分子间作用力构筑的具有柔性结构的醋氯芬酸多聚物: 晶体结构, 热稳定性, 溶解度和DFT计算

doi:10.3866/PKU.WHXB201412231

物理化学学报 >> 2015, Vol. 31 >> Issue (2): 211-220.doi: 10.3866/PKU.WHXB201412231

分子间作用力构筑的具有柔性结构的醋氯芬酸多聚物: 晶体结构, 热稳定性, 溶解度和DFT计算

孙盼盼¹, 刘翔宇^1,2, 孙琳², 张盛¹, 魏青¹, 尹琰¹, 杨奇¹, 陈三平¹

1. 西北大学化学与材料科学学院, 合成与天然功能分子化学教育部重点实验室, 西安 710069;
2. 宁夏大学化学化工学院, 银川 750021

收稿日期:2014-10-30 修回日期:2014-12-22 发布日期:2015-01-26
通讯作者: 陈三平, 魏青 E-mail:sanpingchen@126.com,sanpingchen312@gmail.com;weiqq@126.com
基金资助:
国家自然科学基金(21373162, 21463020, 21073142, 21173168)和陕西自然科学基金(11JS110, 2013JM2002, SJ08B09)资助项目

Intermolecular Interaction Induced Multi-Polymers of Aceclofenac with Flexible Conformation: Crystal Structure, Thermostability, Solubility and DFT Calculations

SUN Pan-Pan¹, LIU Xiang-Yu^1,2, SUN Lin², ZHANG Sheng¹, WEI Qing¹, YIN Yan¹, YANG Qi¹, CHEN San-Ping¹

1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710069, P. R. China;
2. School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021, P. R. China

Received:2014-10-30 Revised:2014-12-22 Published:2015-01-26
Contact: CHEN San-Ping, WEI Qing E-mail:sanpingchen@126.com,sanpingchen312@gmail.com;weiqq@126.com
Supported by:
The project was supported by the National Natural Science Foundation of China (21373162, 21463020, 21073142, 21173168) and Natural Science Foundation of Shaanxi Province, China (11JS110, 2013JM2002, SJ08B09).

摘要/Abstract

摘要：

非甾体类抗炎药物醋氯芬酸(ACF)的水溶性差, 导致其生物利用度较低. 本文制备了三种多聚物, 分别是醋氯芬酸与4,4'-联吡啶(BIPY)共晶(1), 与3-氨基苯甲酸(3-ABA)盐(2)和与二甲基亚砜(DMSO)的溶剂化物(3), 利用红外光谱、粉末X射线衍射和单晶X射线衍射对它们的结构进行了表征. 结果表明, 化合物1-3的超分子结构是通过氢键、C―H…π和π…π堆积作用构筑而成, 三个多聚物具有良好的热稳定性. 从热力学角度分析和密度泛函理论(DFT)计算说明ACF在化合物3中的构象比其在化合物1和2中更稳定. 此外, ACF形成共晶、盐和溶剂化物后有效提高了其溶解度.

关键词: 醋氯芬酸, 多聚物, 热稳定性, 密度泛函理论, 溶解度

Abstract:

The non-steroidal anti-inflammatory drug aceclofenac (ACF) has low bioavailability because of its poor water solubility. To enhance its water solubility we synthesized three compounds: a co-crystal of ACF- 0.5BIPY (4,4'-bipyridine) (1), a salt of ACF-3-ABA (3-aminobenzoic acid) (2), and a solvate of ACF-DMSO (dimethyl sulfoxide) (3). These compounds were characterized by infrared spectroscopy, powder and single crystal X-ray diffractions. The supramolecular structures of 1-3 are sustained by hydrogen bonding C―H…π and π…π stacking interactions and they have favorable thermal stabilities. Thermodynamically, DFT calculations revealed that the most stable conformation of ACF exists in compound 3 and this structure is more stable than 1 and 2. Furthermore, upon the formations of the co-crystal, the salt or the solvate the solubility of ACF improves significantly.

Key words: Aceclofenac, Multi-polymer, Thermostability, Density functional theory, Solubility

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孙盼盼, 刘翔宇, 孙琳, 张盛, 魏青, 尹琰, 杨奇, 陈三平. 分子间作用力构筑的具有柔性结构的醋氯芬酸多聚物: 晶体结构, 热稳定性, 溶解度和DFT计算[J]. 物理化学学报, 2015, 31(2), 211-220. doi: 10.3866/PKU.WHXB201412231

SUN Pan-Pan, LIU Xiang-Yu, SUN Lin, ZHANG Sheng, WEI Qing, YIN Yan, YANG Qi, CHEN San-Ping. Intermolecular Interaction Induced Multi-Polymers of Aceclofenac with Flexible Conformation: Crystal Structure, Thermostability, Solubility and DFT Calculations[J]. Acta Phys. -Chim. Sin. 2015, 31(2), 211-220. doi: 10.3866/PKU.WHXB201412231

链接本文: https://www.whxb.pku.edu.cn/CN/10.3866/PKU.WHXB201412231

https://www.whxb.pku.edu.cn/CN/Y2015/V31/I2/211

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分子间作用力构筑的具有柔性结构的醋氯芬酸多聚物: 晶体结构, 热稳定性, 溶解度和DFT计算

Intermolecular Interaction Induced Multi-Polymers of Aceclofenac with Flexible Conformation: Crystal Structure, Thermostability, Solubility and DFT Calculations

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