ethyl 3-(2,6-dichlorophenyl)-1-methyl-1H-pyrazole-4-carboxylate | 1245094-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-(2,6-dichlorophenyl)-1-methyl-1H-pyrazole-4-carboxylate
• 英文别名: Ethyl 3-(2,6-dichlorophenyl)-1-methylpyrazole-4-carboxylate；ethyl 3-(2,6-dichlorophenyl)-1-methylpyrazole-4-carboxylate
• CAS: 1245094-63-6
• 化学式: C₁₃H₁₂Cl₂N₂O₂
• 分子量: 299.156
• InChiKey: SWTIRARVPQSCIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2,6-dichlorophenyl)-1-methyl-1H-pyrazole-4-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 以46%的产率得到3-(2,6-dichlorophenyl)-1-methyl-1H-pyrazol-4-amine
  参考文献：
  名称：

  Discovery of Potent and Selective Pyrazolopyrimidine Janus Kinase 2 Inhibitors

  摘要：

  The discovery of somatic Jak2 mutations in patients with chronic myeloproliferative neoplasms has led to significant interest in disc-ova-ring selective Jak2 inhibitors for use in treating these disorders. A high-throughput screening effort identified the pyrazolo[1,5-a]pyrimidine scaffold as a potent inhibit-or of Jak2. Optimization of lead compounds 7a-b and 8 in this chemical series for activity against Jak2, selectivity against other Jak family kinases, and good in vivo pharmacokinetic properties led to the discovery of 7j. In a SET2 xenograft model that is dependent on Jak2 for growth, 7j demonstrated a time-dependent knock-down of pSTAT5, a downstream target of Jak2.

  DOI：

  10.1021/jm3012239
• 作为产物：
  描述：

  2,6-二氯苯甲酰氯 在 溶剂黄146 、 三乙胺 、 magnesium chloride 作用下， 以 乙腈 为溶剂， 反应 77.5h， 生成 ethyl 3-(2,6-dichlorophenyl)-1-methyl-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Discovery of Potent and Selective Pyrazolopyrimidine Janus Kinase 2 Inhibitors

  摘要：

  The discovery of somatic Jak2 mutations in patients with chronic myeloproliferative neoplasms has led to significant interest in disc-ova-ring selective Jak2 inhibitors for use in treating these disorders. A high-throughput screening effort identified the pyrazolo[1,5-a]pyrimidine scaffold as a potent inhibit-or of Jak2. Optimization of lead compounds 7a-b and 8 in this chemical series for activity against Jak2, selectivity against other Jak family kinases, and good in vivo pharmacokinetic properties led to the discovery of 7j. In a SET2 xenograft model that is dependent on Jak2 for growth, 7j demonstrated a time-dependent knock-down of pSTAT5, a downstream target of Jak2.

  DOI：

  10.1021/jm3012239