N-[4-(3-氨基苯并[d]异恶唑-4-基)苯基]-3-(3-三氟甲基苯基)丙烯酰胺 | 1012367-57-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: N-[4-(3-氨基苯并[d]异恶唑-4-基)苯基]-3-(3-三氟甲基苯基)丙烯酰胺
• 英文名称: N-[4-(3-aminobenzo[d]isoxazol-4-yl)phenyl]-3-(3-trifluoromethylphenyl)acrylamide
• 英文别名: (2E)-N-[4-(3-amino-1,2-benzoxazol-4-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]prop-2-enamide；(E)-N-[4-(3-amino-1,2-benzoxazol-4-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]prop-2-enamide
• CAS: 1012367-57-5
• 化学式: C₂₃H₁₆F₃N₃O₂
• 分子量: 423.394
• InChiKey: PYKWUFWGJLDSGF-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  81.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(4-aminophenyl)-1,2-benzoisooxazol-3-amine 、 (2E)-3-[3-(三氟甲基)苯基]丙烯酰氯 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-[4-(3-氨基苯并[d]异恶唑-4-基)苯基]-3-(3-三氟甲基苯基)丙烯酰胺
  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