N-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine | 1257709-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: N-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine
• CAS: 1257709-83-3
• 化学式: C₁₃H₁₂N₄O
• 分子量: 240.264
• InChiKey: BVDSMDDCKWSQFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine 、 4-（甲磺酰基）苯硼酸 在 palladium diacetate 、 sodium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 [8-(4-methanesulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-methoxyphenyl)amine
  参考文献：
  名称：

  A Selective, Orally Bioavailable 1,2,4-Triazolo[1,5-a]pyridine-Based Inhibitor of Janus Kinase 2 for Use in Anticancer Therapy: Discovery of CEP-33779

  摘要：

  Members of the JAK family of nonreceptor tyrosine kinases play a critical role in the growth and progression of many cancers and in inflammatory diseases. JAK2 has emerged as a leading therapeutic target for oncology, providing a rationale for the development of a selective JAK2 inhibitor. A program to optimize selective JAK2 inhibitors to combat cancer while reducing the risk of immune suppression associated with JAK3 inhibition was undertaken. The structure-activity relationships and biological evaluation of a novel series of compounds based on a 1,2,4-triazolo[1,5-a]pyridine scaffold are reported. Para substitution on the aryl at the C8 position of the core was optimum for JAK2 potency (17). Substitution at the C2 nitrogen position was required for cell potency (21). Interestingly, meta substitution of C2-NH-aryl moiety provided exceptional selectivity for JAK2 over JAK3 (23). These efforts led to the discovery of CEP-33779 (29), a novel, selective, and orally bioavailable inhibitor of JAK2.

  DOI：

  10.1021/jm300248q