二氢嘧啶酮schiff碱的合成、表征及与牛血清白蛋白的相互作用
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江西教育厅科学技术研究项目(GJJ12703)和国家自然科学基金(21261020 和 21361022)


Synthesis, Characterization and Interaction with Bovine Serum Albumin of Schiff Base Containing Dihydropyrimidinone
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    摘要:

    本文以乙酰乙酸乙酯,对硝基苯甲醛和尿素为原料,通过缩合、还原反应,得到6-甲基-4-(4-氨基苯基)-5-乙氧基羰基-3,4-二氢嘧啶酮,再与芳香醛缩合得到了系列二氢嘧啶酮Schiff 碱衍生物(3a-3g),所得化合物结构经IR、1H NMR和13C NMR表征。用荧光光谱法研究了不同温度下3g与牛血清白蛋白(BSA)的相互作用,结果表明:3g对BSA有荧光猝灭作用;热力学参数表明:3g与BSA之间的主要作用力为疏水作用力;根据F鰎ster’s非辐射能量转移理论,求得3g与BSA之间的结合距离为2.59nm;同步荧光测试表明:3g使BS A分子构象发生了改变。

    Abstract:

    A series of Schiff base containing dihydropyrimidinone (3a-3g) has been synthesized by condensation reactions of aromatic aldehydes with 4-(4-aminophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidone, which prepared from ethyl acetoacetate, 4-nitrobenzaldehyde and urea through condensation and reduction reactions. The compounds were characterized by IR、1H NMR and 13C NMR. The interactions between 3g and bovine serum albumin (BSA) were investigated using fluorescence spectroscopy at different temperatures, the results revealed that 3g can effectively quench the intrinsic fluorescence of BSA; the corresponding thermodynamic parameters shown that the action forces were mainly hydrophobic interaction; the binding distance was estimated to be about 2.59 nm according to F鰎ster’s non-radioactive energy transfer theory; the synchronous fluorescence showed that the 3g induced conformational changes of BSA

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彭化南.二氢嘧啶酮schiff碱的合成、表征及与牛血清白蛋白的相互作用[J].精细化工,2016,33(12):

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  • 收稿日期:2016-07-06
  • 最后修改日期:2016-08-12
  • 录用日期:2016-10-11
  • 在线发布日期: 2016-12-13
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