摘要
以乙酰乙酸乙酯、对硝基苯甲醛和尿素为原料,通过缩合、还原反应,得到了6-甲基-4-(4-氨基苯基)-5-乙氧基羰基-3,4-二氢嘧啶酮(Ⅱ),再与芳香醛缩合,以71.5%~83.7%的收率制备了一系列二氢嘧啶酮Schiff碱衍生物(Ⅲa^g),产物结构经IR、1HNMR和13CNMR表征,并用荧光光谱法研究了不同温度下6-甲基-4-[4-(3-硝基苯亚甲基氨基)苯基]-5-乙氧基羰基-3,4-二氢嘧啶酮(Ⅲg)与牛血清白蛋白(BSA)的相互作用。结果表明:Ⅲg对BSA具有荧光猝灭作用。热力学参数表明:由于ΔH>0和ΔS>0,Ⅲg与BSA之间的主要作用力为疏水作用力;并且根据Frster's非辐射能量转移理论,得到了Ⅲg与BSA之间的结合距离为2.59 nm。同步荧光测试结果表明:Ⅲg使BSA分子构象发生了改变。
4-( 4-Aminophenyl ) -5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidone ( Ⅱ ) was prepared from ethyl acetoacetate,4-nitrobenzaldehyde and urea through condensation and reduction reactions. A series of Schiff base derivatives containing dihydropyrimidinone (Ⅲ a · g) with yields of 71.5% - 83.7% were obtained via condensation reactions between compound 11 and different substituted aromatic aldehydes. These compounds were characterized by IR, 1HNMR and 13 CNMR. The interactions between compound Ⅲ g and bovine serum albumin (BSA) were investigated using fluorescence spectroscopy at different temperatures. The results revealed that compound m g could effectively quench the intrinsic fluorescence of BSA. And the corresponding thermodynamic parameters ( AH 〉 0 and AS 〉 O) showed that the interaction between the two were mainly hydrophobic interaction. Meanwhile, the binding distance between compound Ⅲ g and BSA was about 2. 59 nm according to Ftrster's non- radioactive energy transfer theory. Furthermore, the synchronous fluorescence spectroscopy indicated that compound Ⅲg could induce conformational transitions of BSA.
出处
《精细化工》
EI
CAS
CSCD
北大核心
2016年第12期1434-1440,共7页
Fine Chemicals
基金
江西教育厅科学技术研究项目(GJJ12703)
国家自然科学基金(21261020
21361022)~~