(4-tert-butylphenyl)-(4-chlorophthalazin-1-yl)amine | 866758-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (4-tert-butylphenyl)-(4-chlorophthalazin-1-yl)amine
• 英文别名: N-(4-tert-butylphenyl)-4-chlorophthalazin-1-amine
• CAS: 866758-54-5
• 化学式: C₁₈H₁₈ClN₃
• 分子量: 311.814
• InChiKey: KFKWMCYJOZFRII-UHFFFAOYSA-N

物化性质

• 沸点：
  488.2±40.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.81
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4-tert-butylphenyl)-(4-chlorophthalazin-1-yl)amine 、 3-氨基甲酰基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 3-(4-(4-Tert-butylphenylamino)phthalazin-1-yl)benzamide
  参考文献：
  名称：

  Arylphthalazines as potent, and orally bioavailable inhibitors of VEGFR-2

  摘要：

  A series of arylphthalazine derivatives were synthesized and evaluated as antagonists of VEGF receptor II (VEGFR-2). IM-094482 57, which was prepared in two steps from commercially available starting materials, was found to be a potent inhibitor of VEGFR-2 in enzymatic, cellular and mitogenic assays (comparable activity to ZD-6474). Additionally, 57 inhibited the related receptor, VEGF receptor I (VEGFR-1), and showed excellent exposure when dosed orally to female CD-1 mice. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.049
• 作为产物：
  描述：

  1,4-二氯酞嗪 、 4-叔丁基苯胺 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 48.0h， 以96%的产率得到(4-tert-butylphenyl)-(4-chlorophthalazin-1-yl)amine
  参考文献：
  名称：

  Arylphthalazines as potent, and orally bioavailable inhibitors of VEGFR-2

  摘要：

  A series of arylphthalazine derivatives were synthesized and evaluated as antagonists of VEGF receptor II (VEGFR-2). IM-094482 57, which was prepared in two steps from commercially available starting materials, was found to be a potent inhibitor of VEGFR-2 in enzymatic, cellular and mitogenic assays (comparable activity to ZD-6474). Additionally, 57 inhibited the related receptor, VEGF receptor I (VEGFR-1), and showed excellent exposure when dosed orally to female CD-1 mice. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.049

文献信息

• Arylphthalazines: Identification of a new phthalazine chemotype as inhibitors of VEGFR kinase
  作者：Evgueni L. Piatnitski、Matthew A.J. Duncton、Alexander S. Kiselyov、Reeti Katoch-Rouse、Dan Sherman、Daniel L. Milligan、Chris Balagtas、Wai C. Wong、Joel Kawakami、Jacqueline F. Doody

  DOI：10.1016/j.bmcl.2005.07.064

  日期：2005.11

  A novel class of 4-arylamino-phthalazin-1-yl-benzamides is described as inhibitors of vascular endothelial growth factor receptor II (VEGFR-2). Several compounds display potent VEGFR-2 inhibitory activity with an IC50 as low as 0.078 mu M in an HTRF enzymatic assay. These compounds are relatively selective against a small kinase panel. (c) 2005 Elsevier Ltd. All rights reserved.
• Arylphthalazines. Part 2: 1-(Isoquinolin-5-yl)-4-arylamino phthalazines as potent inhibitors of VEGF receptors I and II
  作者：Matthew A.J. Duncton、Evgueni L. Piatnitski、Reeti Katoch-Rouse、Leon M. Smith、Alexander S. Kiselyov、Daniel L. Milligan、Chris Balagtas、Wai C. Wong、Joel Kawakami、Jacqueline F. Doody

  DOI：10.1016/j.bmcl.2005.12.045

  日期：2006.3

  A novel class of 1-(isoquinolin-5-yl)-4-arylamino-phthalazines is described as inhibitors of vascular endothelial growth factor receptor II (VEGFR-2). Many compounds display VEGFR-2 inhibitory activity with an IC50 as low as 0.017 mu M in an HTRF enzymatic assay. The compounds also inhibit VEGFR-1, a related tyrosine kinase. (C) 2005 Elsevier Ltd. All rights reserved.