超声波辅助Huisgen-Click反应在白杨素改造中应用及其与蛋白的相互作用研究
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摘要
氮杂环类药物在目前临床使用的药物中占有很大的比例,全球药品销售前200名的药物中一半以上结构中存在氮杂环。1,2,3-三氮唑作为氮杂环中一类,具有广泛的生理活性,如抗HIV、抗菌、治疗神经性精神错乱、选择性β3肾上腺素受体激动剂等。近年来,1,2,3-三氮唑作为一种重要的药效团,已经被用于多肽、DNA、RNA和糖类等化合物结构修饰中,并表现出良好的效果。白杨素是一种重要的天然黄酮类化合物,具有抗菌,抗癌,抗氧化等广泛的生物活性,但因其在肠道内吸收甚少等原因导致活性降低。亚铜盐催化的Huisgen-Click环加成反应,能够温和的、高产率、高区域选择性的生成1,2,3-三氮唑类衍生物,因此该反应的出现对于药物合成、化合物的结构修饰等具有巨大的促进作用,受到人们极大的关注。
本文首先对近年来Huisgen-Click反应的研究进展和应用情况、白杨素的结构修饰的研究进展情况分别进行了总结。然后通过优化实验条件,在超声辅助下通过Huisgen-Click反应首次将其运用到天然产物白杨素的结构改造中,合成了一系列含有1,2,3-三氮唑药效团的白杨素衍生物,并采用荧光光谱法和紫外可见光谱法研究了其与蛋白的相互作用情况。
1、以苯基炔丙基醚和叠氮乙酸乙酯的反应为模板,系统考查了催化剂、溶剂、碱和配体存在下超声波对反应的速度和产率的影响,对反应条件进行了优化。结果表明：(1)超声波对反应有加速作用,产率也有相应的提高；用水作为反应溶剂优于其它反应溶剂；在原位产生亚铜离子的催化体系中醋酸铜优于其它二价铜盐；(2)在优化的实验条件下,合成了32个1,2,3-三氮唑类化合物,其中20个为新化合物,其结构经过IR, ESI MS, NMR的确认；(3)考查了超声波对反应选择性的影响,通过HMBC, COSY, NOE等2D NMR图谱对化合物的1,4-取代进行了确认。
2、以天然产物白杨素为母体,通过超声辅助下的Husigen-Click环加成反应将1,2,3-三氮唑药效团引入到白杨素的结构修饰中,对反应条件进行了优化。以硫酸铜／抗坏血酸钠为催化剂,叔丁醇／水等体积为溶剂,合成了14个新型的白杨素1,2,3-三氮唑衍生物,其结构经过IR, ESI MS, NMR等进行了确认,并对化合物的波谱特征进行了总结。
3、利用荧光光谱和紫外可见光谱法研究了5个白杨素1,2,3-三氮唑衍生物与牛血清蛋白、溶菌酶的相互作用。实验表明：白杨素1,2,3-三氮唑衍生物对蛋白的荧光有猝灭作用,且猝灭过程是由于形成了复合物而引起的静态猝灭；小分子与蛋白之间的作用力主要是静电和疏水作用力；白杨素的衍生物2-5-1与牛血清蛋白的结合常数比白杨素增强了5.5倍,说明1,2,3-三氮唑药效团的存在,增加了小分子与蛋白之间的相互作用。
N-heterocyclic drugs account for a large proportion of currently clinical used drugs and more than half of top 200 global pharmaceutical drugs contains the N-heterocyclic structure.1,2,3-triazoles, as a member of N-heterocycles, bear various biological activities such as anti-HIV, anti-microbial, anti-allergic, and selectiveβ3 adrenergic receptor agonist. Recently,1,2,3-triazole moiety, as an important pharmacophore, was widely introduced in to peptides, DNA, RNA and carbohydrates and so on. And the modifications showed good results. Chrysin, an important naturally occurring flavonoid, bears multiple biological activities, such as anti-viral, antibacterial, antioxidant, anticancer activities. However, the activity of chrysin decreased due to its poor absorption in the intestine. Copper(I)-catalyzed 1, 3-dipolar Huisgen cycloaddition (CuAAC) reaction of azides and terminal alkynes gained much attention because it is an mild, high yield, good regioselectivity method and greatly used in synthesis and structural modification of durgs.
