3-(indol-3-ylmethylene)succinic anhydride | 149949-66-6

• 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: 3-(indol-3-ylmethylene)succinic anhydride
• 英文别名: 3-(1H-indol-3-yl-methyl)succinic anhydride；3-[(1H-indol-3-yl)methyl]oxolane-2,5-dione；3-(1H-indol-3-ylmethyl)oxolane-2,5-dione
• CAS: 149949-66-6
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: SZVKDHWCTUYZAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(indol-3-ylmethylene)succinic anhydride 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 1-oxo-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
  参考文献：
  名称：

  A SHORT SYNTHESIS OF THE CARBAZOLE ALKALOID CLAUSINE E

  摘要：

  DOI：

  10.1080/00304940609356448
• 作为产物：
  描述：

  3-carboxy-4-(indol-3-yl)butanoic acid 在 乙酸酐 作用下， 反应 6.0h， 生成 3-(indol-3-ylmethylene)succinic anhydride
  参考文献：
  名称：

  Tryptophan-Derived NK1 Antagonists: Conformationally Constrained Heterocyclic Bioisosteres of the Ester Linkage

  摘要：

  The 3,5-bis(trifluoromethyl)benzyl ester of N-acetyl-L-tryptophan 1 (L-732,138) has been identified previously as a potent and selective substance P receptor antagonist. A series of analogs which introduced a 6-membered heterocyclic ring into the backbone of this structure were prepared for evaluation as bioisosteric replacements of the ester linkage of 1. The 2,5-dioxopiperazine 2 had very weak receptor affinity, but 2-oxopiperazine 5 exhibited modest activity. Examination of the conformations accessible to the substituents on these templates led to exploration of the corresponding 5-membered heterocyclic rings. This study culminated in the identification of oxazolidinedione 14 as a suitable ester mimic in terms of the retention of good NK1 binding affinity.

  DOI：

  10.1021/jm00006a011

文献信息

• Tryptophan-Derived NK1 Antagonists: Conformationally Constrained Heterocyclic Bioisosteres of the Ester Linkage
  作者：Richard T. Lewis、Angus M. Macleod、Kevin J. Merchant、Fintan Kelleher、Ian Sanderson、Richard H. Herbert、Margaret A. Cascieri、Sharon Sadowski、Richard G. Ball、Karst Hoogsteen

  DOI：10.1021/jm00006a011

  日期：1995.3

  The 3,5-bis(trifluoromethyl)benzyl ester of N-acetyl-L-tryptophan 1 (L-732,138) has been identified previously as a potent and selective substance P receptor antagonist. A series of analogs which introduced a 6-membered heterocyclic ring into the backbone of this structure were prepared for evaluation as bioisosteric replacements of the ester linkage of 1. The 2,5-dioxopiperazine 2 had very weak receptor affinity, but 2-oxopiperazine 5 exhibited modest activity. Examination of the conformations accessible to the substituents on these templates led to exploration of the corresponding 5-membered heterocyclic rings. This study culminated in the identification of oxazolidinedione 14 as a suitable ester mimic in terms of the retention of good NK1 binding affinity.
• A SHORT SYNTHESIS OF THE CARBAZOLE ALKALOID CLAUSINE E
  作者：Jan Bergman、Ann-Louise Johnson

  DOI：10.1080/00304940609356448

  日期：2006.12