(2E/Z)-5-(9-bromobenzo[h]isoquinolin-6-yl)acrylonitrile | 919293-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (2E/Z)-5-(9-bromobenzo[h]isoquinolin-6-yl)acrylonitrile
• 英文别名: 3-(9-bromobenzo[h]isoquinolin-6-yl)acrylonitrile；3-(9-Bromobenzo[h]isoquinolin-6-yl)prop-2-enenitrile；3-(9-bromobenzo[h]isoquinolin-6-yl)prop-2-enenitrile
• CAS: 919293-24-6
• 化学式: C₁₆H₉BrN₂
• 分子量: 309.165
• InChiKey: MVRDTLVVRPXEEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E/Z)-5-(9-bromobenzo[h]isoquinolin-6-yl)acrylonitrile 在 sodium tetrahydroborate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 1.0h， 生成 5-(9-bromobenzo[h]isoquinolin-6-yl)propanenitrile
  参考文献：
  名称：

  Synthesis and evaluation of substituted benzoisoquinolinones as potent inhibitors of Chk1 kinase

  摘要：

  From HTS lead 1, a novel benzoisoquinolinone class of ATP-competitive Chk1 inhibitors was devised and synthesized via a photochemical route. Using X-ray crystallography as a guide, potency was rapidly enhanced through the installation of a tethered basic amine designed to interact with an acidic residue (Glu91) in the enzyme pocket. Further SAR was explored at the solvent front and near to the H1 pocket and resulted in the discovery of low MW, sub-nanomolar inhibitors of Chk1.

  DOI：

  10.1016/j.bmcl.2007.09.007
• 作为产物：
  描述：

  9-溴苯并[h]异喹啉-6-甲醛 、 氰甲基磷酸二乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 (2E/Z)-5-(9-bromobenzo[h]isoquinolin-6-yl)acrylonitrile
  参考文献：
  名称：

  WO2007/8502

  摘要：

  公开号：

文献信息

• Synthesis and evaluation of substituted benzoisoquinolinones as potent inhibitors of Chk1 kinase
  作者：Robert M. Garbaccio、Shaei Huang、Edward S. Tasber、Mark E. Fraley、Youwei Yan、Sanjeev Munshi、Mari Ikuta、Lawrence Kuo、Constanine Kreatsoulas、Steve Stirdivant、Bob Drakas、Keith Rickert、Eileen S. Walsh、Kelly A. Hamilton、Carolyn A. Buser、James Hardwick、Xianzhi Mao、Stephen C. Beck、Marc T. Abrams、Weikang Tao、Rob Lobell、Laura Sepp-Lorenzino、George D. Hartman

  DOI：10.1016/j.bmcl.2007.09.007

  日期：2007.11

  From HTS lead 1, a novel benzoisoquinolinone class of ATP-competitive Chk1 inhibitors was devised and synthesized via a photochemical route. Using X-ray crystallography as a guide, potency was rapidly enhanced through the installation of a tethered basic amine designed to interact with an acidic residue (Glu91) in the enzyme pocket. Further SAR was explored at the solvent front and near to the H1 pocket and resulted in the discovery of low MW, sub-nanomolar inhibitors of Chk1.
• WO2007/8502
  申请人：——

  公开号：——

  公开（公告）日：——