应用化学 ›› 2010, Vol. 27 ›› Issue (06): 658-663.DOI: 10.3724/SP.J.1095.2010.90532

• 研究论文 • 上一篇    下一篇

微波辐照2,6-二(2’-咪唑啉-2’-基)吡啶的合成及其与DNA的相互作用

张金艳1,肖小明1*,谭年元2,徐莎莎1,欧阳泽英1   

  1. (1.湖南师范大学化学化工学院 长沙 410081;2.湖南工程学院化学化工学院 湘潭)
  • 收稿日期:2009-08-13 修回日期:2009-10-19 出版日期:2010-06-10 发布日期:2010-06-10
  • 通讯作者: 肖小明,男,硕士,教授; E-mail:xmxiao@hunnu.edu.cn; 研究方向:配位化学及电化学
  • 基金资助:
    湖南省教育厅重点课题资助项目(08A045)

Synthesis of 2,6-Di(2’-imidazoline-2’-yl)Pyridine under Microwave Irradiation and Interaction with DNA

ZHANG Jin-Yan1, XIAO Xiao-Ming1*, TAN Nian-Yuan2, XU Sha-Sha1, OUYANG Ze-Ying1   

  1. (1.College of Chemistry and Chemical Engineering,Hunan Normal University,Changsha 410081;
    2.College of Chemistry and Chemical Engineering,Hunan Institute of Engineering,Xiangtan)
  • Received:2009-08-13 Revised:2009-10-19 Published:2010-06-10 Online:2010-06-10

摘要:

在微波辐射和无催化剂条件下,由吡啶-2,6-二甲酸与乙二胺反应合成了2,6-二(2′-咪唑啉-2′-基)吡啶,并用红外光谱、质谱、核磁共振、熔点分析测试技术对化合物的组成和结构进行了分析与表征。 考察了反应溶剂、反应物比及微波辐射功率。 结果表明,不同溶剂对反应产物和副产物的比例有明显影响,最佳溶剂为乙二醇,最佳反应条件为:原料摩尔比1∶2.7,微波功率450 W,辐射时间65 min,温度130 ℃,总收率71.2%。 通过紫外吸收光谱和黏度测定了其与DNA的相互作用,测得键合常数Kb=(9.60±0.05)×104 L/mol,较常见的键合常数小。 推测化合物与DNA可能是以氢键作用与DNA沟面结合。

关键词: 二(咪唑啉基)吡啶, 乙二胺, 微波辐射, 合成, DNA

Abstract:

2,6-Di(2′-imidazoline-2′-yl)pyridine, even though it is not fully aromatic, has the same distribution of heteroatoms as 2,6-di(2′-benzimidazol-2′-yl)pyridine and has been synthesized from pyridine 2,6-dicarboxylic acid and ethylenediamine under microwave irradiation and without catalyst. The composition and structure of the product were identified and characterized by IR, mass spectrometry, 1H NMR, 13C NMR and melting point determination. The ratio of products and byproduct was found to be different under different experimental conditions(solvents, proportion of reacting mass, power of microwave irradiation). Among them, solvents have very obvious effects on the ratio of product and byproduct. The experimental results indicate that the best solvent is ethylene glycol. The optimal reaction condition are follows:molar ratio of raw materials 1∶2.7, microwave power 450 W, irradiation time 65 min, irradiation temperature 130 ℃ and the overall yield 71.2%. The binding of this compound with calf thymus DNA was investigated by UV and viscosity measurements. The binding constant Kb is meaused to be (9.60±0.05)×104 L/mol, which is lower than those observed for typical classical intercalators. The results of viscosity measurement reveal that the presence of 2,6-di(2′-imidazoline-2′-yl)pyridine has no obvious effect on the relative viscosity of DNA. It may bind to DNA by hydrogen bonding and grooveface binding.

Key words: di(imidazolineyl)pyridine, ethylenediamine, microwave irradiation, synthesis, DNA

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