(S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester | 274677-49-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester
• 英文别名: methyl (2S)-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]-3-(1H-indol-3-yl)propanoate
• CAS: 274677-49-5
• 化学式: C₂₁H₂₂N₂O₅
• 分子量: 382.416
• InChiKey: KUDVLLUGTLTMBC-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester 在 哌啶 、 sodium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.67h， 生成 (1S,12S,15S)-12-(4-hydroxy-3,5-dimethoxyphenyl)-10,13,19-triazapentacyclo[11.7.0.03,11.04,9.015,19]icosa-3(11),4,6,8-tetraene-14,20-dione
  参考文献：
  名称：

  Synthesis and Evaluation of Tryprostatin B and Demethoxyfumitremorgin C Analogues

  摘要：

  Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-TrP-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.

  DOI：

  10.1021/jm9905662
• 作为产物：
  描述：

  丁香醛 、 L-色氨酸甲酯 在 原甲酸三甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 (S)-2-{[1-(4-Hydroxy-3,5-dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Tryprostatin B and Demethoxyfumitremorgin C Analogues

  摘要：

  Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-TrP-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.

  DOI：

  10.1021/jm9905662