N-(amino(((9Z,11R,11aR)-5-(((4-methoxyphenyl)sulfonyl)imino)-3-oxo-5,6,7,8,11,11a-hexahydro-1H,3H-oxazolo[3,4-c][1,3]diazonin-11-yl)amino)methylene)-4-methoxybenzenesulfonamide | 1187038-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(amino(((9Z,11R,11aR)-5-(((4-methoxyphenyl)sulfonyl)imino)-3-oxo-5,6,7,8,11,11a-hexahydro-1H,3H-oxazolo[3,4-c][1,3]diazonin-11-yl)amino)methylene)-4-methoxybenzenesulfonamide
• CAS: 1187038-43-2
• 化学式: C₂₄H₂₈N₆O₈S₂
• 分子量: 592.654
• InChiKey: DLNOVIVREPXSKH-RWJYPNEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  191.08
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-(amino(((9Z,11R,11aR)-5-(((4-methoxyphenyl)sulfonyl)imino)-3-oxo-5,6,7,8,11,11a-hexahydro-1H,3H-oxazolo[3,4-c][1,3]diazonin-11-yl)amino)methylene)-4-methoxybenzenesulfonamide 在 oxone 、 osmium (III) chloride 、 sodium carbonate 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 48.0h， 以44%的产率得到N-(amino(((9S,9aR,10S,10aR)-9,9a-dihydroxy-5-(((4-methoxyphenyl)sulfonyl)imino)-3-oxohexahydro-1H,3H,5H-oxazolo[3,4-c]pyrrolo[2,1-f]pyrimidin-10-yl)amino)methylene)-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  De Novo Synthesis of Modified Saxitoxins for Sodium Ion Channel Study

  摘要：

  Access to novel forms of (+)-saxitoxin (STX), a potent and selective inhibitor of voltage-gated Na+ ion channels, has been made possible through de novo synthesis. Saxitoxin is believed to lodge in the outer mouth of the channel pore, thereby stoppering ion flux. Herein, we demonstrate that modification of the C13-carbamoyl unit can be accommodated in the binding site of the protein without significantly reducing ligand-receptor affinity. These discoveries have emboldened efforts to prepare photoaffinity-labeled and other unique forms of STX as pharmacological tools for interrogating both the molecular architecture and function of Na+ channels. A synthetic plan that makes such compounds generally available is described.

  DOI：

  10.1021/ja904179f
• 作为产物：
  描述：

  ((4R,5R,6Z)-5-(2-((4-methoxyphenyl)sulfonyl)guanidino)-2-(((4-methoxyphenyl)sulfonyl)imino)-2,3,4,5,8,9-hexahydro-1H-1,3-diazonin-4-yl)methyl (2,2,2-trichloroethyl) carbonate 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以86%的产率得到N-(amino(((9Z,11R,11aR)-5-(((4-methoxyphenyl)sulfonyl)imino)-3-oxo-5,6,7,8,11,11a-hexahydro-1H,3H-oxazolo[3,4-c][1,3]diazonin-11-yl)amino)methylene)-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  De Novo Synthesis of Modified Saxitoxins for Sodium Ion Channel Study

  摘要：

  Access to novel forms of (+)-saxitoxin (STX), a potent and selective inhibitor of voltage-gated Na+ ion channels, has been made possible through de novo synthesis. Saxitoxin is believed to lodge in the outer mouth of the channel pore, thereby stoppering ion flux. Herein, we demonstrate that modification of the C13-carbamoyl unit can be accommodated in the binding site of the protein without significantly reducing ligand-receptor affinity. These discoveries have emboldened efforts to prepare photoaffinity-labeled and other unique forms of STX as pharmacological tools for interrogating both the molecular architecture and function of Na+ channels. A synthetic plan that makes such compounds generally available is described.

  DOI：

  10.1021/ja904179f