7-Bromo-5-fluoro-[1,2,4]triazolo[1,5-A]pyridin-2-amine | 1398504-18-1

• 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: 7-Bromo-5-fluoro-[1,2,4]triazolo[1,5-A]pyridin-2-amine
• 英文别名: 7-bromo-5-fluoro-[1,2,4]triazolo[1,5-a]pyridin-2-amine
• CAS: 1398504-18-1
• 化学式: C₆H₄BrFN₄
• 分子量: 231.027
• InChiKey: CFYZGYMMOWDWJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(tert-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide 、 7-Bromo-5-fluoro-[1,2,4]triazolo[1,5-A]pyridin-2-amine 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 5-(2-amino-5-fluoro-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-tert-butylpyridine-3-sulfonamide
  参考文献：
  名称：

  Discovery of 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(tert-butyl)pyridine-3-sulfonamide (CZC24758), as a potent, orally bioavailable and selective inhibitor of PI3K for the treatment of inflammatory disease

  摘要：

  Herein, we disclose the discovery of a series of 7-substituted triazolopyridines which culminated in the identification of 14 (CZC24758), a potent, orally bioavailable small-molecule inhibitor of PI3K gamma, an attractive drug target for inflammatory and autoimmune disorders. Compound 14 has excellent selectivity across the kinome, demonstrates good potency in cell based assays and furthermore exhibits in vivo efficacy in a collagen induced arthritis model in mouse after oral dosing. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.090
• 作为产物：
  描述：

  4-bromo-6-fluoropyridin-2-amine 在 盐酸羟胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 7-Bromo-5-fluoro-[1,2,4]triazolo[1,5-A]pyridin-2-amine
  参考文献：
  名称：

  Discovery of 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(tert-butyl)pyridine-3-sulfonamide (CZC24758), as a potent, orally bioavailable and selective inhibitor of PI3K for the treatment of inflammatory disease

  摘要：

  Herein, we disclose the discovery of a series of 7-substituted triazolopyridines which culminated in the identification of 14 (CZC24758), a potent, orally bioavailable small-molecule inhibitor of PI3K gamma, an attractive drug target for inflammatory and autoimmune disorders. Compound 14 has excellent selectivity across the kinome, demonstrates good potency in cell based assays and furthermore exhibits in vivo efficacy in a collagen induced arthritis model in mouse after oral dosing. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.090

文献信息

• Discovery of 5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(tert-butyl)pyridine-3-sulfonamide (CZC24758), as a potent, orally bioavailable and selective inhibitor of PI3K for the treatment of inflammatory disease
  作者：Mihiro Sunose、Kathryn Bell、Katie Ellard、Giovanna Bergamini、Gitte Neubauer、Thilo Werner、Nigel Ramsden

  DOI：10.1016/j.bmcl.2012.05.090

  日期：2012.7

  Herein, we disclose the discovery of a series of 7-substituted triazolopyridines which culminated in the identification of 14 (CZC24758), a potent, orally bioavailable small-molecule inhibitor of PI3K gamma, an attractive drug target for inflammatory and autoimmune disorders. Compound 14 has excellent selectivity across the kinome, demonstrates good potency in cell based assays and furthermore exhibits in vivo efficacy in a collagen induced arthritis model in mouse after oral dosing. (C) 2012 Elsevier Ltd. All rights reserved.