6,6-dimethyl-2-(4-nitrophenyl)-1-(3-bromophenyl)-1,5,6,7-tetrahydroindol-4-one | 675106-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 6,6-dimethyl-2-(4-nitrophenyl)-1-(3-bromophenyl)-1,5,6,7-tetrahydroindol-4-one
• 英文别名: 1-(3-Bromophenyl)-6,6-dimethyl-2-(4-nitrophenyl)-5,7-dihydroindol-4-one
• CAS: 675106-41-9
• 化学式: C₂₂H₁₉BrN₂O₃
• 分子量: 439.308
• InChiKey: YXVVXJHEUGFLQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,6-dimethyl-2-(4-nitrophenyl)-1-(3-bromophenyl)-1,5,6,7-tetrahydroindol-4-one 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以88%的产率得到4H-Indol-4-one,1-(3-bromophenyl)-1,5,6,7-tetrahydro-6,6-dimethyl-2-(4-nitrophenyl)-,oxime
  参考文献：
  名称：

  Tetrahydropyrrolo[3,2-c]azepin-4-ones as a new class of cytotoxic compounds

  摘要：

  Pyrroloazepinones 8a-j and 9a-j were designed by structural modification of lead compound 3. These compounds were tested on five tumor cell lines to determine the role of the azeto ring and the 2-methyl substituent in the cytotoxicity of compound 3. Our results show that compounds 8a-j (R-1 = CH3) have dramatically reduced cytotoxicity, resulting from the loss of the azeto moiety of lead compound 3. By contrast, azepinones 9a-j (R-1 = 4-nitrophenyl) inhibited the proliferation of almost all cancer cell lines tested even though they lack the azeto ring. Preliminary SAR studies with these compounds revealed the importance of halogens at the para- or meta-position of the 1-phenyl moiety. Additionally, derivatives 9a (R-2 = H), 9e (R-2 = 4-F), and 9g (R-2 = 4-OMe) were selectively cytotoxic to U-251 cells. However, none of the pyrroloazepinones inhibited the enzymatic activity of CDK1/cyclin B, CDK5/p25, and GSK-3. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.012
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 zirconium sulphate 、 potassium carbonate 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 51.0h， 生成 6,6-dimethyl-2-(4-nitrophenyl)-1-(3-bromophenyl)-1,5,6,7-tetrahydroindol-4-one
  参考文献：
  名称：

  Tetrahydropyrrolo[3,2-c]azepin-4-ones as a new class of cytotoxic compounds

  摘要：

  Pyrroloazepinones 8a-j and 9a-j were designed by structural modification of lead compound 3. These compounds were tested on five tumor cell lines to determine the role of the azeto ring and the 2-methyl substituent in the cytotoxicity of compound 3. Our results show that compounds 8a-j (R-1 = CH3) have dramatically reduced cytotoxicity, resulting from the loss of the azeto moiety of lead compound 3. By contrast, azepinones 9a-j (R-1 = 4-nitrophenyl) inhibited the proliferation of almost all cancer cell lines tested even though they lack the azeto ring. Preliminary SAR studies with these compounds revealed the importance of halogens at the para- or meta-position of the 1-phenyl moiety. Additionally, derivatives 9a (R-2 = H), 9e (R-2 = 4-F), and 9g (R-2 = 4-OMe) were selectively cytotoxic to U-251 cells. However, none of the pyrroloazepinones inhibited the enzymatic activity of CDK1/cyclin B, CDK5/p25, and GSK-3. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.012

文献信息

• An Efficient Synthesis of 6,6-Dimethyl-2-(4-nitrophenyl)-1-(R-phenyl)-4,5,6,7-tetrahydro-1H-4-indolones Using a Solid Sulfated Zirconia as Catalyst
  作者：Roberto Martínez、Leticia Lomas、Guillermo Negrón、Deyanira Ángeles、Ángeles Martínez、Manuel Ramírez

  DOI：10.3987/com-03-9923

  日期：——
• Tetrahydropyrrolo[3,2-c]azepin-4-ones as a new class of cytotoxic compounds
  作者：Roberto Martínez、J. Gustavo Ávila、Ma. Teresa Ramírez、Araceli Pérez、Ángeles Martínez

  DOI：10.1016/j.bmc.2006.02.012

  日期：2006.6

  Pyrroloazepinones 8a-j and 9a-j were designed by structural modification of lead compound 3. These compounds were tested on five tumor cell lines to determine the role of the azeto ring and the 2-methyl substituent in the cytotoxicity of compound 3. Our results show that compounds 8a-j (R-1 = CH3) have dramatically reduced cytotoxicity, resulting from the loss of the azeto moiety of lead compound 3. By contrast, azepinones 9a-j (R-1 = 4-nitrophenyl) inhibited the proliferation of almost all cancer cell lines tested even though they lack the azeto ring. Preliminary SAR studies with these compounds revealed the importance of halogens at the para- or meta-position of the 1-phenyl moiety. Additionally, derivatives 9a (R-2 = H), 9e (R-2 = 4-F), and 9g (R-2 = 4-OMe) were selectively cytotoxic to U-251 cells. However, none of the pyrroloazepinones inhibited the enzymatic activity of CDK1/cyclin B, CDK5/p25, and GSK-3. (c) 2006 Elsevier Ltd. All rights reserved.