N-(5-氯-2-羟苄基)氨基酸酯的合成、表征及抑菌活性

Synthesis,Characterization and Antibacterial Activities of 5-Chloro-o-hydroxybenzyl Amino Acid Esters

以5-Cl水杨醛和L-苯丙氨酸、L-亮氨酸及L-甘氨酸的脂肪酸酯为原料,通过碱催化的席夫碱缩合反应,合成了6种N-(5-氯-2-羟苄基)席夫碱氨基酸酯及其还原产物N-(5-氯-2-羟苄基)氨基酸酯。化合物的结构及组成经过IR、1HNMR和元素分析测试技术进行了表征。合成的席夫碱及其还原产物对革兰氏阴性菌、革兰氏阳性菌及真菌均有不同程度的抑制作用。质量分数为0.01%的N-(5-氯-2-羟苄基)席夫碱氨基酸酯对大肠杆菌的抑菌率达90%以上,而N-(5-氯-2-羟苄基)氨基酸酯对金黄色葡萄球菌的抑菌率也在90%以上,均为强抑菌活性,其中N-(5-氯-2-羟苄基)苯丙氨酸酯的抑菌率达98%以上。

A series of 5-chloro-o-hydroxyphenyl amino acid esters schiff bases was designed and synthesized by the condensation of chlorinated salicylaldehyde with amino acid esters including phenylalamine methyl （ethyl） ester,leucine methyl（ethyl） ester and glycinate methyl（ethyl） ester,which were subjected to further reduction form 5-chloro-o-hydroxybenzyl amino acid esters.The structures of these compounds were characterized by IR,1↑H NMR and elemental analysis.The antibacterial activity assay indicates that these compounds resist different bacteria to different degrees.The result of preliminary bioassay shows that at a mass concentration of 0.01% ,the inhibitory rate of the 5-chloro-o-hydroxyphenyl amino acid esters schiff base against Escherichia coli is over 90% and the inhibitory rate of the 5-chloro-o-hydroxybenzyl amino acid esters against Staphylococcus aureus is also over 90% .In addition,the inhibitory rate of 5-chloro-o-hydroxybenzyl phenylalamine ester against Staphylococcus aureus can be as high as 98% .