(E)-2-((E)-1-(2-isonicotinoylhydrazono)ethyl)phenyl 3-(2,4-dihydroxyphenyl)acrylate | 1801141-38-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-((E)-1-(2-isonicotinoylhydrazono)ethyl)phenyl 3-(2,4-dihydroxyphenyl)acrylate
• 英文别名: [2-[(E)-C-methyl-N-(pyridine-4-carbonylamino)carbonimidoyl]phenyl] (E)-3-(2,4-dihydroxyphenyl)prop-2-enoate
• CAS: 1801141-38-7
• 化学式: C₂₃H₁₉N₃O₅
• 分子量: 417.421
• InChiKey: JQXCSMVKBUFDOV-DGCPBWIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (E)-3-(2,4-二羟基苯基)丙烯酸乙酯 在 吡啶 、 四(三苯基膦)钯 、 苯硅烷 、 potassium carbonate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.0h， 生成 (E)-2-((E)-1-(2-isonicotinoylhydrazono)ethyl)phenyl 3-(2,4-dihydroxyphenyl)acrylate
  参考文献：
  名称：

  A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress

  摘要：

  UVA radiation can damage cells and tissues by direct photodamage of biomolecules as well as by initiating metal-catalyzed oxidative stress. In order to alleviate both concerns simultaneously, we synthesized a multifunctional prochelator PC-HAPI (2-((E)-1-(2-isonicotinoylhydrazono) ethyl)phenyl(trans)-3-(2,4-dihydroxyphenyl)acrylate) that contains a trans-(o-hydroxy)cinnamate ester photocleavable protecting group that is cleaved upon UVA exposure to release a coumarin, umbelliferone, and an aroylhydrazone metal chelator, HAPI (N'-[1-(2-hydroxyphenyl)ethyliden]isonicotinoylhydrazide). While the prochelator PC-HAPI exhibits negligible affinity for iron, it responds rapidly to UVA irradiation and converts to an iron-binding chelator that inhibits iron-catalyzed formation of reactive oxygen species and protects cells from UVA damage. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.048

文献信息

• A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress
  作者：Andrew T. Franks、Qin Wang、Katherine J. Franz

  DOI：10.1016/j.bmcl.2015.06.048

  日期：2015.11

  UVA radiation can damage cells and tissues by direct photodamage of biomolecules as well as by initiating metal-catalyzed oxidative stress. In order to alleviate both concerns simultaneously, we synthesized a multifunctional prochelator PC-HAPI (2-((E)-1-(2-isonicotinoylhydrazono) ethyl)phenyl(trans)-3-(2,4-dihydroxyphenyl)acrylate) that contains a trans-(o-hydroxy)cinnamate ester photocleavable protecting group that is cleaved upon UVA exposure to release a coumarin, umbelliferone, and an aroylhydrazone metal chelator, HAPI (N'-[1-(2-hydroxyphenyl)ethyliden]isonicotinoylhydrazide). While the prochelator PC-HAPI exhibits negligible affinity for iron, it responds rapidly to UVA irradiation and converts to an iron-binding chelator that inhibits iron-catalyzed formation of reactive oxygen species and protects cells from UVA damage. (C) 2015 Elsevier Ltd. All rights reserved.