三唑联噻二唑系列杂环化合物的合成表征、量化计算及性质的研究
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摘要
本文利用活性亚结构拼接和生物电子等排原理,将不同作用机制的活性基团1,2,4-三唑和1,3,4-噻二唑引入到目标化合物中,共设计合成了五种结构类型、31个新型的三唑联噻二唑类化合物,得到4个目标化合物的单晶。其结构类型如下:
通过1HNMR、IR、EA和X射线单晶衍射分析进行了结构表征,并对其理化性质、谱学性质、合成方法进行了分析讨论。
运用量子化学密度泛函方法,在B3LYP/6-3lG*水平上对目标化合物的分子结构进行几何构型全优化及频率计算,得到了目标化合物的三维稳定构型;计算了分子中各原子的净电荷分布、轨道能、轨道跃迁能、偶极距、红外光谱和热力学函数,并从理论上进行了分析讨论。理论计算的红外光谱图与实验结果一致。采用电化学阻抗方法、极化曲线法和失重法,研究了3种目标化合物B2、B3和B4对碳钢在盐酸介质中的缓蚀作用;根据吸附理论和热力学方程讨论了缓蚀剂在金属表面的吸附机理,计算了相关的吸附平衡常数Kads、标准吸附焓0ΔH ads、标准吸附自由能ΔG a0ds和标准吸附熵ΔSa0ds;用量子化学密度泛函理论和统计方法研究了目标化合物的缓蚀效率与其结构的关系。结果表明,B2、B3和B4都对盐酸介质中的碳钢有缓蚀作用,B4的缓蚀效率最高。同一温度下,缓蚀效率随着缓蚀剂浓度的增大而增大;缓蚀剂浓度相同时,对碳钢的缓蚀效率随温度的升高而增大;缓蚀剂在金属表面的吸附类型为化学吸附,抑制腐蚀是通过分子中的电子,尤其是分子中氮原子上的电子转移到金属表面形成配位键而被吸附,从而阻止氢离子对金属的腐蚀,产生缓蚀作用。
采用MTT方法对合成的A、B两个系列化合物进行了抗癌活性筛选,结果表明,化合物A1、A3、A6、A7、A8和B2对乳腺癌细胞4T-1增殖有明显的抑制作用;化合物A2和A9对肝癌细胞株7402增殖具有明显的抑制作用。
Thirty-one novel triazoles connecting thiadiazole compounds with five types of structure were designed and synthesized by introducing different active groups into the target compounds, according to putting together the active sub-structure and the rule of bioisosterism, which are summarized as follows:
All title compounds have been characterized by IR, 1HMR, EA and crystal structure determination,respectively. The Physiochemical Properties and spectroscopy of these compounds were systematically investigated, and reaction conditions have also been discussed.
Full geometry optimizations and frequency calculations for all the series of molecules have been carried out by using quantum chemical density functional theory method at B3LYP/6-31G* level. The pure charge distributions of every atom, EHOMO, ELUMO, DELH,μ, IR spectrum and thermodynamic parameters of title compounds were obtained and discussed in theory. The results indicated that IR spectrum calculated could be well confirmed by the experimental data.
Corrosion inhibition behavior of compounds B2, B3 and B4 to carbon steel in 1M HCl solution were studied by electrochemical impedance, the polarization curves and weight loss method. Adsorption mechanism of inhibitor in the metal surface was discussed by adsorption theory and thermodynamic equations, and, adsorption equilibrium constants Kads, standards adsorption enthalpy (ΔHa0ds), standard absorption free energy (ΔG a0ds) and standard adsorption entropy (ΔS a0ds) were obtained. The relationship between corrosion inhibition efficiency and the structure of title compounds were studied by quantum chemical density functional theory and statistical methods. The results showed that B2, B3 and B4 can inhibit corrosion of carbon steel, especially B4. Corrosion inhibition efficiency was increased with the increase of inhibitor concentration at same temperature, and also increased with the increase of temperature at the same concentration of inhibitor. The adsorption of B2, B3 and B4 in metal surface was chemical adsorption, which generated by electron of nitrogen atoms transferring to the metal surface and formed coordination bond, so it can inhibit corrosion of carbon steel in 1M HCl solution.
