2-[[6-methoxy-2-(4-methoxyphenyl)-1H-indol-3-yl]methylidene]propanedinitrile | 920514-60-9

• 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
• 英文名称: 2-[[6-methoxy-2-(4-methoxyphenyl)-1H-indol-3-yl]methylidene]propanedinitrile
• CAS: 920514-60-9
• 化学式: C₂₀H₁₅N₃O₂
• 分子量: 329.358
• InChiKey: FZQNHLVXTYFKKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  81.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-甲氧基-2-(4-甲氧基苯基)-1H-吲哚-3-甲醛 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以96%的产率得到2-[[6-methoxy-2-(4-methoxyphenyl)-1H-indol-3-yl]methylidene]propanedinitrile
  参考文献：
  名称：

  [(2-Phenylindol-3-yl)methylene]propanedinitriles inhibit the growth of breast cancer cells by cell cycle arrest in G2/M phase and apoptosis

  摘要：

  Cell cycle arrest of malignant cells is an important option for cancer treatment. In this study, we modified the structure of antimitotic 2-phenylindole-3-carbaldehydes by condensation with malononitrile. The resulting methylene propanedinitriles inhibited the growth of MDA-MB 231 and MCF-7 breast cancer cells with IC50 values below 100 nM. Though they exhibited similar structure-activity relationships as the aldehydes, they did not inhibit tubulin polymerization but were capable of blocking the cell cycle in G(2)/M phase. The cell cycle arrest was accompanied by apoptosis as demonstrated by the activation of caspases 3 and 9. Since the new 2-phenylindole derivatives also inhibited the growth of transplanted MXT mouse mammary tumors, they are interesting candidates for further development. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.046

文献信息

• 3-Indolylmethylen-Derivate mit cytostatischer Wirkung
  申请人：Universitaet Regensburg

  公开号：EP1746087A1

  公开（公告）日：2007-01-24

  Die Erfindung betrifft 3-Indolylmethylen-Derivate mit der allgemeinen Formel II mit cytostatischer Wirkung, sowie ein Verfahren zur Herstellung der 3-Indolylmethylen-Derivate, deren Verwendung zur Herstellung von Arzneimitteln sowie 3-Indolylmethylen-Derivate enthaltende pharmazeutische Zusammensetzungen.

  本发明涉及具有通式 II 并具有细胞抑制活性的 3-吲哚亚甲基衍生物，以及制备 3-吲哚亚甲基衍生物的工艺、其在制备含有 3-吲哚亚甲基衍生物的药物和药物组合物中的用途。
• [(2-Phenylindol-3-yl)methylene]propanedinitriles inhibit the growth of breast cancer cells by cell cycle arrest in G2/M phase and apoptosis
  作者：Michaela Pojarová、Doris Kaufmann、Robert Gastpar、Tsuyuki Nishino、Przemyslaw Reszka、Patrick J. Bednarski、Erwin von Angerer

  DOI：10.1016/j.bmc.2007.07.046

  日期：2007.12

  Cell cycle arrest of malignant cells is an important option for cancer treatment. In this study, we modified the structure of antimitotic 2-phenylindole-3-carbaldehydes by condensation with malononitrile. The resulting methylene propanedinitriles inhibited the growth of MDA-MB 231 and MCF-7 breast cancer cells with IC50 values below 100 nM. Though they exhibited similar structure-activity relationships as the aldehydes, they did not inhibit tubulin polymerization but were capable of blocking the cell cycle in G(2)/M phase. The cell cycle arrest was accompanied by apoptosis as demonstrated by the activation of caspases 3 and 9. Since the new 2-phenylindole derivatives also inhibited the growth of transplanted MXT mouse mammary tumors, they are interesting candidates for further development. (C) 2007 Elsevier Ltd. All rights reserved.