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林产化学与工业 ›› 2015, Vol. 35 ›› Issue (1): 30-38.doi: 10.3969/j.issn.0253-2417.2015.01.005

• 研究报告 • 上一篇    下一篇

樟脑酸基苯磺酰胺类化合物的合成及抑菌活性研究

马献力1,2, 闵方倩1, 段文贵1, 李芳耀1,2, 刘陆智1, 岑波1, 雷福厚3   

  1. 1. 广西大学 化学化工学院, 广西 南宁 530004;
    2. 桂林医学院 药学院, 广西 桂林 541004;
    3. 广西林产化学与工程重点实验室, 广西 南宁 530008
  • 收稿日期:2013-12-03 出版日期:2015-02-25 发布日期:2015-03-05
  • 通讯作者: 段文贵(1964-),广西资源人,教授,博士生导师,主要从事天然资源化学和有机合成研究;E-mail:wgduan@gxu.edu.cn。 E-mail:wgduan@gxu.edu.cn
  • 作者简介:马献力(1978-),男,河南叶县人,博士生,从事天然产物改性及有机合成研究
  • 基金资助:
    国家自然科学基金资助项目(31260164);广西高校科学技术研究重点项目(ZD2014098);广西林产化学与工程重点实验室开放基金项目(GXFC12-01)

Synthesis and Fungicidal Activity of Camphoric Acid-based Benzenesulfonamide Compounds

MA Xian-li1 2, MIN Fang-qian1, DUAN Wen-gui1, LI Fang-yao1 2, LIU Lu-zhi1, CEN Bo1, LEI Fu-hou3   

  1. 1. College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China;
    2. College of Pharmacy, Guilin Medical University, Guilin 541004, China;
    3. Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008, China
  • Received:2013-12-03 Online:2015-02-25 Published:2015-03-05

摘要: 以樟脑酸为原料,经过脱水反应制备樟脑酸酐。将取代苯磺酰氯与乙二胺反应得到N-芳磺酰基乙二胺,再与樟脑酸酐反应,合成得到11个新型樟脑酸基苯磺酰胺类化合物,分别为:樟脑酸基苯磺酰胺(4a)、樟脑酸基对甲基苯磺酰胺(4b)、樟脑酸基间甲基苯磺酰胺(4c)、樟脑酸基对甲氧基苯磺酰胺(4d)、樟脑酸基间甲氧基苯磺酰胺(4e)、樟脑酸基对氟苯磺酰胺(4f)、樟脑酸基邻氟苯磺酰胺(4g)、樟脑酸基对氯苯磺酰胺(4h)、樟脑酸基间氯苯磺酰胺(4i)、樟脑酸基对溴苯磺酰胺(4j)和樟脑酸基间溴苯磺酰胺(4k)。目标产物的适宜合成条件为:以无水乙醇作溶剂,反应温度80 ℃,n(樟脑酸酐):n(N-芳磺酰基乙二胺)为1:1.2。利用FT-IR 、1H NMR、13C NMR 和ESI-MS等多种手段对目标化合物进行结构表征。初步的生物活性测试表明,在50 mg/L质量浓度下,大部分化合物具有一定的抑菌活性,其中化合物4a和4e对苹果轮纹病菌的抑制率达94.8 %,化合物4h对番茄早疫病菌的抑制率达86.9 %。

关键词: 樟脑酸, 磺酰胺, 合成, 抑菌活性

Abstract: Camphoric anhydride was prepared via dehydration reaction using camphoric acid as starting material. Then, N-aryl sulfonyl ethyenediamines were synthesized by the reaction of ethylenediamine with substituted benzenesulfonyl chlorides, followed by the reaction of camphoric anhydride with N-aryl sulfonyl ethyenediamines to obtain eleven novel camphoric acid-based benzenesulfonamide compounds:camphoric acid-based benzenesulfonamide(4a), camphoric acid-based p-methyl-benzenesulfonamide(4b), camphoric acid-based m-methyl-benzenesulfonamide(4c), camphoric acid-based p-methoxy-benzenesulfonamide(4d), camphoric acid-based m-methoxy-benzenesulfonamide(4e), camphoric acid-based p-fluoro-benzenesulfonamide(4f), camphoric acid-based o-fluoro-benzenesulfonamide(4g), camphoric acid-based p-chloro-benzenesulfonamide(4h), camphoric acid-based m-chloro-benzenesulfonamide(4i), camphoric acid-based p-bromo-benzenesulfonamide(4j), and camphoric acid-based m-bromo-benzenesulfonamide(4k). The synthetic conditions were investigated preliminarily. The suitable synthetic conditions for the target compounds were as follows:anhydrous ethanol as solvent, reaction temperature 80 ℃, n(camphoric anhydride):n(N-aryl sulfonyl ethyenediamine) 1:1.2. The target compounds were characterized by FT-IR, 1H NMR, 13C NMR and ESI-MS, respectively. The preliminary bioassay showed that most of the title compounds exhibited certain fungicidal activity at the concentration of 50 mg/L, in which compounds 4a and 4e had inhibition rate of 94.8 % against Physalospora piricola, and compound 4h had inhibition rate of 86.9 % against Alternaria solani.

Key words: camphoric acid, sulfonamide, synthesis, fungicidal activity

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