Antitumor activities of some new compounds were tested by MTT method. The results showed that compounds A1, A3, A6, A7, A8 and B2 effectively have inhibitory function to breast cancer cell, and compounds A2 and A9 effectively have inhibitory function to hepatoma cell.
通过1HNMR、IR、EA和X射线单晶衍射分析进行了结构表征,并对其理化性质、谱学性质、合成方法进行了分析讨论。
运用量子化学密度泛函方法,在B3LYP/6-3lG*水平上对目标化合物的分子结构进行几何构型全优化及频率计算,得到了目标化合物的三维稳定构型;计算了分子中各原子的净电荷分布、轨道能、轨道跃迁能、偶极距、红外光谱和热力学函数,并从理论上进行了分析讨论。理论计算的红外光谱图与实验结果一致。采用电化学阻抗方法、极化曲线法和失重法,研究了3种目标化合物B2、B3和B4对碳钢在盐酸介质中的缓蚀作用;根据吸附理论和热力学方程讨论了缓蚀剂在金属表面的吸附机理,计算了相关的吸附平衡常数Kads、标准吸附焓0ΔH ads、标准吸附自由能ΔG a0ds和标准吸附熵ΔSa0ds;用量子化学密度泛函理论和统计方法研究了目标化合物的缓蚀效率与其结构的关系。结果表明,B2、B3和B4都对盐酸介质中的碳钢有缓蚀作用,B4的缓蚀效率最高。同一温度下,缓蚀效率随着缓蚀剂浓度的增大而增大;缓蚀剂浓度相同时,对碳钢的缓蚀效率随温度的升高而增大;缓蚀剂在金属表面的吸附类型为化学吸附,抑制腐蚀是通过分子中的电子,尤其是分子中氮原子上的电子转移到金属表面形成配位键而被吸附,从而阻止氢离子对金属的腐蚀,产生缓蚀作用。
采用MTT方法对合成的A、B两个系列化合物进行了抗癌活性筛选,结果表明,化合物A1、A3、A6、A7、A8和B2对乳腺癌细胞4T-1增殖有明显的抑制作用;化合物A2和A9对肝癌细胞株7402增殖具有明显的抑制作用。
Thirty-one novel triazoles connecting thiadiazole compounds with five types of structure were designed and synthesized by introducing different active groups into the target compounds, according to putting together the active sub-structure and the rule of bioisosterism, which are summarized as follows:
All title compounds have been characterized by IR, 1HMR, EA and crystal structure determination,respectively. The Physiochemical Properties and spectroscopy of these compounds were systematically investigated, and reaction conditions have also been discussed.
Full geometry optimizations and frequency calculations for all the series of molecules have been carried out by using quantum chemical density functional theory method at B3LYP/6-31G* level. The pure charge distributions of every atom, EHOMO, ELUMO, DELH,μ, IR spectrum and thermodynamic parameters of title compounds were obtained and discussed in theory. The results indicated that IR spectrum calculated could be well confirmed by the experimental data.
Corrosion inhibition behavior of compounds B2, B3 and B4 to carbon steel in 1M HCl solution were studied by electrochemical impedance, the polarization curves and weight loss method. Adsorption mechanism of inhibitor in the metal surface was discussed by adsorption theory and thermodynamic equations, and, adsorption equilibrium constants Kads, standards adsorption enthalpy (ΔHa0ds), standard absorption free energy (ΔG a0ds) and standard adsorption entropy (ΔS a0ds) were obtained. The relationship between corrosion inhibition efficiency and the structure of title compounds were studied by quantum chemical density functional theory and statistical methods. The results showed that B2, B3 and B4 can inhibit corrosion of carbon steel, especially B4. Corrosion inhibition efficiency was increased with the increase of inhibitor concentration at same temperature, and also increased with the increase of temperature at the same concentration of inhibitor. The adsorption of B2, B3 and B4 in metal surface was chemical adsorption, which generated by electron of nitrogen atoms transferring to the metal surface and formed coordination bond, so it can inhibit corrosion of carbon steel in 1M HCl solution.
Antitumor activities of some new compounds were tested by MTT method. The results showed that compounds A1, A3, A6, A7, A8 and B2 effectively have inhibitory function to breast cancer cell, and compounds A2 and A9 effectively have inhibitory function to hepatoma cell.
引文
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