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化学学报
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化学学报 ›› 2008, Vol. 66 ›› Issue (24): 2717-2724. 上一篇    下一篇

研究论文

1-脱氢松香酰基-3-取代硫脲以及5-(脱羧脱氢松香-4-基)-3-芳氨基- 1H-1,2,4-三唑化合物的合成与生物活性

苏桂发*,a 霍丽妮a 陈 睿b 赵丰丽b 关一富a

  

  1. (a广西师范大学化学化工学院 药用资源化学与药物分子工程教育部重点实验室 桂林 541004)
    (b广西师范大学生命科学学院 桂林 541004)

  • 投稿日期:2007-09-07 修回日期:2007-12-21 发布日期:2008-12-28
  • 通讯作者: 苏桂发

Synthesis and Biological Activities of 1-Dehydroabietoyl-3-substituted Thiourea and Related 4-Decarboxy-4-{3-[(un)substituted anilino]-1H-1,2,4-triazol-5-yl}dehydroabietic Acid Derivatives

SU, Gui-Fa *,a HUO, Li-Ni a CHEN, Rui b ZHAO, Feng-Li b GUAN, Yi-Fu a   

  1. (a Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources of State Education Ministry, College of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin 541004)
    (b College of Life Science, Guangxi Normal University, Guilin 541004)
  • Received:2007-09-07 Revised:2007-12-21 Published:2008-12-28
  • Contact: SU, Gui-Fa

PDF

1301

被引次数

25

以广西的优势资源松香为原料, 脱氢松香酸与亚硫酰氯、硫氰化钾分别在回流条件下反应6 h和1.5 h, 得到脱氢松香酰异硫氰酸酯, 产率52%; 然后与胺在加热回流条件下反应1.5 h, 得到11种1-脱氢松香酰基-3-取代硫脲4, 产率63%～94%; 4a～4f 分别与水合肼在搅拌下回流反应3～6 h, 得到6种5-(脱羧脱氢松香-4-基)-3-芳氨基-1H-1,2,4-三唑化合物5, 产率70%～94%; 所有化合物的结构均经IR, 1H NMR, 13C NMR和元素分析确认. 初步生物活性测试表明, 4e, 4f, 4j, 5b对枯草杆菌抑菌率较高, 特别是4j在浓度为50 mg/L时就达到较好效果; 4b, 4h, 4i, 5e在100 mg/L时对大肠杆菌的抑菌效果较好.

关键词: 脱氢松香酸, 1-脱氢松香酰基-3-取代硫脲, 5-(脱羧脱氢松香-4-基)-3-芳氨基-1H-1,2,4-三唑化合物

In an attempt to find novel bioactive compounds, a series of 1-dehydroabietoyl-3-substituted thiourea 4 and 4-decarboxy-4-{3-[(un)substituted anilino]-1H-1,2,4-triazol-5-yl}dehydroabietic acid 5 were synthesized from dehydroabietic acid. Compounds 4a～4k were obtained from the reaction of dehydroabietic acyl isothiocyanate with amines, and 5a～5f were prepared by the reaction of 4 with hydrazine hydrate. The structures of the title compounds were confirmed by IR, 1H NMR and 13C NMR. The preliminary biological tests display that some of the title compounds (4j, 4e, 4f and 5b) possess a fungicidal activity against B. subtilis at a test concentration (for 4j: 50 mg/L; for 4e, 4f, 5b: 100 mg/L); 4b, 4h, 4i and 5e possess a fungicidal activity against E. coli at a test concentration of 100 mg/L.

Key words: dehydroabietic acid, 1-dehydroabietoyl-3-substituted thiourea, 4-decarboxy-4-{3- [(un)substituted anilino]-1H-1,2,4-triazol-5-yl}dehydroabietic acid