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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (02): 254-259. 上一篇    下一篇

研究论文

伞型酮类似物的合成及抗菌作用

章维华*，蒋木庚   

  1. (南京农业大学理学院 南京 210095)
  • 收稿日期:2009-02-05 修回日期:2009-08-12 发布日期:2010-03-30
  • 通讯作者: 章维华 E-mail:zhwh@njau.edu.cn
  • 基金资助:

    国家自然科学基金资助项目（20502011）;教育部重点实验室绿色农药与生物工程重点开放实验室资助项目（2007GDGP0101）

Synthesis and Antifungal Activity of Umbelliferone Analog

ZhangWeihua* Jiang Mugeng   

  1. (College of Science, Nanjing Agricultural University, Nanjing 210095)
  • Received:2009-02-05 Revised:2009-08-12 Published:2010-03-30
  • Contact: ZHANG Wei-Hua E-mail:zhwh@njau.edu.cn

PDF

1300

被引次数

29 | 7

2-甲基间二酚或5-甲基间二酚分别与dl-苹果酸或乙酰乙酸乙酯, 在浓硫酸催化下, 经Peachmann缩合反应得到伞型酮(7-羟基香豆素)类似物5～7. 5～7经甲基化得新化合物5a, 6a和7a; 经Williamson反应, TBAB(四正丁基溴化铵)相转移催化合成了14个新的香豆素类化合物5b～5e, 6b～6f, 7b～7f. 经IR, MS, 1H NMR及元素分析对所有化合物的结构进行了表征. 初步生物活性实验结果表明, 在50 μg/mL浓度下, 化合物6对辣椒疫霉病菌(Phytophythora capsici)抑制率达58.5%, 化合物7c对番茄灰霉病菌(Botrytis cinerea)抑制率为54.0%, 化合物6c对水稻纹枯病菌(Rhizoctonia solani)的抑制率达83.7%.

关键词: 伞型酮, 香豆素, 合成, 抑菌活性

Resorcinol was reacted with dl-malic acid or ethyl acetoacetate under the catalysis of sulfuric acid via Pechmann condensation to produce three umbelliferone (7-hydroxycoumarin) analogs 5～7. 5a, 6a and 7a were synthesized by methylation of 5～7. Fourteen new coumarin compounds 5b～5e, 6b～6f and 7b～7f were prepared from the intermediates and alkyl halides via Williamson reaction using TBAB (tetrabutylammonium bromide) as catalyst. The structures of all those new compounds were confirmed by 1H NMR, IR, MS techniques and elemental analysis. The preliminary bioassay showed that, compound 6 had inhibitory activity 58.5% against Phytophythora capsici, 7c had antifungal activity 54.0% against Botrytis cinerea and 6c had antifungal activity 83.7.0% against Rhiazoctonia solani at 50 μg/mL.

Key words: umbelliferone, coumarin, synthesis, inhibitory activity