3-(3-(4-(di-2,5,8,11-tetraoxatridecan-13-ylamino)phenyl)acryloyl)-7-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2H-chromen-2-one | 1404191-71-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(3-(4-(di-2,5,8,11-tetraoxatridecan-13-ylamino)phenyl)acryloyl)-7-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2H-chromen-2-one
• 英文别名: 3-[3-[4-[bis[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethyl]amino]phenyl]prop-2-enoyl]-7-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]chromen-2-one
• CAS: 1404191-71-4
• 化学式: C₄₃H₆₃NO₁₅
• 分子量: 833.971
• InChiKey: HCYFPCPSISGHMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  59
• 可旋转键数：
  38
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  3-乙酰基-7-羟基-苯并吡喃-2-酮 在 哌啶 、 溶剂黄146 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正丁醇 为溶剂， 反应 28.0h， 生成 3-(3-(4-(di-2,5,8,11-tetraoxatridecan-13-ylamino)phenyl)acryloyl)-7-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and in Vitro Photocytotoxicity of Coumarin Derivatives for One- and Two-Photon Excited Photodynamic Therapy

  摘要：

  Triethylene glycol functionalized coumarin derivatives 1-5 were synthesized and investigated as photosensitizers for one- and two-photon excited photodynamic therapy (PDT). Their absorption, fluorescence, triplet-state quantum yields, and singlet oxygen quantum yields were found to be significantly related to the substituent at the 7-position of the coumarin ring. In vitro photocytotoxicity of these derivatives toward HepG2 cells was examined and compared with a clinical drug. In vitro generation of reactive oxygen species (ROS), cellular uptake, and intracellular distribution of these derivatives were also characterized to fully reveal their structure-property relationships. The results showed that derivative 5, with a two-photon absorption cross section value of 1556 GM, could be a powerful PDT agent for both superficial diseases and solid tumors.

  DOI：

  10.1021/jm400025g

文献信息

• Synthesis and in Vitro Photocytotoxicity of Coumarin Derivatives for One- and Two-Photon Excited Photodynamic Therapy
  作者：Qianli Zou、Yanyan Fang、Yuxia Zhao、Hongyou Zhao、Ying Wang、Ying Gu、Feipeng Wu

  DOI：10.1021/jm400025g

  日期：2013.7.11

  Triethylene glycol functionalized coumarin derivatives 1-5 were synthesized and investigated as photosensitizers for one- and two-photon excited photodynamic therapy (PDT). Their absorption, fluorescence, triplet-state quantum yields, and singlet oxygen quantum yields were found to be significantly related to the substituent at the 7-position of the coumarin ring. In vitro photocytotoxicity of these derivatives toward HepG2 cells was examined and compared with a clinical drug. In vitro generation of reactive oxygen species (ROS), cellular uptake, and intracellular distribution of these derivatives were also characterized to fully reveal their structure-property relationships. The results showed that derivative 5, with a two-photon absorption cross section value of 1556 GM, could be a powerful PDT agent for both superficial diseases and solid tumors.