N-[4-(3-amino-1,2-benzoxazol-4-yl)phenyl]benzamide | 1012367-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-(3-amino-1,2-benzoxazol-4-yl)phenyl]benzamide
• CAS: 1012367-56-4
• 化学式: C₂₀H₁₅N₃O₂
• 分子量: 329.358
• InChiKey: VLNXUZCOGPVFFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(4-aminophenyl)-1,2-benzoisooxazol-3-amine 、 苯甲酰氯 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以64%的产率得到N-[4-(3-amino-1,2-benzoxazol-4-yl)phenyl]benzamide
  参考文献：
  名称：

  3-Amino-benzo[d]isoxazoles as Novel Multitargeted Inhibitors of Receptor Tyrosine Kinases

  摘要：

  A series of benzoisoxazoles and benzoisothiazoles have been synthesized and evaluated as inhibitors of receptor tyrosine kinases (RTKs). Structure-activity relationship studies led to the identification of 3-amino benzo[d]isoxazoles, incorporating a N,N'-diphenyl urea moiety of the 4-position that potently inhibited both the vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor families of RTKs. Within this series, orally bioavailable compounds possessing promising pharmacokinetic profiles were identified, and a number of compounds demonstrated in vivo efficacy in models of VEGF-stimulated vascular permeability and tumor growth. In particular, compound 50 exhibited an ED50 of 2.0 mg/kg in the VEGF-stimulated uterine edema model and 81% inhibition in the human fibrosarcoma (HT1080) tumor growth model when given orally at a dose of 10 mg/kg/day.

  DOI：

  10.1021/jm701096v

文献信息

• 3-Amino-benzo[<i>d</i>]isoxazoles as Novel Multitargeted Inhibitors of Receptor Tyrosine Kinases
  作者：Zhiqin Ji、Asma A. Ahmed、Daniel H. Albert、Jennifer J. Bouska、Peter F. Bousquet、George, A. Cunha、Gilbert Diaz、Keith B. Glaser、Jun Guo、Christopher M. Harris、Junling Li、Patrick A. Marcotte、Maria D. Moskey、Tetsuro Oie、Lori Pease、Nirupama B. Soni、Kent D. Stewart、Steven K. Davidsen、Michael R. Michaelides

  DOI：10.1021/jm701096v

  日期：2008.3.13

  A series of benzoisoxazoles and benzoisothiazoles have been synthesized and evaluated as inhibitors of receptor tyrosine kinases (RTKs). Structure-activity relationship studies led to the identification of 3-amino benzo[d]isoxazoles, incorporating a N,N'-diphenyl urea moiety of the 4-position that potently inhibited both the vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor families of RTKs. Within this series, orally bioavailable compounds possessing promising pharmacokinetic profiles were identified, and a number of compounds demonstrated in vivo efficacy in models of VEGF-stimulated vascular permeability and tumor growth. In particular, compound 50 exhibited an ED50 of 2.0 mg/kg in the VEGF-stimulated uterine edema model and 81% inhibition in the human fibrosarcoma (HT1080) tumor growth model when given orally at a dose of 10 mg/kg/day.