In the work describe in this chapter 1, the recently development and applications of Huisgen-Click reaction, the structure modifications of chrysin were reviewed. In the following chapters,1,2,3-triazole moiety was firstly coupled with chrysin by an optimized ultrasound-assisted Huisgen-Click reaction and a series of chrysin derivatives linked with 1,2,3-trizaole moiety were synthesized. The non-covalent interaction between those chrysin derivatives and BSA was studied by fluorescence spectroscopy and UV absorption spectroscopy.
1、The reaction between propargyl phenyl ether and ethyl 2-azidoacetate was selected as a model reaction for investigating the influence of ultrasound on the rate and yield of cycloaddition with different catalysts, solvents, base and ligand. The reaction condition was optimized through a series of experiments. The results are as follows:(1) Ultrasound irradiation not only acceletates the cycloadditon rate but also improves the product yield. Water is the better solvent than other tested solvents. Cu(OAc)2 is better than other tested Cu(II) salts in the catalyst system where Cu(I) ion is generated in situ; (2) Thirty two 1,4-disubstituted triazole derivatives were synthesized under the optimized condition, twenty of which are new compounds. Their structures were confirmed by IR, ESI MS and NMR. (3) The influence of ultrasound on the regioselectivity of the reaction was studied. The structure of 1,4-disubstituted triazole derivative was confirmed by 2D NMR such as HMBC, COSY, NOE.
2、A series of chrysin derivatives linked with 1,2,3-triazoles were synthesized using the CuAAC reaction under optimized conditions. The 1,3-dipolar cycloaddition reaction can be successfully carried out using CuSO4/sodium ascorbate as the catalyst,t-BuOH-H2O (1:1 v/v) as the solvent under the help of ultrasound at room temperature. Structures of the novel 14 compounds were determined by NMR, ESI MS, IR and elemental analysis. All the 1H、13C chemical shifts of the compound were assigned using 2D NMR techniques, including DEPT、1H-1H COSY、13C-1H HSQC、13C-1H HMBC.
3、The interaction of five novel chrysin derivatives with Bovine Serum Albumin, Lysozyme were studied using fluorescence spectroscopy and UV absorption spectroscopy. The result showed that small molecules are able to couse fluorescent of proteins quench, and the quenching process is static quenching. Electrostatic and hydrophobic forces are mainly involved in the initial interaction. Binding constant between 2-5-1 and BSA is as 5.5 times as that between chrysin and BSA, which indicates that the introduced 1,2,3-triazole enhanced the interaction between the small molecules with BSA.
本文首先对近年来Huisgen-Click反应的研究进展和应用情况、白杨素的结构修饰的研究进展情况分别进行了总结。然后通过优化实验条件,在超声辅助下通过Huisgen-Click反应首次将其运用到天然产物白杨素的结构改造中,合成了一系列含有1,2,3-三氮唑药效团的白杨素衍生物,并采用荧光光谱法和紫外可见光谱法研究了其与蛋白的相互作用情况。
1、以苯基炔丙基醚和叠氮乙酸乙酯的反应为模板,系统考查了催化剂、溶剂、碱和配体存在下超声波对反应的速度和产率的影响,对反应条件进行了优化。结果表明：(1)超声波对反应有加速作用,产率也有相应的提高；用水作为反应溶剂优于其它反应溶剂；在原位产生亚铜离子的催化体系中醋酸铜优于其它二价铜盐；(2)在优化的实验条件下,合成了32个1,2,3-三氮唑类化合物,其中20个为新化合物,其结构经过IR, ESI MS, NMR的确认；(3)考查了超声波对反应选择性的影响,通过HMBC, COSY, NOE等2D NMR图谱对化合物的1,4-取代进行了确认。
2、以天然产物白杨素为母体,通过超声辅助下的Husigen-Click环加成反应将1,2,3-三氮唑药效团引入到白杨素的结构修饰中,对反应条件进行了优化。以硫酸铜／抗坏血酸钠为催化剂,叔丁醇／水等体积为溶剂,合成了14个新型的白杨素1,2,3-三氮唑衍生物,其结构经过IR, ESI MS, NMR等进行了确认,并对化合物的波谱特征进行了总结。
3、利用荧光光谱和紫外可见光谱法研究了5个白杨素1,2,3-三氮唑衍生物与牛血清蛋白、溶菌酶的相互作用。实验表明：白杨素1,2,3-三氮唑衍生物对蛋白的荧光有猝灭作用,且猝灭过程是由于形成了复合物而引起的静态猝灭；小分子与蛋白之间的作用力主要是静电和疏水作用力；白杨素的衍生物2-5-1与牛血清蛋白的结合常数比白杨素增强了5.5倍,说明1,2,3-三氮唑药效团的存在,增加了小分子与蛋白之间的相互作用。
