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

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.

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

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.