4-[4-[(2-Methylquinolin-8-yl)sulfamoyl]anilino]-4-oxobutanoic acid | 1173881-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-[4-[(2-Methylquinolin-8-yl)sulfamoyl]anilino]-4-oxobutanoic acid
• 英文别名: 4-[4-[(2-methylquinolin-8-yl)sulfamoyl]anilino]-4-oxobutanoic acid
• CAS: 1173881-89-4
• 化学式: C₂₀H₁₉N₃O₅S
• 分子量: 413.454
• InChiKey: UOUZSYNINVHRGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[4-[(2-Methylquinolin-8-yl)sulfamoyl]anilino]-4-oxobutanoic acid 、 单-6-O-氨基-Β-环糊精 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 57.0h， 以25%的产率得到
  参考文献：
  名称：

  Convenient and highly effective fluorescence sensing for Hg2+ in aqueous solution and thin film

  摘要：

  A quinolinocyclodextrin, that is, MQAS-beta-cyclodextrin (MQAS = N-(2-methyl-8-amino-quinolyl)-p-aminobenzene sulfonamide) was synthesized. Further experiments showed that it could form very stable stoichiometric 2:1 complex with Zn2+ in water. Significantly, the resultant quinolinocyclodextrin/Zn2+ complex showed the specific fluorescence response to Hg2+ over other metal ions, which could be readily distinguished in either aqueous solution or the PVA-based thin film. This finding would enable Zn center dot 3(2) complex as a convenient and highly efficient fluorescence sensor for the detection of Hg2+. (E) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.018
• 作为产物：
  描述：

  丁二酸酐 、 4-amino-N-(2-methylquinolin-8-yl)benzenesulfonamide 以 甲苯 为溶剂， 反应 5.0h， 以61%的产率得到4-[4-[(2-Methylquinolin-8-yl)sulfamoyl]anilino]-4-oxobutanoic acid
  参考文献：
  名称：

  Convenient and highly effective fluorescence sensing for Hg2+ in aqueous solution and thin film

  摘要：

  A quinolinocyclodextrin, that is, MQAS-beta-cyclodextrin (MQAS = N-(2-methyl-8-amino-quinolyl)-p-aminobenzene sulfonamide) was synthesized. Further experiments showed that it could form very stable stoichiometric 2:1 complex with Zn2+ in water. Significantly, the resultant quinolinocyclodextrin/Zn2+ complex showed the specific fluorescence response to Hg2+ over other metal ions, which could be readily distinguished in either aqueous solution or the PVA-based thin film. This finding would enable Zn center dot 3(2) complex as a convenient and highly efficient fluorescence sensor for the detection of Hg2+. (E) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.018

文献信息

• Construction and transmembrane dissociation behavior of supramolecular assembly of quinolinocyclodextrin with porphyrin
  作者：Miao Yu、Yong Chen、Ning Zhang、Yu Liu

  DOI：10.1039/c0ob00080a

  日期：——

  Through the stoichiometric 2 : 1 coordination of Zn2+ with 4-amino-N-(2-methylquinolin-8-yl)benzenesulfonamide-modified per-methyl-β-cyclodextrin (MQAS-PMCD) and the strong inclusion complexation of permethyl-β-cyclodextrin cavity with meso-tetrakis-(4-sulfonatophenyl)-porphyrin (TSPP), an environment-sensitive Zn2+/cyclodextrin/porphyrin triad supramolecular assembly was constructed, and its structure was fully characterized by UV/vis spectroscopy, fluorescence spectroscopy, powder X-ray diffraction (XRD), scanning tunneling microscopy (STM) and transmission electron microscopy (TEM). Fluorescence spectrometric studies showed that this supramolecular assembly was stable and barely emitted green fluorescence in water due to the energy transfer process, but gave the strong green fluorescence when changing to a hydrophobic environment due to the disruption of the assembly. Further studies on the cell staining experiments by means of fluorescence microscopy showed that this supramolecular assembly was disrupted to release the MQAS-PMCD/Zn2+ and porphyrin components when interacting with the cell membrane. Subsequently, the released MQAS-PMCD/Zn2+ complex remained in the cell membrane, while the porphyrin component entered the cells. This transmembrane dissociation property of the supramolecular assembly will enable its application in the delivery of biological and drug molecules containing the anionic porphyrin skeleton such as β-octaphenyl-meso-tetra(4-carboxyl)-phenylporphyrin and so on.

  通过 Zn2+ 与 4-氨基-N-（2-甲基喹啉-8-基）苯磺酰胺修饰的全甲基-β-环糊精（MQAS-PMCD）的 2 ：通过Zn2+与4-氨基-N-(2-甲基喹啉-8-基)苯磺酰胺修饰的过甲基-β-环糊精（MQAS-PMCD）的2 : 1配位，以及过甲基-β-环糊精空腔与中-四-(4-磺酸基苯基)-卟啉（TSPP）的强包合络合、通过紫外/可见光谱、荧光光谱、粉末 X 射线衍射（XRD）、扫描隧道显微镜（STM）和透射电子显微镜（TEM）对其结构进行了全面表征。荧光光谱研究表明，这种超分子组装体是稳定的，在水中由于能量转移过程几乎不发出绿色荧光，但当换到疏水环境中时，由于组装体被破坏而发出强烈的绿色荧光。通过荧光显微镜对细胞染色实验的进一步研究表明，这种超分子组装在与细胞膜相互作用时被破坏，释放出 MQAS-PMCD/Zn2+ 和卟啉成分。随后，释放的 MQAS-PMCD/Zn2+ 复合物留在细胞膜上，而卟啉成分则进入细胞。超分子组装体的这种跨膜解离特性将使其能够应用于含有阴离子卟啉骨架的生物和药物分子的递送，如β-辛基苯基-中性-四（4-羧基）-苯基卟啉等。
• Convenient and highly effective fluorescence sensing for Hg2+ in aqueous solution and thin film
  作者：Yu Liu、Miao Yu、Yong Chen、Ning Zhang

  DOI：10.1016/j.bmc.2009.04.018

  日期：2009.6

  A quinolinocyclodextrin, that is, MQAS-beta-cyclodextrin (MQAS = N-(2-methyl-8-amino-quinolyl)-p-aminobenzene sulfonamide) was synthesized. Further experiments showed that it could form very stable stoichiometric 2:1 complex with Zn2+ in water. Significantly, the resultant quinolinocyclodextrin/Zn2+ complex showed the specific fluorescence response to Hg2+ over other metal ions, which could be readily distinguished in either aqueous solution or the PVA-based thin film. This finding would enable Zn center dot 3(2) complex as a convenient and highly efficient fluorescence sensor for the detection of Hg2+. (E) 2009 Elsevier Ltd. All rights reserved.