[8-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methylpiperazin-1-yl)phenyl]amine | 1257709-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: [8-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methylpiperazin-1-yl)phenyl]amine
• 英文别名: [8-(4-Fluoro-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine；8-(4-fluorophenyl)-N-[3-(4-methylpiperazin-1-yl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine
• CAS: 1257709-19-5
• 化学式: C₂₃H₂₃FN₆
• 分子量: 402.474
• InChiKey: DRBLSGJGTGHHCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  48.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(3-溴苯基)-4-甲基-哌嗪 、 8-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-ylamine 在 palladium diacetate 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 [8-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methylpiperazin-1-yl)phenyl]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

文献信息

• Preparation and Uses of 1,2,4-Triazolo [1,5a] Pyridine Derivatives
  申请人：Cephalon, Inc.

  公开号：US20130296312A1

  公开（公告）日：2013-11-07

  This application relates, in part, to compounds of the general Formula I and/or salts thereof, wherein X, R 1A , R 1B , R 2 , R 3 , R 4 , and R 5 are as defined herein. The application also relates to compositions and methods of inhibiting at least JAK2 in subjects in recognized need thereof for the treatment of diseases or disorders for which inhibition of at least JAK2 is indicated.

  该应用程序部分涉及一般式I化合物和/或其盐，其中X、R1A、R1B、R2、R3、R4和R5的定义如本文所述。该应用程序还涉及组合物和方法，用于抑制至少在有需要的患者中的JAK2，以治疗需要抑制至少JAK2的疾病或疾病。
• Preparation and uses of 1,2,4-triazolo [1,5a] pyridine derivatives
  申请人：Curry Matthew A.

  公开号：US08501936B2

  公开（公告）日：2013-08-06

  This application relates to compounds of the general Formula I and salts thereof, wherein X, R1A, R1B, R2, R3, R4, and R5 are as defined herein. The application also relates to compositions and methods of treatment of hyperproliferative diseases or disorders.

  本申请涉及一般式I的化合物及其盐，其中X、R1A、R1B、R2、R3、R4和R5的定义如本文所述。本申请还涉及治疗过度增殖性疾病或障碍的组合物和方法。
• PREPARATION AND USES OF 1,2,4-TRIAZOLO [1,5a]PYRIDINE DERIVATIVES
  申请人：Cephalon, Inc.

  公开号：EP2438066A2

  公开（公告）日：2012-04-11
• US8501936B2
  申请人：——

  公开号：US8501936B2

  公开（公告）日：2013-08-06
• US8633173B2
  申请人：——

  公开号：US8633173B2

  公开（公告）日：2014-01-21