6-bromo-4-{4-[(4-methylpiperazin-1-yl)-phenylamino]methylene}-4H-isoquinoline-1,3-dione | 943751-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-bromo-4-{4-[(4-methylpiperazin-1-yl)-phenylamino]methylene}-4H-isoquinoline-1,3-dione
• 英文别名: 6-bromo-4-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]isoquinoline-1,3-dione
• CAS: 943751-13-1
• 化学式: C₂₁H₂₁BrN₄O₂
• 分子量: 441.327
• InChiKey: XSWYPCMJALBXBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.68
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  苯磺酰胺 、 6-bromo-4-{4-[(4-methylpiperazin-1-yl)-phenylamino]methylene}-4H-isoquinoline-1,3-dione 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 allylchloro[1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidine]palladium(II) 、 potassium tert-butylate 作用下， 反应 0.25h， 生成 N-[4-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]-1,3-dioxoisoquinolin-6-yl]benzenesulfonamide
  参考文献：
  名称：

  Lead identification to generate isoquinolinedione inhibitors of insulin-like growth factor receptor (IGF-1R) for potential use in cancer treatment

  摘要：

  Insulin-like growth factor receptor (IGF-1R) is a growth factor receptor tyrosine kinase that acts as a critical mediator of cell proliferation and survival. This receptor is over-expressed or activated in tumor cells and is emerging as a novel target in cancer therapy. Efforts in our "Hit to Lead'' group have generated a novel series of submicromolar IGF-1R inhibitors based on a isoquinolinedione template originating from a Lance enzyme HTS screen. Chemical triage and parallel synthesis incorporating focused library arrays were instrumental in moving these investigations through the Wyeth exploratory medicinal chemistry process. The strategies, synthesis, and SAR behind this interesting kinase scaffold will be described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.044
• 作为产物：
  描述：

  6-bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione 、 4-(4-甲基哌嗪)苯胺 在 乙醚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以to yield 1.23 g of 6-bromo-4-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-4H-isoquinoline-1,3-dione的产率得到6-bromo-4-{4-[(4-methylpiperazin-1-yl)-phenylamino]methylene}-4H-isoquinoline-1,3-dione
  参考文献：
  名称：

  Substituted isoquinoline-1,3(2H,4H)-diones, 1-thioxo,1,4-dihydro-2H-isoquinoline-3-ones and 1,4-dihyro-3 (2H)-isoquinolones and methods of use thereof

  摘要：

  这项发明提供了式（I）的化合物，其结构为G1，G2，G3，G4，A1，A2，Y1，Y2，L1，Z，e和f在此定义，或其药学上可接受的盐，用于治疗或预防癌症。

  公开号：

  US07713994B2

文献信息

• Substituted isoquinoline-1,3(2H,4H)-diones, 1-thioxo-1,4-dihydro-2H-isoquinoline-3-ones and 1,4-dihydro-3 (2H)-isoquinolones and methods of use thereof
  申请人：Tsou Hwei-Ru

  公开号：US20080085890A1

  公开（公告）日：2008-04-10

  This invention provides compounds of Formula (I), having the structure where G 1 , G 2 , G 3 , G 4 , A 1 , A 2 , Y 1 , Y 2 , L 1 , Z, e and f are defined herein, or a pharmaceutically acceptable salt thereof, which are useful for treating or preventing cancer.

  这项发明提供了公式（I）的化合物，其结构为其中G1、G2、G3、G4、A1、A2、Y1、Y2、L1、Z、e和f在此定义，或其药学上可接受的盐，可用于治疗或预防癌症。