7-(5-氨基-2-氯-苯基)-5-甲基-苯并[1,2,4]三嗪-3-基胺 | 1007224-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 7-(5-氨基-2-氯-苯基)-5-甲基-苯并[1,2,4]三嗪-3-基胺
• 英文名称: 7-(5-Amino-2-chlorophenyl)-5-methyl-1,2,4-benzotriazin-3-amine
• CAS: 1007224-62-5
• 化学式: C₁₄H₁₂ClN₅
• 分子量: 285.736
• InChiKey: WNYGWSGVNBFEMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(5-氨基-2-氯-苯基)-5-甲基-苯并[1,2,4]三嗪-3-基胺 、 4-溴-N-(2-吡咯烷-1-基乙基)苯磺酰胺 在 tris(dibenzylideneacetone)dipalladium (0) 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 4-[7-(5-amino-2-chloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide
  参考文献：
  名称：

  Discovery of [7-(2,6-dichlorophenyl)-5-methylbenzo [1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]amine—a potent, orally active Src kinase inhibitor with anti-tumor activity in preclinical assays

  摘要：

  We describe the identification of [7-(2,6-dichlorophenyl)-5-methylbenzo [1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-l-ylethoxy)phenyl]amine (3), a potent, orally active Src inhibitor with desirable PK properties, demonstrated activity in human tumor cell lines and in animal models of tumor growth. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.006
• 作为产物：
  描述：

  4-溴-2-甲基-6-硝基苯胺 在 镍 盐酸 、 sodium hydroxide 、 四(三苯基膦)钯 、 氢气 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 9.0h， 生成 7-(5-氨基-2-氯-苯基)-5-甲基-苯并[1,2,4]三嗪-3-基胺
  参考文献：
  名称：

  Discovery of [7-(2,6-dichlorophenyl)-5-methylbenzo [1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]amine—a potent, orally active Src kinase inhibitor with anti-tumor activity in preclinical assays

  摘要：

  We describe the identification of [7-(2,6-dichlorophenyl)-5-methylbenzo [1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-l-ylethoxy)phenyl]amine (3), a potent, orally active Src inhibitor with desirable PK properties, demonstrated activity in human tumor cell lines and in animal models of tumor growth. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.006

文献信息

• The design and preliminary structure–activity relationship studies of benzotriazines as potent inhibitors of Abl and Abl-T315I enzymes
  作者：Jianguo Cao、Richard Fine、Colleen Gritzen、John Hood、Xinshan Kang、Boris Klebansky、Dan Lohse、Chi Ching Mak、Andrew McPherson、Glenn Noronha、Moorthy S.S. Palanki、Ved P. Pathak、Joel Renick、Richard Soll、Binqi Zeng、Hong Zhu

  DOI：10.1016/j.bmcl.2007.08.043

  日期：2007.11

  We describe the design, synthesis and structure-activity relationship studies in optimizing a series of benzotriazine compounds as potent inhibitors of both Abl and Abl-T315I enzymes. The design includes targeting of an acid functional residue on the alpha C-helix that is available only upon kinase activation. This designed interaction provides an advantage in overcoming the challenges arising from the T315I mutation of Abl and transforms poor (ca. 10 mu M) inhibitors into those with low nM potency. (c) 2007 Elsevier Ltd. All rights reserved.