structure

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