三种2-羟基-1-萘醛酰腙的晶体结构、热分解及其与CT-DNA的相互作用

引用本文: 赵顺省, 李兰兰, 刘向荣, 丁作成, 杨再文. 三种2-羟基-1-萘醛酰腙的晶体结构、热分解及其与CT-DNA的相互作用[J]. 物理化学学报, 2017, 33(2): 356-363. doi: 10.3866/PKU.WHXB201610191 shu

Citation: ZHAO Shun-Sheng, LI Lan-Lan, LIU Xiang-Rong, DING Zuo-Cheng, YANG Zai-Wen. Crystal Structure, Thermal Decomposition and Interaction with CT-DNA of Three 2-Hydroxy-1-naphthaldehyde Acyl Hydrazones[J]. Acta Physico-Chimica Sinica, 2017, 33(2): 356-363. doi: 10.3866/PKU.WHXB201610191 shu

三种2-羟基-1-萘醛酰腙的晶体结构、热分解及其与CT-DNA的相互作用

西安科技大学化学与化工学院, 西安 710054
基金项目:
国家自然科学基金（21103135，21073139，21301139），陕西省自然科学基础研究计划（2016JM2011）及陕西省教育厅自然科学专项（15JK1492）资助项目

摘要: 合成了2-羟基萘醛苯乙酰腙（1）、2-羟基萘醛-4-羟基苯乙酰腙（2）和2-羟基萘醛-2-甲氧基苯乙酰腙（3）三种新型酰腙化合物，通过单晶X射线衍射（XRD）、元素分析和傅里叶变换红外（FTIR）光谱对化合物结构进行了表征。单晶X射线衍射结果表明，化合物2和3结晶为单斜晶系，空间群C2/c。而化合物1结晶为正交晶系，空间群为Pbca。热重（TG）分析结果表明，化合物1、2、3分子骨架热分解的温度分别为318.23、319.04、323.01℃，对应的热分解过程表观活化能分别为115.90、145.18、129.38 kJ·mol^-1。微量热研究表明，三种酰腙及其前驱体酰肼与小牛胸腺脱氧核糖核酸（CT-DNA）相互作用均为吸热作用，但作用时间（1.00-50.0 min）和反应熵变（0.47-15.50 kJ·mol^-1）有较大的差异。化合物1和2与CT-DNA的反应焓变均大于其前驱体酰肼a和b与CT-DNA的反应焓变，而化合物3与CT-DNA的反应焓变却小于其前驱体酰肼c与CT-DNA的反应焓变。

关键词:

酰腙
/ 晶体结构
/ 热重
/ 微量热
/ DNA作用

English

Crystal Structure, Thermal Decomposition and Interaction with CT-DNA of Three 2-Hydroxy-1-naphthaldehyde Acyl Hydrazones

College of Chemistry and Chemical Engineering, Xi′an University of Science and Technology, Xi′an 710054, P. R. China
Received Date: 05 September 2016
Revised Date: 19 October 2016
Fund Project:
The project was supported by the National Natural Science Foundation of China (21103135, 21073139, 21301139), Natural Science Basic Research Plan in Shaanxi Province, China (2016JM2011), and Scientific Research Program Funded by Shaanxi Provincial Education Commission, China (15JK1492).

Abstract: Three acyl hydrazones N'-((2-hydroxynaphthalen-1-yl)methylene)-2-phenylacetohydrazide (1), N'-((2-hydroxynaphthalen-1-yl) methylene)-2-(4-hydroxyphenyl)acetohydrazide hydrate (2), and N'-((2-hydroxynaphthalen-1-yl) methylene)-2-(2-methoxyphenyl) acetohydrazide hydrate (3) were synthesized and then characterized by elemental analysis and single-crystal X-ray diffraction. The crystallographic data indicated that both compounds 2 and 3 crystallized in the monoclinic crystal lattice, space group C2/c, while compound 1 crystallized in the orthorhombic space group Pbca. The thermal decomposition processes of the three hydrazones were studied by thermogravimetry. The thermal decomposition temperatures of compounds 1, 2, and 3 were 318.23, 319.04, and 323.01℃, respectively. Meanwhile, the apparent activation energies for thermal decomposition for compounds 1, 2, and 3 were 115.90, 145.18, and 129.38 kJ·mol^-1, respectively, calculated according to the Kissinger and Ozawa equations. The interactions of compounds 1-3 with calf thymus (CT)-DNA were evaluated by microcalorimetry. The results indicated these interactions were homogenous endothermic processes with non-identical interaction time (1.00-50.0 min) and interaction enthalpies (0.47-15.50 kJ·mol^-1). The interaction enthalpies of compounds 1 and 2 were higher than those of their precursors, while the interaction enthalpy of compound 3 was lower than that of its precursor.

Key words:

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沈阳化工大学材料科学与工程学院沈阳 110142

三种2-羟基-1-萘醛酰腙的晶体结构、热分解及其与CT-DNA的相互作用

English

Crystal Structure, Thermal Decomposition and Interaction with CT-DNA of Three 2-Hydroxy-1-naphthaldehyde Acyl Hydrazones

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

三种2-羟基-1-萘醛酰腙的晶体结构、热分解及其与CT-DNA的相互作用

English

Crystal Structure, Thermal Decomposition and Interaction with CT-DNA of Three 2-Hydroxy-1-naphthaldehyde Acyl Hydrazones

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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