(S)-methyl 2-<<4-(4-methoxytetrahydropyranoyl)>oxy>3-<<<<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl><2-(3-indolyl)ethyl>amino>oxy>methyl>thio>propanoate | 142564-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (S)-methyl 2-<<4-(4-methoxytetrahydropyranoyl)>oxy>3-<<<<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl><2-(3-indolyl)ethyl>amino>oxy>methyl>thio>propanoate
• 英文别名: methyl (2S)-3-[[2-(1H-indol-3-yl)ethyl-(2-trimethylsilylethoxycarbonyl)amino]oxymethylsulfanyl]-2-(4-methoxyoxan-4-yl)oxypropanoate
• CAS: 142564-28-1
• 化学式: C₂₇H₄₂N₂O₈SSi
• 分子量: 582.791
• InChiKey: ZJOINSOZFZUOIW-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  39.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  108.55
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-<<4-(4-methoxytetrahydropyranoyl)>oxy>3-<<<<<<<2-(trimethylsilyl)ethyl>oxy>carbonyl><2-(3-indolyl)ethyl>amino>oxy>methyl>thio>propanoate 在 potassium fluoride 、 四丁基氯化铵 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.0h， 生成 (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 2-O-<4-(4-methoxytetrahydropyranyl)>-3-(acetylthio)propanoate 在 氢氧化钾 、 苄基三乙基氯化铵 、 sodium methylate 、 sodium hydride 、 sodium iodide 作用下， 以 甲醇 为溶剂， 反应 1.75h， 生成 (S)-methyl 2-<<4-(4-methoxytetrahydropyranoyl)>oxy>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

文献信息

• Intramolecular Pictet-Spengler reaction of Nb-Alkoxytryptamines. 4. A study towards diastereocontrol in the synthesis of tetracyclic eudistomins
  作者：Jan H. van Maarseveen、Hans W. Scheeren、Chris G. Kruse

  DOI：10.1016/s0040-4020(01)80376-8

  日期：1993.3

  methylated derivative was also synthesized giving the interesting cis/trans pentacyclic spiro compounds 19 and 20. These results are interpreted in terms of a kinetically favoured electrophilic attack at the indole-3 position, whereas β-carboline formation is the result of a slower route via electrophilic attack at the indole-2 position.

  描述了在合成四环大黄连素中分子内Pictet-Spengler缩合的非对映选择性。N b-烷氧基色胺15a–m与不同大小的基团R 2合成。7成员草硫氮杂ze环的闭合以66–98％的产率完成。使用分子内方法，可以实现非天然反式异构体的非对映选择性。还合成了吲哚甲基化衍生物，得到了有趣的顺式/反式五环螺化合物19和20。这些结果被解释为在吲哚3位置的动力学上有利于亲电子的攻击，而β-咔啉的形成是在吲哚2位置上通过亲电子攻击的较慢途径的结果。