cis-dihydroarcyriarubin C | 948849-04-5

• 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: cis-dihydroarcyriarubin C
• 英文别名: cis-3,4-bis-(6-hydroxy-1H-indol-3-yl)-2,5-pyrrolidinedione；(3S,4R)-3,4-bis(6-hydroxy-1H-indol-3-yl)pyrrolidine-2,5-dione
• CAS: 948849-04-5
• 化学式: C₂₀H₁₅N₃O₄
• 分子量: 361.357
• InChiKey: MDOQJLLAKJRIGD-HDICACEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-dihydroarcyriarubin C 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到trans-dihydroarcyriarubin C
  参考文献：
  名称：

  Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloids from the myxomycete Arcyria ferruginea: An approach for Wnt signal inhibitor

  摘要：

  To determine the stereochemistry of dihydroarcyriarubin C (1), new bisindole alkaloid isolated from the myxomycete Arcyriajerruginea, cis- (2) and trans-dihydroarcyriarubin C (3) were synthesized. Comparison of their NMR characteristics allowed the trans stereochemistry of the natural product to be confirmed. Moreover, the Writ signal inhibitory activities of 2 and 3 were compared with that of arcyriaflavin C (4), which is a natural product containing a bond between C-2 and C-T. The cis-dihydroar-cyriarubin C (2) showed moderate inhibition of Wnt signal transcription, which suggests that bisindole frameworks might be useful as small-molecule Writ signal inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.033
• 作为产物：
  描述：

  2,3-bis-(6-benzyloxy-1H-indol-3-yl)-maleimide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以95%的产率得到cis-dihydroarcyriarubin C
  参考文献：
  名称：

  Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloids from the myxomycete Arcyria ferruginea: An approach for Wnt signal inhibitor

  摘要：

  To determine the stereochemistry of dihydroarcyriarubin C (1), new bisindole alkaloid isolated from the myxomycete Arcyriajerruginea, cis- (2) and trans-dihydroarcyriarubin C (3) were synthesized. Comparison of their NMR characteristics allowed the trans stereochemistry of the natural product to be confirmed. Moreover, the Writ signal inhibitory activities of 2 and 3 were compared with that of arcyriaflavin C (4), which is a natural product containing a bond between C-2 and C-T. The cis-dihydroar-cyriarubin C (2) showed moderate inhibition of Wnt signal transcription, which suggests that bisindole frameworks might be useful as small-molecule Writ signal inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.033

文献信息

• Synthesis, determination of stereochemistry, and evaluation of new bisindole alkaloids from the myxomycete Arcyria ferruginea: An approach for Wnt signal inhibitor
  作者：Kouken Kaniwa、Midori A. Arai、Xiaofan Li、Masami Ishibashi

  DOI：10.1016/j.bmcl.2007.05.033

  日期：2007.8

  To determine the stereochemistry of dihydroarcyriarubin C (1), new bisindole alkaloid isolated from the myxomycete Arcyriajerruginea, cis- (2) and trans-dihydroarcyriarubin C (3) were synthesized. Comparison of their NMR characteristics allowed the trans stereochemistry of the natural product to be confirmed. Moreover, the Writ signal inhibitory activities of 2 and 3 were compared with that of arcyriaflavin C (4), which is a natural product containing a bond between C-2 and C-T. The cis-dihydroar-cyriarubin C (2) showed moderate inhibition of Wnt signal transcription, which suggests that bisindole frameworks might be useful as small-molecule Writ signal inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.