(S)-methyl 2-hydroxy-3-<<<<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl><2-(3-indolyl)ethyl>amino>oxy>methyl>thio>propanoate | 142564-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-methyl 2-hydroxy-3-<<<<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl><2-(3-indolyl)ethyl>amino>oxy>methyl>thio>propanoate
• 英文别名: methyl (2S)-2-hydroxy-3-[[2-(1H-indol-3-yl)ethyl-(2-trimethylsilylethoxycarbonyl)amino]oxymethylsulfanyl]propanoate
• CAS: 142564-29-2
• 化学式: C₂₁H₃₂N₂O₆SSi
• 分子量: 468.646
• InChiKey: VOQGBCHEVAPFOX-LJQANCHMSA-N

物化性质

• 沸点：
  617.7±55.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  101.09
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-hydroxy-3-<<<<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl><2-(3-indolyl)ethyl>amino>oxy>methyl>thio>propanoate 在 potassium fluoride 、 四丁基氯化铵 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以79%的产率得到(S)-methyl 2-hydroxy-3-<<<<<2-(3-indolyl)ethyl>amino>oxy>methyl>thio>propanoate
  参考文献：
  名称：

  Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines

  摘要：

  The in vitro antiviral and antitumor activities of (-)-debromoeudistomin K (1a) and 10 structural analogues (1b-1j and 11) were evaluated. The synthesis was accomplished with an intramolecular Pictet-Spengler condensation reaction as the key step. This examination revealed some structural and stereochemical features that are important for both the antiviral and antitumor activities. The most striking points for activity are the necessity to have the correct natural stereochemistry at both C(1) and C(13b) and the presence of the C(1)-NH2 substituent. As was revealed before with naturally isolated eudistomins a substituent in the indole ring greatly influences the biological activity. The 5-OMe derivative Ih shows high potency in both antiviral and antitumor models.

  DOI：

  10.1021/jm00095a019
• 作为产物：
  描述：

  (S)-methyl 3-(chloromethylthio)-2-<<4-(4-methoxytetrahydropyranyl)>oxy>propanoate 在 sodium hydride 、 对甲苯磺酸 、 sodium iodide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (S)-methyl 2-hydroxy-3-<<<<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl><2-(3-indolyl)ethyl>amino>oxy>methyl>thio>propanoate
  参考文献：
  名称：

  Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines

  摘要：

  The in vitro antiviral and antitumor activities of (-)-debromoeudistomin K (1a) and 10 structural analogues (1b-1j and 11) were evaluated. The synthesis was accomplished with an intramolecular Pictet-Spengler condensation reaction as the key step. This examination revealed some structural and stereochemical features that are important for both the antiviral and antitumor activities. The most striking points for activity are the necessity to have the correct natural stereochemistry at both C(1) and C(13b) and the presence of the C(1)-NH2 substituent. As was revealed before with naturally isolated eudistomins a substituent in the indole ring greatly influences the biological activity. The 5-OMe derivative Ih shows high potency in both antiviral and antitumor models.

  DOI：

  10.1021/jm00095a019