6-(4-nitrophenyl)-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine | 1021870-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-(4-nitrophenyl)-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine
• CAS: 1021870-86-9
• 化学式: C₁₈H₁₃N₅O₂
• 分子量: 331.334
• InChiKey: LHHYDDAANFJUFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(4-nitrophenyl)-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine 在 盐酸 、 tin(ll) chloride 作用下， 以 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 C₁₈H₁₅N₅
  参考文献：
  名称：

  7-Aminopyrazolo[1,5-a]pyrimidines as Potent Multitargeted Receptor Tyrosine Kinase Inhibitors

  摘要：

  7-Aminopyrazolo[1,5-a]pyrimidine urea receptor tyrosine kinase inhibitors have been discovered. Investigation of structure-activity relationships of the pyrazolo[1,5-a]pyrimidine nucleus led to a series of 6-(4-N,N'-diphenyl)ureas that potently inhibited a panel of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases. Several of these compounds, such as 34a, are potent inhibitors of kinase insert domain-containing receptor tyrosine kinase (KDR) both enzymatically (< 10 nM) and cellularly (< 10 nM). In addition, compound 34a possesses a favorable pharmacokinetic profile and demonstrates efficacy in the estradiol-induced murine uterine edema (UE) model (ED(50) = 1.4 mg/kg).

  DOI：

  10.1021/jm701397k
• 作为产物：
  描述：

  3-amino-4-phenylpyrazole 、 3-dimethylamino-2-(4-nitrophenyl) acrylonitrile 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 6-(4-nitrophenyl)-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine
  参考文献：
  名称：

  7-Aminopyrazolo[1,5-a]pyrimidines as Potent Multitargeted Receptor Tyrosine Kinase Inhibitors

  摘要：

  7-Aminopyrazolo[1,5-a]pyrimidine urea receptor tyrosine kinase inhibitors have been discovered. Investigation of structure-activity relationships of the pyrazolo[1,5-a]pyrimidine nucleus led to a series of 6-(4-N,N'-diphenyl)ureas that potently inhibited a panel of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases. Several of these compounds, such as 34a, are potent inhibitors of kinase insert domain-containing receptor tyrosine kinase (KDR) both enzymatically (< 10 nM) and cellularly (< 10 nM). In addition, compound 34a possesses a favorable pharmacokinetic profile and demonstrates efficacy in the estradiol-induced murine uterine edema (UE) model (ED(50) = 1.4 mg/kg).

  DOI：

  10.1021/jm701397k

文献信息

• Studies with enaminonitriles: Synthesis and chemical reactivity of 2‐phenyl‐3‐piperidin‐1‐yl acrylonitrile under microwave heating
  作者：Abdellatif M. Salaheldin、Maryana K. Alphy

  DOI：10.1002/jhet.5570450202

  日期：2008.3

  Benzyl cyanide reacts with triethylorthoformate and piperidine in DMF solution to yield the title compound 2. This reacted with aromatic amines to yield either aminoacrylonitriles or quinoline depending on reaction conditions and substitution pattern on the aromatic amine. The reaction of compound 2 with hydrazine hydrate could only be effected in the microwave oven and resulted in the formation of

  苄基氰化物在DMF溶液中与原甲酸三乙酯和哌啶反应生成标题化合物2。根据芳族胺的反应条件和取代方式，它与芳族胺反应生成氨基丙烯腈或喹啉。化合物2与水合肼的反应只能在微波炉中进行，导致氨基吡唑7的形成。7的重氮化并与活性亚甲基试剂偶合，得到吡唑并[5,1- c ]-[1,2,4]三嗪衍生物。