有机化学 ›› 2011, Vol. 31 ›› Issue (12): 2052-2060. 上一篇    下一篇

研究论文

硝基或氯代Blebbistatin化合物的合成

孙兴芳,陈长宝,庄园,周杰*   

  1. (山东农业大学化学与材料科学学院 泰安 271018)
  • 收稿日期:2011-03-19 修回日期:2011-05-17 出版日期:2011-12-25 发布日期:2011-07-15
  • 通讯作者: 周杰 E-mail:zhoujie@sdau.edu.cn

Synthesis of Nitro- or Chloro-substitutional Bleb-bistatin Compounds

SUN Xing-Fang, CHEN Chang-Bao, ZHUANG Yuan, ZHOU Jie   

  1. (College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018)
  • Received:2011-03-19 Revised:2011-05-17 Online:2011-12-25 Published:2011-07-15

以2-氨基-5-硝基苯甲酸或4-氯苯甲酸、1-苯基-2-吡咯烷酮为原料, 经过酯化、亚胺合成、关环、不对称合成四步反应合成了2种新的Blebbistatin化合物: 3a-羟基-6-硝基-1-苯基-1,2,3,3a-四氢-吡咯并[2,3-b]-喹啉-4-酮或3a-羟基-7-氯-1-苯基-1,2,3,3a-四氢-吡咯并[2,3-b]-喹啉-4-酮. 通过IR, 1H NMR, 元素分析证实其结构, 并测定了一些重要中间体的单晶结构. 初步研究化合物的光学性质发现, 所合成的新Blebbistatin化合物的紫外吸收与荧光发射强度均比前人合成的Blebbistatin化合物高.

关键词: Blebbistatin, 合成, 紫外吸收光谱, 荧光发射光谱

Using 2-amino-5-nitro-benzoic acid or 4-chloro-benzoic acid and 1-phenyl-2-pyrrolidinone as initial materials, two new blebbistatin compounds, 3a-hydroxy-6-nitro-1-phenyl-1,2,3,3a-tetrahydropyr- rolo[2,3-b]quinolin-4-one and 3a-hydroxy-7-chloro-1-phenyl-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]quinolin- 4-one, were synthesized through four steps, including esterification, imine synthesis, cyclization and asymmetric synthesis. Their structures were confirmed by IR, 1H NMR techniques and elemental analysis. The single crystals of some important intermediates were determined. Their optical properties were prelimi-narily studied, and it was discovered that the UV-vis absorption and fluorescence emission intensities of the new compounds were higher than the compounds reported previously.

Key words: blebbistatin, synthesis, UV-vis absorption spectra, fluorescence emission spectra