1-[3-[1-(1-乙酰基吲哚-3-基)乙烯基]吲哚-1-基]乙酮 | 69262-87-9

• 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
• 中文名称: 1-[3-[1-(1-乙酰基吲哚-3-基)乙烯基]吲哚-1-基]乙酮
• 英文名称: 1,1-bis-(1-acetyl-indol-3-yl)-ethene
• 英文别名: 1,1-Bis-(1-acetyl-indol-3-yl)-aethen；1-(3-(1-(1-Acetyl-1H-indol-3-yl)vinyl)-1H-indol-1-yl)-1-ethanone；1-[3-[1-(1-acetylindol-3-yl)ethenyl]indol-1-yl]ethanone
• CAS: 69262-87-9
• 化学式: C₂₂H₁₈N₂O₂
• 分子量: 342.397
• InChiKey: NUWOKANBIFXVGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  44
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[3-[1-(1-乙酰基吲哚-3-基)乙烯基]吲哚-1-基]乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以80%的产率得到3-[1-(1H-indol-3-yl)ethenyl]-1H-indole
  参考文献：
  名称：

  Computer-Aided Rational Drug Design:  A Novel Agent (SR13668) Designed to Mimic the Unique Anticancer Mechanisms of Dietary Indole-3-Carbinol to Block Akt Signaling

  摘要：

  Indole-3-carbinol (I3C) is a naturally occurring anticancer agent and has entered clinical trials for cancer prevention. However, the clinical development of I3C has been impeded by its poor metabolic profile. The active components of I3C were used to develop a novel class of indole analogs to optimize I3C's anticancer actions, including blocking growth factor-stimulated Akt activation. The most promising of these analogs, SR13668, exhibited potent oral anticancer activity against various cancers and no significant toxicity.

  DOI：

  10.1021/jm070040e
• 作为产物：
  描述：

  2-甲基-2-恶唑啉 、 吲哚 、 乙酸酐 以65%的产率得到1-[3-[1-(1-乙酰基吲哚-3-基)乙烯基]吲哚-1-基]乙酮
  参考文献：
  名称：

  Computer-Aided Rational Drug Design:  A Novel Agent (SR13668) Designed to Mimic the Unique Anticancer Mechanisms of Dietary Indole-3-Carbinol to Block Akt Signaling

  摘要：

  Indole-3-carbinol (I3C) is a naturally occurring anticancer agent and has entered clinical trials for cancer prevention. However, the clinical development of I3C has been impeded by its poor metabolic profile. The active components of I3C were used to develop a novel class of indole analogs to optimize I3C's anticancer actions, including blocking growth factor-stimulated Akt activation. The most promising of these analogs, SR13668, exhibited potent oral anticancer activity against various cancers and no significant toxicity.

  DOI：

  10.1021/jm070040e

文献信息

• 685. The reaction between indole and acetic anhydride
  作者：J. E. Saxton

  DOI：10.1039/jr9520003592

  日期：——
• BERGMAN, J.;SJOEBERG, B., HETEROCYCLES, 1982, 19, N 2, 301-304
  作者：BERGMAN, J.、SJOEBERG, B.

  DOI：——

  日期：——
• Computer-Aided Rational Drug Design:  A Novel Agent (SR13668) Designed to Mimic the Unique Anticancer Mechanisms of Dietary Indole-3-Carbinol to Block Akt Signaling
  作者：Wan-Ru Chao、Dawn Yean、Khalid Amin、Carol Green、Ling Jong

  DOI：10.1021/jm070040e

  日期：2007.7.1

  Indole-3-carbinol (I3C) is a naturally occurring anticancer agent and has entered clinical trials for cancer prevention. However, the clinical development of I3C has been impeded by its poor metabolic profile. The active components of I3C were used to develop a novel class of indole analogs to optimize I3C's anticancer actions, including blocking growth factor-stimulated Akt activation. The most promising of these analogs, SR13668, exhibited potent oral anticancer activity against various cancers and no significant toxicity.