有机化学 ›› 2016, Vol. 36 ›› Issue (1): 143-150.DOI: 10.6023/cjoc201508007 上一篇    下一篇

研究论文

超声辐射下合成含苯并噻喃片段的新颖螺吲哚类化合物及其抗真菌活性

周冠a,b, 梁国超a,b, 钟一凡a,b, 韩晓燕a,b, 陈国锋c, 宋亚丽a,b   

  1. a 河北大学药学院 河北省药品质量控制重点实验室 保定071002;
    b 河北大学 教育部药物化学与分子诊断重点实验室 保定 071002;
    c 河北大学 化学与环境科学学院 保定 071002
  • 收稿日期:2015-08-06 修回日期:2015-09-23 出版日期:2016-01-25 发布日期:2015-09-25
  • 通讯作者: 宋亚丽 E-mail:yalisong@hbu.edu.cn
  • 基金资助:

    河北省药物质量分析控制重点实验室开放基金、“重大新药创制”国家科技重大专项(No. 2012ZX09103-101-057)资助项目.

Ultrasound Promoted Synthesis of Novel Substituted Spirooxindole Compounds Containing Thiochroman Moiety with Antifungal Activity

Zhou Guana,b, Liang Guochaoa,b, Zhong Yifana,b, Han Xiaoyana,b, Chen Guofengc, Song Yalia,b   

  1. a Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding 071002;
    b Key Laboratory of Medicinal Chemistry and Molecular Diagnosis, Ministry of Education, Hebei University, Baoding 071002;
    c College of Chemistry and Environmental Science, Hebei University, Baoding 071002
  • Received:2015-08-06 Revised:2015-09-23 Online:2016-01-25 Published:2015-09-25
  • Supported by:

    Project supported by the Open Project Program of Key Laboratory of Pharmaceutical Quality Control of Hebei Province, the National Major Scientific and Technological Special Project for ‘Significant New Drugs Development’ (No. 2012ZX09103-101-057).

探索了一种快速、高效的超声合成方法, 通过三组分一锅法合成了20个2'-氨基-2-氧代-5'H-螺[吲哚啉-3,4'-苯并噻喃[4,3-b]吡喃]-3'-甲腈类结构新颖的螺吲哚化合物. 所得到的化合物均由1H NMR, 13C NMR和HRMS确证. 研究了超声对产率和反应时间的影响. 采用微量稀释法对所合成的化合物进行了抗真菌活性的测定. 其中, 化合物4f对新生隐球菌、絮状表皮癣菌和总状毛霉的抑制活性均优于阳性对照药物氟康唑.

关键词: 硫色满酮, 超声, 螺吲哚, 三组分一锅法, 抗真菌活性

A rapid and efficient ultrasound-promoted one-pot synthesis of 2'-amino-2-oxo-5'H-spiro[indoline-3,4'-thiochromeno[4,3-b]pyran]-3'-carbonitrile compounds by one-pot three-component reaction had been developed. Structures of all products were characterized by 1H NMR, 13C NMR and HRMS. The effect of ultrasound on yield and reaction time had been studied to understand the role of ultrasound in the reaction. The antifungal activity was determined by micro dilution method. Compound 4f exhibited inhibitory activity to Cryptococcus neoformans, Epidermophyton floccosum and Mucor racemosus better than the positive control drug fluconazole.

Key words: thiochromanone, ultrasound, spirooxindole, one-pot three-component reaction, antifungal activity