NCS-741772 | 1043868-47-8

• 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: NCS-741772
• 英文别名: (3E)-5-bromo-3-[[6-[(E)-(5-bromo-2-oxo-1H-indol-3-ylidene)methyl]pyridin-2-yl]methylidene]-1H-indol-2-one
• CAS: 1043868-47-8
• 化学式: C₂₃H₁₃Br₂N₃O₂
• 分子量: 523.183
• InChiKey: VYJXFQGITUDKQS-XOBNHNQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡啶-2,6-二甲醛 、 5-溴氧化吲哚 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 NCS-741772
  参考文献：
  名称：

  Antitumor Activity of Bis-indole Derivatives

  摘要：

  This paper reports the synthesis of compounds formed by two indole systems separated by a heterocycle (pyridine or piperazine). As a primary screening, the new compounds were submitted to the National Cancer Institute for evaluation of antitumor activity in the human cell line screen. The pyridine derivatives were far more active than the piperazine derivatives. For the study of the mechanism of action, the most active compounds were subjected to COMPARE analysis and to further biological tests including proteasome inhibition and inhibition of plasma membrane electron transport. The compound bearing the 5-methoxy2-indolinone moiety was subjected to the first in vivo experiment (hollow fiber assay) and was active. It was therefore selected for the second in vivo experiment (human tumor xenograft in mice). In conclusion we demonstrated that this approach was successful, since some of the compounds described are much more active than the numerous, so far prepared and tested 3-indolylmethylene-2-indolinones.

  DOI：

  10.1021/jm800194k

文献信息

• Antitumor Activity of Bis-indole Derivatives
  作者：Aldo Andreani、Silvia Burnelli、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Laura Landi、Cecilia Prata、Michael V. Berridge、Carole Grasso、Heinz-Herbert Fiebig、Gerhard Kelter、Angelika M. Burger、Mark W. Kunkel

  DOI：10.1021/jm800194k

  日期：2008.8.1

  This paper reports the synthesis of compounds formed by two indole systems separated by a heterocycle (pyridine or piperazine). As a primary screening, the new compounds were submitted to the National Cancer Institute for evaluation of antitumor activity in the human cell line screen. The pyridine derivatives were far more active than the piperazine derivatives. For the study of the mechanism of action, the most active compounds were subjected to COMPARE analysis and to further biological tests including proteasome inhibition and inhibition of plasma membrane electron transport. The compound bearing the 5-methoxy2-indolinone moiety was subjected to the first in vivo experiment (hollow fiber assay) and was active. It was therefore selected for the second in vivo experiment (human tumor xenograft in mice). In conclusion we demonstrated that this approach was successful, since some of the compounds described are much more active than the numerous, so far prepared and tested 3-indolylmethylene-2-indolinones.