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二氢嘧啶酮Schiff碱的合成及其与牛血清白蛋白的相互作用 被引量:2

Synthesis,Characterization and Interaction with Bovine Serum Albumin of Schiff Base Derivatives Containing Dihydropyrimidinone
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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Frster'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)~~
关键词 二氢嘧啶酮 SCHIFF碱 牛血清白蛋白 荧光猝灭 精细化工中间体 dihydropyrimidinone Schiff base bovine serum albumin fluorescence quenching finechemical intermediates
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  • 1周建峰,陆惠锋,顾惠丹,朱玉兰,屠树江.微波辐射下一步合成2-芳基-4,5-二苯基咪唑衍生物[J].应用化学,2005,22(8):918-919. 被引量:3
  • 2Lambardino J G, Wiseman E H. Preparation and anti- inflammatory activity of some nonacidic trisubstituted imidazoles [ J ]. J Med Chem, 1974,17 ( 11 ) : 1182 - 1188.
  • 3Laufer S A, Zimmermann W, Ruff K J. Tetrasubsti- tuted imidazole inhibitors of cytokine release:Probing substituents in the N-1 position [ J ]. J Med Chem, 2004,47(25) :6311 -6325.
  • 4Lee J C, Laydon J T, McDonnell P C, etal. A pro- tein kinase involved in the regulation of inflammatory cytokine biosynthesis [ J ]. Nature, 1994,372:739 - 746.
  • 5Shaabani A, Maleki A, Behnam M. Tandem oxidation process using eerie ammonium nitrate: Three-compo- nent synthesis of trisubstituted imidazdes under aero- bic oxidation conditions [J].Synth Commtm, 2009,39 (1) :102 -110.
  • 6DaSilva C M, DaSilva D L, Modolo L V, et al. Schiff bases: A short review of their antimlcrobial activities [J]. Journal of Advanced Research,2011,2(1) :1 -8.
  • 7Nawaz H, Akhter Z, Yameen S, et al. Synthesis and biological evaluations of some Schiff-base esters of fer- rocenyl aniline and simple aniline [ J ]. J Organomet Chem,2009,694(14) :2198 - 2203.
  • 8Hranjec M, Starcevic K, Pavellc S K, et al. Synthe- sis, spectroscopic charactefi-zation and antiprollfera- five evaluation in vitro of novel Schiff bases related to benzimidazoles [ J ]. Eur J Med Chem, 2011,46 ( 6 ) : 2274 - 2279.
  • 9Kimura M, Tsunenaga M, Takami S, et al. Develop- merit of functional imidazole derivatives: A potential ehemiluminescent chemosensor [ J ]. Bull Chem Soc Jpn,2005,78 ( 5 ) : 929 - 931.
  • 10杨国玉,王彩霞,黄立挺,徐翠莲.新型香豆素类衍生物的合成及其抗菌活性[J].合成化学,2011,19(3):337-340. 被引量:11

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