2-(6-trifluoromethyl-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide | 546102-55-0

• 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-trifluoromethyl-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide
• 英文别名: 3-(1H-indol-3-yl)-4-[6-(trifluoromethyl)-1H-indol-3-yl]pyrrole-2,5-dione
• CAS: 546102-55-0
• 化学式: C₂₁H₁₂F₃N₃O₂
• 分子量: 395.34
• InChiKey: BWARLHDDVSJSNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(6-trifluoromethyl-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide 在 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 5.0h， 以69%的产率得到Indolocarbazole deriv. 4k
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationship, and Biological Studies of Indolocarbazoles as Potent Cyclin D1-CDK4 Inhibitors

  摘要：

  Novel substituted indolocarbazoles were synthesized, and their kinase inhibitory capability was evaluated in vitro. 6-Substituted indolocarbazoles 4 were found to be potent and selective D1/CDK4 inhibitors. 4d and 4h exhibited potent and ATP-competitive D1/CDK4 activities with IC50 values of 76 and 42 nM, respectively. Both compounds had high selectivity against the other kinases. These D1/CDK4 inhibitors inhibited tumor cell growth, arrested tumor cells at the G1 phase, and inhibited pRb phosphorylation.

  DOI：

  10.1021/jm0256169
• 作为产物：
  描述：

  吲哚-3-乙醛酸甲酯 、 6-trifluoromethyl-1H-indol-3-yl-acetamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 2-(6-trifluoromethyl-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationship, and Biological Studies of Indolocarbazoles as Potent Cyclin D1-CDK4 Inhibitors

  摘要：

  Novel substituted indolocarbazoles were synthesized, and their kinase inhibitory capability was evaluated in vitro. 6-Substituted indolocarbazoles 4 were found to be potent and selective D1/CDK4 inhibitors. 4d and 4h exhibited potent and ATP-competitive D1/CDK4 activities with IC50 values of 76 and 42 nM, respectively. Both compounds had high selectivity against the other kinases. These D1/CDK4 inhibitors inhibited tumor cell growth, arrested tumor cells at the G1 phase, and inhibited pRb phosphorylation.

  DOI：

  10.1021/jm0256169

文献信息

• US5380746A
  申请人：——

  公开号：US5380746A

  公开（公告）日：1995-01-10
• US5516915A
  申请人：——

  公开号：US5516915A

  公开（公告）日：1996-05-14
• Synthesis, Structure−Activity Relationship, and Biological Studies of Indolocarbazoles as Potent Cyclin D1-CDK4 Inhibitors
  作者：Guoxin Zhu、Scott E. Conner、Xun Zhou、Chuan Shih、Tiechao Li、Bryan D. Anderson、Harold B. Brooks、Robert Morris Campbell、Eileen Considine、Jack A. Dempsey、Margaret M. Faul、Cathy Ogg、Bharvin Patel、Richard M. Schultz、Charles D. Spencer、Beverly Teicher、Scott A. Watkins

  DOI：10.1021/jm0256169

  日期：2003.5.1

  Novel substituted indolocarbazoles were synthesized, and their kinase inhibitory capability was evaluated in vitro. 6-Substituted indolocarbazoles 4 were found to be potent and selective D1/CDK4 inhibitors. 4d and 4h exhibited potent and ATP-competitive D1/CDK4 activities with IC50 values of 76 and 42 nM, respectively. Both compounds had high selectivity against the other kinases. These D1/CDK4 inhibitors inhibited tumor cell growth, arrested tumor cells at the G1 phase, and inhibited pRb phosphorylation.