2-(imidazo[1,2-a]pyrazin-3-yl)acetamide | 603309-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡嗪类
• 英文名称: 2-(imidazo[1,2-a]pyrazin-3-yl)acetamide
• 英文别名: 2-Imidazo[1,2-a]pyrazin-3-ylacetamide
• CAS: 603309-31-5
• 化学式: C₈H₈N₄O
• 分子量: 176.178
• InChiKey: VHBGXFJNPRKPHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(imidazo[1,2-a]pyrazin-3-yl)acetamide 在 盐酸 、 potassium tert-butylate 、 乙硫醇 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(1,10-Diazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-3-yl)-4-imidazo[1,2-a]pyrazin-3-ylpyrrole-2,5-dione
  参考文献：
  名称：

  The development of potent and selective bisarylmaleimide GSK3 inhibitors

  摘要：

  Many 3-aryl-4-(1,2,3,4-tetrahydro[1,4]diazepino[6,7,1-hi]indol-7-yl)maleimides exhibit potent GSK3 inhibitory activity (<100 nM IC50), although few show significant selectivity (>100x) versus CDK2, CDK4, or PKCbetaII. However, combining 3-(imidazo[1,2-a]pyridin-3-yl), 3-(pyrazolo[1,5-a]pyridin-3-yl) or aza-analogs with a 4-(2-acyl-(1,2,3,4-tetrahydro[1,4]diazepino[6,7,1-hi]indol-7-yl)) group on the maleimide resulted in very potent inhibitors of GSK3 (less than or equal to5 nM) with >160 to >10,000-fold selectivity versus CDK2/4 and PKCbetaII, These compounds also inhibited tau phosphorylation in cells and were effective in lowering plasma glucose in a rat model of type 2 diabetes (ZDF rat). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.063
• 作为产物：
  描述：

  Imidazo[1,2-a]pyrazin-3-yl-acetic acid ethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 生成 2-(imidazo[1,2-a]pyrazin-3-yl)acetamide
  参考文献：
  名称：

  The development of potent and selective bisarylmaleimide GSK3 inhibitors

  摘要：

  Many 3-aryl-4-(1,2,3,4-tetrahydro[1,4]diazepino[6,7,1-hi]indol-7-yl)maleimides exhibit potent GSK3 inhibitory activity (<100 nM IC50), although few show significant selectivity (>100x) versus CDK2, CDK4, or PKCbetaII. However, combining 3-(imidazo[1,2-a]pyridin-3-yl), 3-(pyrazolo[1,5-a]pyridin-3-yl) or aza-analogs with a 4-(2-acyl-(1,2,3,4-tetrahydro[1,4]diazepino[6,7,1-hi]indol-7-yl)) group on the maleimide resulted in very potent inhibitors of GSK3 (less than or equal to5 nM) with >160 to >10,000-fold selectivity versus CDK2/4 and PKCbetaII, These compounds also inhibited tau phosphorylation in cells and were effective in lowering plasma glucose in a rat model of type 2 diabetes (ZDF rat). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.063

文献信息

• PURINE DERIVATIVES AS KINASE INHIBITORS
  申请人：Engler Thomas Albert

  公开号：US20090105229A1

  公开（公告）日：2009-04-23

  The present invention provides kinase inhibitors of Formula I.

  本发明提供了化合物I的激酶抑制剂。
• US8058425B2
  申请人：——

  公开号：US8058425B2

  公开（公告）日：2011-11-15
• US8022065B2
  申请人：——

  公开号：US8022065B2

  公开（公告）日：2011-09-20
• The development of potent and selective bisarylmaleimide GSK3 inhibitors
  作者：Thomas A. Engler、Sushant Malhotra、Timothy P. Burkholder、James R. Henry、David Mendel、Warren J. Porter、Kelly Furness、Clive Diefenbacher、Angela Marquart、Jon K. Reel、Yihong Li、Joshua Clayton、Brian Cunningham、Johnathan McLean、John C. O’Toole、Joseph Brozinick、Eric Hawkins、Elizabeth Misener、Daniel Briere、Richard A. Brier、Jill R. Wagner、Robert M. Campbell、Bryan D. Anderson、Renee Vaughn、Donald B. Bennett、Timothy I. Meier、James A. Cook

  DOI：10.1016/j.bmcl.2004.12.063

  日期：2005.2

  Many 3-aryl-4-(1,2,3,4-tetrahydro[1,4]diazepino[6,7,1-hi]indol-7-yl)maleimides exhibit potent GSK3 inhibitory activity (<100 nM IC50), although few show significant selectivity (>100x) versus CDK2, CDK4, or PKCbetaII. However, combining 3-(imidazo[1,2-a]pyridin-3-yl), 3-(pyrazolo[1,5-a]pyridin-3-yl) or aza-analogs with a 4-(2-acyl-(1,2,3,4-tetrahydro[1,4]diazepino[6,7,1-hi]indol-7-yl)) group on the maleimide resulted in very potent inhibitors of GSK3 (less than or equal to5 nM) with >160 to >10,000-fold selectivity versus CDK2/4 and PKCbetaII, These compounds also inhibited tau phosphorylation in cells and were effective in lowering plasma glucose in a rat model of type 2 diabetes (ZDF rat). (C) 2005 Elsevier Ltd. All rights reserved.