摘要
丁香醛,亚膦酸二异丙酯分别与苯胺、对甲苯胺、间甲苯胺和间溴苯胺通过Kabachnik-Fields反应,在无溶剂无催化剂条件下一锅合成了4个α-氨基丁香基膦酸酯化合物1~4。采用1H NMR,13 C NMR和IR对1~4进行了结构鉴定。对化合物1~4进行了抑菌活性、紫外及荧光性质测定。结果表明,化合物1~4在质量浓度为25~200 mg/L范围内均对大肠杆菌、枯草芽孢杆菌和金黄色葡萄球菌表现出不同程度的抑菌活性,其中,化合物1~4在质量浓度为25~100 mg/L时对枯草芽孢杆菌的抑制作用均优于阳性对照氯霉素。此外,化合物1~4在物质的量浓度为10μmol/L时的最大紫外吸收波长均接近250 nm。荧光性能实验结果表明,在化合物1~4物质的量浓度为0.1~200.0μmol/L时,化合物1~4的最大发射波长为625~700 nm,最大光量子产率所对应的物质的量浓度分别为20.0,50.0,100.0和0.1μmol/L。
Fourα-amino-syringyl-phosphonates 1~4 were synthesized by a solvent and catalyst free one pot Kabachnik-Fields reaction of syringaldehyde,diisopropyl phosphite,and aniline,p-methyl aniline,m-methyl aniline,and m-bromoaniline,respectively.The structures were identified by 1H NMR,13 C NMR and IR.The antibacterial activity,UV and fluorescent property of 1~4 were measured.The samples 1~4 exhibited antibacterial activity to Escherichia coli,Bacillus subtilis,and Staphylococcus aureus at the mass concentration from 25 to 200 mg/L.And,1~4 inhibited Bacillus subtilis stronger than that of chloromycetin at the mass concentration range of 25~100 mg/L.UV absorb wavelength of 1~4 is about 250 nm and the maximum fluorescent emission wavelength of 1~4 is at 625~700 nm with the concentration range of 0.1~200.0μmol/L.The concentration with the maximum light quantum yield of 1~4 was 20.0,50.0,100.0 and 0.1μmol/L,respectively.
作者
历宇
钱梦圆
何丹凤
马文辉
唐万侠
Li Yu;Qian Mengyuan;He Danfeng;Ma Wenhui;Tang Wanxia(Faculty of Chemistry and Chemical Engineering,Heilongjiang Industrial Hemp Processing Technology Innovation Center,Qiqihar University,Qiqihar,Heilongjiang,161006,China;College of Science,Qiongtai Normal University,Haikou,Hainan,571100,China)
出处
《化学世界》
2025年第4期240-245,共6页
Chemical World
基金
国家自然科学基金(No.22266028)
黑龙江省优势特色学科专项(No.YSTSXK201846)资助项目。
