9-Bromo-3-methoxypaullone | 498557-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 9-Bromo-3-methoxypaullone
• 英文别名: 9-bromo-3-methoxy-7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one；9-bromo-3-methoxy-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-6-one
• CAS: 498557-38-3
• 化学式: C₁₇H₁₃BrN₂O₂
• 分子量: 357.206
• InChiKey: XJRRLUIRUUAFKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-Bromo-3-methoxypaullone 在 三溴化硼 、 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 14.0h， 生成 C3-Paullone
  参考文献：
  名称：

  Synthesis of Paullones with Aminoalkyl Side Chains

  摘要：

  Paullones 3 and 4 with aminoalkyl side chains in 2- or 3-position were synthesized as derivatives of kenpaullone 1. Both 3 and 4 showed the characteristic CDK1-inhibitory activity of the paullones and a modest antiproliferative activity on cultured human tumor cell lines. Hence, 3 and 4 appear to be suitable tools for affinity studies directed to find additional intracellular paullone targets.

  DOI：

  10.1002/1521-4184(200209)335:7<311::aid-ardp311>3.0.co;2-f
• 作为产物：
  描述：

  8-甲氧基-1,3,4,5-四氢-苯并[B]氮杂革-2-酮 在 magnesium(II) nitrate 、 potassium permanganate 、 sodium acetate 作用下， 以 水 、 溶剂黄146 、 叔丁醇 为溶剂， 反应 28.0h， 生成 9-Bromo-3-methoxypaullone
  参考文献：
  名称：

  Synthesis of Paullones with Aminoalkyl Side Chains

  摘要：

  Paullones 3 and 4 with aminoalkyl side chains in 2- or 3-position were synthesized as derivatives of kenpaullone 1. Both 3 and 4 showed the characteristic CDK1-inhibitory activity of the paullones and a modest antiproliferative activity on cultured human tumor cell lines. Hence, 3 and 4 appear to be suitable tools for affinity studies directed to find additional intracellular paullone targets.

  DOI：

  10.1002/1521-4184(200209)335:7<311::aid-ardp311>3.0.co;2-f

文献信息

• Evaluation and Comparison of 3D-QSAR CoMSIA Models for CDK1, CDK5, and GSK-3 Inhibition by Paullones
  作者：Conrad Kunick、Kathrin Lauenroth、Karen Wieking、Xu Xie、Christiane Schultz、Rick Gussio、Daniel Zaharevitz、Maryse Leost、Laurent Meijer、Alexander Weber、Flemming S. Jørgensen、Thomas Lemcke

  DOI：10.1021/jm0308904

  日期：2004.1.1

  With a view to the rational design of selective GSK-3beta inhibitors, 3D-QSAR CoMSIA models were developed for the inhibition of the three serine/threonine kinases CDK1/cyclin B, CDK5/p25, and GSK-3beta by compounds from the paullone inhibitor family. The models are based on the kinase inhibition data of 52 paullone entities, which were aligned by a docking routine into the ATP-binding cleft of a CDK1/cyclin B homology model. Variation of grid spacing and column filtering were used during the optimization of the models. The predictive ability of the models was shown by a leave-one-out cross-validation and the prediction of an independent set of test compounds, which were synthesized especially for this purpose. Besides paullones with the basic indolo [3,2-d] [1]benzazepine core, the test set comprised novel thieno [3',2':2,3]-azepino[4,5-b]indoles, pyrido[2',3':2,3]azepino[4,5-b]indoles, and a pyrido[3',2':4,5]pyrrolo[3,2-d] [1]benzazepine. The best statistical values for the CoMSIA were obtained for the CDK1-models (r(2) = 0.929 and q(2) = 0.699), which were clearly superior to the models for CDK5 (r(2) = 0.874 and q(2) = 0.652) and GSK-3 (r(2) = 0.871 and q(2) = 0.554).
• Synthesis of Paullones with Aminoalkyl Side Chains
  作者：Karen Wieking、Marie Knockaert、Maryse Leost、Daniel W. Zaharevitz、Laurent Meijer、Conrad Kunick

  DOI：10.1002/1521-4184(200209)335:7<311::aid-ardp311>3.0.co;2-f

  日期：2002.9

  Paullones 3 and 4 with aminoalkyl side chains in 2- or 3-position were synthesized as derivatives of kenpaullone 1. Both 3 and 4 showed the characteristic CDK1-inhibitory activity of the paullones and a modest antiproliferative activity on cultured human tumor cell lines. Hence, 3 and 4 appear to be suitable tools for affinity studies directed to find additional intracellular paullone targets.