2-{3-[2-(4-amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]propyl}-1H-isoindole-1,3(2H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-{3-[2-(4-amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]propyl}-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[3-[2-(4-amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethylimidazo[4,5-c]pyridin-6-yl]propyl]isoindole-1,3-dione
• 化学式: C₂₁H₁₈ClN₇O₃
• 分子量: 451.872
• InChiKey: UZJJIHKYOPUMHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-{3-[2-(4-amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]propyl}-1H-isoindole-1,3(2H)-dione 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以59%的产率得到2-{3-[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-4-(3-hydroxy-3-methyl-1-butyn-1-yl)-1H-imidazo[4,5-c]pyridin-6-yl]propyl}-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  WO2006/113837

  摘要：

  公开号：
• 作为产物：
  描述：

  4-(6-bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine 、 N-烯丙基邻苯二甲酰亚胺 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 potassium carbonate 、 9-硼双环[3.3.1]壬烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-{3-[2-(4-amino-1,2,5-oxadiazol-3-yl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]propyl}-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Aminofurazans as potent inhibitors of AKT kinase

  摘要：

  AKT inhibitors containing an imidazopyridine aminofurazan scaffold have been optimized. We have previously disclosed identification of the AKT inhibitor GSK690693, which has been evaluated in clinical trials in cancer patients. Herein we describe recent efforts focusing on investigating a distinct region of this scaffold that have afforded compounds (30 and 32) with comparable activity profiles to that of GSK690693.

  DOI：

  10.1016/j.bmcl.2009.01.002

文献信息

• Inhibitors of Akt Activity
  申请人：Heerding Dirk A.

  公开号：US20080318947A1

  公开（公告）日：2008-12-25

  Invented are novel 1H-imidazo[4,5-c]pyridin-2-yl compounds, the use of such compounds as inhibitors of protein kinase B activity and in the treatment of cancer and arthritis.

  本发明涉及一种新型的1H-咪唑并[4,5-c]吡啶-2-基化合物，其作为蛋白激酶B活性的抑制剂以及在癌症和关节炎治疗中的应用。
• WO2006/113837
  申请人：——

  公开号：——

  公开（公告）日：——
• INHIBITORS OF AKT ACTIVITY
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1874768A2

  公开（公告）日：2008-01-09
• [EN] INHIBITORS OF AKT ACTIVITY<br/>[FR] INHIBITEURS DE L'ACTIVITE AKT
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2006113837A2

  公开（公告）日：2006-10-26

  [EN] Invented are novel 1 H-imidazo[4,5-c]pyridin-2-yl compounds, the use of such compounds as inhibitors of protein kinase B activity and in the treatment of cancer and arthritis.
  [FR] L'invention se rapporte à de nouveaux composés 1H-imidazo[4,5-c]pyridin-2-yle, à l'utilisation de ces composés en tant qu'inhibiteurs de l'activité des protéines kinase B et pour le traitement du cancer et de l'arthrite.
• Aminofurazans as potent inhibitors of AKT kinase
  作者：Meagan B. Rouse、Mark A. Seefeld、Jack D. Leber、Kenneth C. McNulty、Lihui Sun、William H. Miller、ShuYun Zhang、Elisabeth A. Minthorn、Nestor O. Concha、Anthony E. Choudhry、Michael D. Schaber、Dirk A. Heerding

  DOI：10.1016/j.bmcl.2009.01.002

  日期：2009.3

  AKT inhibitors containing an imidazopyridine aminofurazan scaffold have been optimized. We have previously disclosed identification of the AKT inhibitor GSK690693, which has been evaluated in clinical trials in cancer patients. Herein we describe recent efforts focusing on investigating a distinct region of this scaffold that have afforded compounds (30 and 32) with comparable activity profiles to that of GSK690693.