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

doi:10.6023/cjoc201508007

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (1): 143-150.DOI: 10.6023/cjoc201508007 Previous Articles Next Articles

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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

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 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 Guan^a,b, Liang Guochao^a,b, Zhong Yifan^a,b, Han Xiaoyan^a,b, Chen Guofeng^c, Song Yali^a,b

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 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).

1. Ultrasound Promoted Synthesis of Novel Substituted Spirooxindole Compounds Containing Thiochroman Moiety with Antifungal Activity.PDF(2399KB)

Abstract

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

Cite this article

Zhou Guan, Liang Guochao, Zhong Yifan, Han Xiaoyan, Chen Guofeng, Song Yali. Ultrasound Promoted Synthesis of Novel Substituted Spirooxindole Compounds Containing Thiochroman Moiety with Antifungal Activity[J]. Chin. J. Org. Chem., 2016, 36(1): 143-150.

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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

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

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