N-heterocyclic drugs account for a large proportion of currently clinical used drugs and more than half of top 200 global pharmaceutical drugs contains the N-heterocyclic structure.1,2,3-triazoles, as a member of N-heterocycles, bear various biological activities such as anti-HIV, anti-microbial, anti-allergic, and selectiveβ3 adrenergic receptor agonist. Recently,1,2,3-triazole moiety, as an important pharmacophore, was widely introduced in to peptides, DNA, RNA and carbohydrates and so on. And the modifications showed good results. Chrysin, an important naturally occurring flavonoid, bears multiple biological activities, such as anti-viral, antibacterial, antioxidant, anticancer activities. However, the activity of chrysin decreased due to its poor absorption in the intestine. Copper(I)-catalyzed 1, 3-dipolar Huisgen cycloaddition (CuAAC) reaction of azides and terminal alkynes gained much attention because it is an mild, high yield, good regioselectivity method and greatly used in synthesis and structural modification of durgs.
In the work describe in this chapter 1, the recently development and applications of Huisgen-Click reaction, the structure modifications of chrysin were reviewed. In the following chapters,1,2,3-triazole moiety was firstly coupled with chrysin by an optimized ultrasound-assisted Huisgen-Click reaction and a series of chrysin derivatives linked with 1,2,3-trizaole moiety were synthesized. The non-covalent interaction between those chrysin derivatives and BSA was studied by fluorescence spectroscopy and UV absorption spectroscopy.
1、The reaction between propargyl phenyl ether and ethyl 2-azidoacetate was selected as a model reaction for investigating the influence of ultrasound on the rate and yield of cycloaddition with different catalysts, solvents, base and ligand. The reaction condition was optimized through a series of experiments. The results are as follows:(1) Ultrasound irradiation not only acceletates the cycloadditon rate but also improves the product yield. Water is the better solvent than other tested solvents. Cu(OAc)2 is better than other tested Cu(II) salts in the catalyst system where Cu(I) ion is generated in situ; (2) Thirty two 1,4-disubstituted triazole derivatives were synthesized under the optimized condition, twenty of which are new compounds. Their structures were confirmed by IR, ESI MS and NMR. (3) The influence of ultrasound on the regioselectivity of the reaction was studied. The structure of 1,4-disubstituted triazole derivative was confirmed by 2D NMR such as HMBC, COSY, NOE.
2、A series of chrysin derivatives linked with 1,2,3-triazoles were synthesized using the CuAAC reaction under optimized conditions. The 1,3-dipolar cycloaddition reaction can be successfully carried out using CuSO4/sodium ascorbate as the catalyst,t-BuOH-H2O (1:1 v/v) as the solvent under the help of ultrasound at room temperature. Structures of the novel 14 compounds were determined by NMR, ESI MS, IR and elemental analysis. All the 1H、13C chemical shifts of the compound were assigned using 2D NMR techniques, including DEPT、1H-1H COSY、13C-1H HSQC、13C-1H HMBC.
3、The interaction of five novel chrysin derivatives with Bovine Serum Albumin, Lysozyme were studied using fluorescence spectroscopy and UV absorption spectroscopy. The result showed that small molecules are able to couse fluorescent of proteins quench, and the quenching process is static quenching. Electrostatic and hydrophobic forces are mainly involved in the initial interaction. Binding constant between 2-5-1 and BSA is as 5.5 times as that between chrysin and BSA, which indicates that the introduced 1,2,3-triazole enhanced the interaction between the small molecules with BSA.
引文
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