摘要
研究新型席夫碱[（E）-1-（3,5-二氯-2-羟基-4-甲氧基苯基）亚乙氨基]乙酸乙酯的合成、表征及生物活性。以乙腈为溶剂,3,5-二氯-2-羟基-4-甲氧基苯乙酮与甘氨酸乙酯物质的量比为1：3,反应温度和时间分别为25℃和1 h时,最大反应收率为90.97%。采用UV,IR,LCMS,1H NMR,荧光光谱及X射线单晶衍射等方法表征了产物的分子及晶体结构。紫外可见吸收光谱表明：目标化合物的甲醇溶液在330 nm和410 nm处分别出现烯醇式和酮式亚胺互变异构吸收峰;在甲醇、N,N-二甲基甲酰胺（DMF）、二氯甲烷和氯仿溶液中具有蓝紫色荧光,最佳荧光激发和发射波长分别为332～372 nm和451～499 nm,且随溶剂极性增大,荧光激发峰红移;目标化合物晶体属单斜晶系,空间群为P21/c,β=91.131（5）o,a=4.571 1（18）A,b=30.302（12）А,c=10.602（4）A,V=1 468.2（10）А3,Dc=1.448×103kg·m-3,Z=4,R1=0.058 9,w R2=0.123 2;具有一定抗氧化作用,浓度为62.50 mg·L-1时,对1,1-二苯基-2-苦基肼（DPPH）自由基清除率达27.95%;对大肠杆菌和金黄色葡萄球菌具有一定抑制作用,最低抑菌浓度（MIC）均为1.0×10-6mol·L-1;对铜绿假单胞菌基本无抑制作用。
The synthesis, characterization and bioactivity of a new Schiff base ethyl [（E）-1- （3, 5-dichloro-2- hy- droxy-4-methoxyphenyl）ethylidene]aminoacetate was studied. The maximum yield 90.97% was obtained by the reaction of 3, 5-dichloro-2-hydroxy-4-methoxyacetophenone with glycine ethyl ester hydrochloride in 1： 3mo- lar ratio under room temperature in acetonitrile for 1 h. The molecular and crystal structure of the product was characterized by UV, IR, LCMS, IH NMR, fluorescence spectra and X-ray single crystal diffraction, respectively. The UV spectra of the target compound in methanol solution indicated that the maximum absorption of the π-π＊ electron transition of the enol and keto tautomer of the target compound appeared at 330 nm and 410 urn, re- spectively. It has blue or violet fluorescence in methanol, DMF, dichloromethane and chloroform solution, and the maximum excitation and emission wavelength was at 332-372 nm and 451-499 nm, respectively. The target com- pound was crystallized in monoclinic system, space group P21/c, with β = 91.131（5）°, a = 4.571 1（18） A, b = 30.302（12） A, c = 10.602（4） A, V= 1 468.2（10） A3, Dc = 1.448×10^3 kg-m3, Z= 4, R, = 0.058 9, wR2 = 0.123 2.It was a mild antioxidant, the maximum scavenging rate of 1, 1-diphenyl-2-picryl hydrazyl （DPPH） free radicals was 27.95% under the concentration of 62.50 mg. L-1. The target compound had antibacterial activity against Esch- erichia coli and Staphylococcus aureus, both minimal inhibitory concentration （MIC） were 1.0x 10-6 mol·L-1, but had no antibacterial activity against Pseudomonas aeruginosa.
出处
《安徽工业大学学报（自然科学版）》
CAS
2015年第4期330-337,共8页
Journal of Anhui University of Technology（Natural Science）
基金
国家自然科学基金项目(81402511)
安徽省高校自然科学研究重点项目(KJ2012A050)
安徽省研究生"千人联合培养"计划项目(20130007)
安徽省大学生创新创业训练计划(AH201510360152)
