3-[4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzyl]-1,7-dimethylxanthine | 939438-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3-[4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzyl]-1,7-dimethylxanthine
• CAS: 939438-96-7
• 化学式: C₂₂H₂₅N₅O₁₀
• 分子量: 519.468
• InChiKey: OPPLHGMDAMPJCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  176.02
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3-[4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzyl]-1,7-dimethylxanthine 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 3-[4,5-bis(acetoxymethoxycarbonylmethoxy)-2-nitrobenzyl]-1,7-dimethylxanthine
  参考文献：
  名称：

  Photochemical Gating of Intracellular Ca²⁺ Release Channels

  摘要：

  We have synthesized BiNiX, a caged methylxanthine agonist for the ryanodine receptor (RyR)the major calcium channel that mediates Ca2+ release from intracellular Ca2+ stores in electrically excitable cells. BiNiX is easily loaded into living cells through incubation with its acetoxymethyl (AM) ester. Delivery of focused UV light pulses to the loaded cell releases paraxanthine focally and rapidly to activate RyRs to release Ca2+, thus elevating intracellular Ca2+ concentration to initiate Ca2+-dependent signaling cascades. We demonstrate the biological utility of BiNiX in heart muscle cells by showing that local intracellular photolysis of BiNiX triggers Ca2+ release and consequent muscle contraction.

  DOI：

  10.1021/ja069361q
• 作为产物：
  描述：

  4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzyl alcohol 在 四丁基硫酸氢铵 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 3-[4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzyl]-1,7-dimethylxanthine
  参考文献：
  名称：

  Photochemical Gating of Intracellular Ca²⁺ Release Channels

  摘要：

  We have synthesized BiNiX, a caged methylxanthine agonist for the ryanodine receptor (RyR)the major calcium channel that mediates Ca2+ release from intracellular Ca2+ stores in electrically excitable cells. BiNiX is easily loaded into living cells through incubation with its acetoxymethyl (AM) ester. Delivery of focused UV light pulses to the loaded cell releases paraxanthine focally and rapidly to activate RyRs to release Ca2+, thus elevating intracellular Ca2+ concentration to initiate Ca2+-dependent signaling cascades. We demonstrate the biological utility of BiNiX in heart muscle cells by showing that local intracellular photolysis of BiNiX triggers Ca2+ release and consequent muscle contraction.

  DOI：

  10.1021/ja069361q