bis[2-(2-hydroxyethoxy)ethylthio]maleonitrile

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: bis[2-(2-hydroxyethoxy)ethylthio]maleonitrile
• 英文别名: (Z)-2,3-bis[2-(2-hydroxyethoxy)ethylsulfanyl]but-2-enedinitrile
• 化学式: C₁₂H₁₈N₂O₄S₂
• 分子量: 318.418
• InChiKey: XBEDLRQTUTYWIU-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis[2-(2-hydroxyethoxy)ethylthio]maleonitrile 、 1-imino-4,7-bis(1-methylethoxy)-1H-isoindolin-3-amine 在 magnesium n-propoxide 、 三氟乙酸 作用下， 以 丙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 以8%的产率得到1,4,13,16-tetrakis(1-methylethoxy)-8,9,20,21-tetrakis[2-(2-hydroxyethoxy)ethylthio]-25H,27H-dibenzo[b,l]porphyrazine
  参考文献：
  名称：

  Charge Dependence of Cellular Uptake and Selective Antitumor Activity of Porphyrazines

  摘要：

  Porphyrazines (pzs), or tetraazaporphyrins, can be viewed as porphyrinic macrocycles in which the porphyrin meso (CH) groups are replaced by nitrogen atoms; as such, it can be anticipated that pzs would show similar biocompatibility and biodistribution to those of porphyrins. However, distinctive chemical and physical features of the pzs differentiate them from either the porphyrins or phthalocyanines, in particular making them excellent candidates as optical imaging/therapeutic agents. The novelty of the pzs requires that we first determine how specific structures selectively alter biological function, leading to the development of "rules" that will be used to predict future biologically functional pzs. In the first of these studies, we present here a correlation of pz charge with biocompatibility for a suite of three pzs-neutral, negative, and positive. Confocal fluorescence microscopy and proliferation/viability measurements disclose that the three pzs differ in their toxicity, uptake, and localization. in A549 human lung adenocarcinoma cells and WI-38 VA13 normal cells. Interestingly, the negatively charged pz exhibits selective dark toxicity in pulmonary adenocarcinoma cells.

  DOI：

  10.1021/jm050466y
• 作为产物：
  描述：

  2-氯乙氧基乙醇 、 disodium cis-1,2-dicyano-1,2-ethylenedithiolate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以55%的产率得到bis[2-(2-hydroxyethoxy)ethylthio]maleonitrile
  参考文献：
  名称：

  Charge Dependence of Cellular Uptake and Selective Antitumor Activity of Porphyrazines

  摘要：

  Porphyrazines (pzs), or tetraazaporphyrins, can be viewed as porphyrinic macrocycles in which the porphyrin meso (CH) groups are replaced by nitrogen atoms; as such, it can be anticipated that pzs would show similar biocompatibility and biodistribution to those of porphyrins. However, distinctive chemical and physical features of the pzs differentiate them from either the porphyrins or phthalocyanines, in particular making them excellent candidates as optical imaging/therapeutic agents. The novelty of the pzs requires that we first determine how specific structures selectively alter biological function, leading to the development of "rules" that will be used to predict future biologically functional pzs. In the first of these studies, we present here a correlation of pz charge with biocompatibility for a suite of three pzs-neutral, negative, and positive. Confocal fluorescence microscopy and proliferation/viability measurements disclose that the three pzs differ in their toxicity, uptake, and localization. in A549 human lung adenocarcinoma cells and WI-38 VA13 normal cells. Interestingly, the negatively charged pz exhibits selective dark toxicity in pulmonary adenocarcinoma cells.

  DOI：

  10.1021/jm050466y

文献信息

• Charge Dependence of Cellular Uptake and Selective Antitumor Activity of Porphyrazines
  作者：Neal D. Hammer、Sangwan Lee、Benjamin J. Vesper、Kim M. Elseth、Brian M. Hoffman、Anthony G. M. Barrett、James A. Radosevich

  DOI：10.1021/jm050466y

  日期：2005.12.1

  Porphyrazines (pzs), or tetraazaporphyrins, can be viewed as porphyrinic macrocycles in which the porphyrin meso (CH) groups are replaced by nitrogen atoms; as such, it can be anticipated that pzs would show similar biocompatibility and biodistribution to those of porphyrins. However, distinctive chemical and physical features of the pzs differentiate them from either the porphyrins or phthalocyanines, in particular making them excellent candidates as optical imaging/therapeutic agents. The novelty of the pzs requires that we first determine how specific structures selectively alter biological function, leading to the development of "rules" that will be used to predict future biologically functional pzs. In the first of these studies, we present here a correlation of pz charge with biocompatibility for a suite of three pzs-neutral, negative, and positive. Confocal fluorescence microscopy and proliferation/viability measurements disclose that the three pzs differ in their toxicity, uptake, and localization. in A549 human lung adenocarcinoma cells and WI-38 VA13 normal cells. Interestingly, the negatively charged pz exhibits selective dark toxicity in pulmonary adenocarcinoma cells.