N-取代苯基-卤代邻羟基苄胺的合成、表征及抑菌活性

通过卤代水杨醛与取代芳胺缩合、NaBH4还原, 合成了15种N-取代苯基-卤代邻羟基苄胺化合物, 其中14种未见报道. 化合物的结构经IR, 1H NMR, MS与元素分析表征确证. 抑菌测试表明, 在质量浓度为0.05%时, 化合物对白色念珠菌的抑菌率高达100%, 具有强抑菌活性, 对金黄色葡萄球菌、大肠杆菌有一定的抑菌活性. 该类化合物对不同菌株的抑菌活性具有明显的选择性和特异性, 是一类极具潜力的抗真菌化合物. 构效分析表明, 胺基苯环上取代基的类型对化合物抑菌活性有重要影响, 引入F, Cl等卤原子, 能显著增强化合物的抑菌活性, 而引入NO2, OCH3等强吸、供电基团, 能显著降低其抑菌活性; 邻羟基苯环上引入卤原子的类型和数量对化合物抑菌活性有一定影响, 5-溴代化合物比5-氯代化合物、3,5-二溴代化合物对大肠杆菌的抑菌活性更高.

Synthesis, Characterization and Antibacterial Activities of N-(Substituted phenyl)-halogeno-o-hydroxybenzylamines

Fifteen N-(substituted phenyl)-halogeno-o-hydroxybenzylamines were synthesized through halogeno-salicylaldehyde condensation with aromatic amines and reduction with NaBH4, respectively, and fourteen compounds of them are novel. The structures of all the compounds have been confirmed by 1H NMR, IR, MS techniques and elemental analysis. The result of preliminary bioassay showed that the title compounds had 100% inhibitory rate against Monilia albican at 0.05% mass concentration and a favorable extent of antibacterial activities against Escherichia coli and Staphylococcus aureus. This kind of com-pounds have obvious specificity antibacterial activities against different bacteria and they would be a good choice of antibacterial compounds against fungi. The analysis of structure-activity relationship showed that the antibacterial activities of title compounds were enhanced by the halogen groups but reduced by strong electron-donating and electron-withdrawing groups of the arylamine rings, such as NO2, OCH3. The types and numbers of halogen atoms on the hydroxyphenyl rings had impact on the antibacterial activities of title compounds, and 5-bromo-compounds had better antibacterial activities against Escherichia coli than 5-chloro and 3,5-dibromo-compounds.