3-Azaphenanthren-6-carbonitril | 82649-92-1

• 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: 3-Azaphenanthren-6-carbonitril
• 英文别名: Benz[h]isoquinoline-6-carbonitrile；benzo[h]isoquinoline-6-carbonitrile
• CAS: 82649-92-1
• 化学式: C₁₄H₈N₂
• 分子量: 204.231
• InChiKey: UNHQLJAGYYZXPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  0
• 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：

  3-Azaphenanthren-6-carbonitril 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 Benzo[h]isoquinoline-6-carboxylic acid
  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：

  (E)-2-phenyl-3-pyridin-4-ylprop-2-enenitrile 在 氧气 作用下， 以 叔丁醇 、 苯 为溶剂， 以30%的产率得到3-Azaphenanthren-6-carbonitril
  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

文献信息

• Inhibitors of Checkpoint Kinases
  申请人：Arrington Kenneth L.

  公开号：US20090258852A1

  公开（公告）日：2009-10-15

  The instant invention provides for compounds which comprise benzoisoquinolinones and aza derivatives that inhibit CHK1 activity. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting CHK1 activity by administering the compound to a patient in need of treatment of cancer.

  本发明提供了一种由苯并异喹啉酮和氮杂衍生物组成的化合物，其抑制CHK1活性。本发明还提供了包含这种抑制剂化合物的组合物以及通过将该化合物用于需要治疗癌症的患者来抑制CHK1活性的方法。
• Horner, Michael; Huenig, Siegfried, Liebigs Annalen der Chemie, 1982, # 6, p. 1183 - 1210
  作者：Horner, Michael、Huenig, Siegfried

  DOI：——

  日期：——
• HORNER, M.;HUENIG, S., LIEBIGS ANN. CHEM., 1982, N 6, 1183-1210
  作者：HORNER, M.、HUENIG, S.

  DOI：——

  日期：——
• 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.