多硫代丙酰胺的合成及其抑菌与海洋防污性能

Research on the Synthesis of Thiopropionamide Compounds and Their Bacteriostatic and Antifouling Property

以丙烯酸甲酯和烷基伯胺为原料,经过亲核加成反应和酯的胺解反应,合成了N,N-二甲基二硫代二丙酰胺(Ⅰa)、N,N-二乙基二硫代二丙酰胺(Ⅰb)、N,N-二正丙基二硫代二丙酰胺(Ⅰc)、N,N-二正丁基二硫代二丙酰胺(Ⅰd)4个二硫代二丙酰胺化合物和N,N-二甲基三硫代二丙酰胺(Ⅱa)、N,N-二乙基三硫代二丙酰胺(Ⅱb)、N,N-二正丙基三硫代二丙酰胺(Ⅱc)、N,N-二正丁基三硫代二丙酰胺(Ⅱd)4个三硫代二丙酰胺化合物,并通过核磁、质谱、红外光谱对其结构进行了表征。抑菌实验结果表明,三硫代二丙酰胺类化合物对大肠杆菌和金黄色葡萄球菌的抑菌性优于相应的二硫代二丙酰胺类化合物,其中Ⅱa和Ⅱb对两种菌的最小抑菌质量浓度均达到了0.03 g/L。一年的海上挂板实验表明,两类化合物均表现出较好的防污性能,其中,Ⅱa和Ⅱb的防污性能最好。

4 Dithiodipropionamides, N, N-di-methyl-dithiodipropionamide （I a ）, N, N-di-ethyl- dithiodipropionamide （ I b ）, N, N-di-propyl-dithiodi-propionamide （ I c ）, N, N-di-butyl- dithiodipropionamide （ Id ）, and 4 corresponding trithiodipropionamides, N, N-di-methyl-trithiodipropion- amide （Ha）, N, N-di-ethyl-trithiodipropionamide （ Ⅱb ）, N, N-di-propyl-trithiodipropionamide （ Ⅱc ）, and N,N-di-butyl-trithiodipropionamide （Ⅱd）, were synthesized from methyl acrylate and amine, and characterized by means of Mass spectrometer, NNR spectrometer and infrared spectrometer. The bioassay results of Escherichia coli and Staphylococcus aureus show that, compared with dithiodipropionamides, the trithiodipropionamides possessed better antibacterial activities, and the minimal inhibitory concentration values for the two bacteria of Ⅱa and Ⅱb reached about 0. 03 g/L. The study of their antifouling properties after they were submerged in the ocean for a year showed that all compounds displayed good antifouling property,with Ⅱa and Ⅱb displaying the best performance.