1-脱氢松香酰基-3-芳酰胺基硫脲及其1,3,4-噻二唑类衍生物的合成及抑菌活性

Synthesis and Antibacterial Activity of 1-Dehydroabieticacyl-3-aroylthiosemicarbazides Compounds and Their 1,3,4-Thiadiazole Derivatives

以广西的优势资源松香为原料，脱氢松香酸与亚硫酰氯在回流条件下反应6h，所得产物与硫氰化钾回流反应1．5h，得到脱氢松香酰异硫氰酸酯，产率52％；然后与芳甲酰肼反应，得到一系列的1-脱氢松香酰基-3-芳酰胺基硫脲（4），产率39％～84％；最后用醋酸关环得到5．芳基-2．脱氢松香酰胺基-1，3，4-噻二唑（5），产率49％．87％：化合物4和化合物5的结构经IR、NMR测试技术分析确认，并用X射线衍射法测定了化合物5b的晶体结构。经初步生物活性测试表明，化合物4c、4f、5f在质量浓度为100mg／L时，对枯草杆菌和大肠杆菌有一定的抑制作用。

Dehydroabietic acid was refluxed with thionyl chloride for 6 h to yield acetyl chloride, which was refluxed with KSCN in anhydrous acetonitrile for 1. 5 h to provide dehydroabieticacyl isothiocyanate 3 in a yield of 52%. A series of 1-dehydroabieticacyl-3-aroylthiosemicarbazides 4 were obtained from the reaction of compound 3 with each of 4-substituted benzoylhydrazides in yields of 39% - 84%, and compounds 4 were treated under the catalysis of glacier acetic acid, giving their ring closure products 5-aryl-2-dehydroabieticacyl. amido-1,3,4-thiadiazoles 5 in 49% -87% yields. All the target compounds were characterized by IR, ^1H NMR, and ^13C NMR; the crystal structure of 5b was analyzed by X-ray crystallography. The preliminary biological tests showed that some of the title compounds（4c, 4f, 5f） possessed a fungicidal activity against B. subtilis and E. coli at test concentration（ 100 mg/L）.