4-amino-N-isobutyl-1,2,5-oxadiazole-3-carboxamidine | 847150-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: 4-amino-N-isobutyl-1,2,5-oxadiazole-3-carboxamidine
• 英文别名: 4-amino-N'-(2-methylpropyl)-1,2,5-oxadiazole-3-carboximidamide
• CAS: 847150-28-1
• 化学式: C₇H₁₃N₅O
• 分子量: 183.213
• InChiKey: HQPDHBPWAUXJPN-UHFFFAOYSA-N

物化性质

• 沸点：
  295.1±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-N-isobutyl-1,2,5-oxadiazole-3-carboxamidine 、 2-氯丙烯腈 在 二乙基异丙基胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以50%的产率得到2-(4-amino-1,2,5-oxadiazol-3-yl)-1-isobutyl-4,5-dihydro-1H-imidazole-4-carbonitrile
  参考文献：
  名称：

  4-(Benzimidazol-2-yl)-1,2,5-oxadiazol-3-ylamine derivatives: Potent and selective p70S6 kinase inhibitors

  摘要：

  We report herein the design and synthesis of 4-(benzimidazol-2-yl)-1,2,5-oxadiazol-3-amine derivatives as inhibitors of p70S6 kinase. Screening hits containing the 4-(benzimidazol-2-yl)-1,2,5-oxadiazol-3-ylamine scaffold were optimized for p70S6K potency and selectivity against related kinases. Structure-based design employing an active site homology model derived from PKA led to the preparation of benzimidazole 5-substituted compounds 26 and 27 as highly potent inhibitors (K-i < 1 nM) of p70S6K, with > 100-fold selectivity against PKA, ROCK and GSK3. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.022
• 作为产物：
  描述：

  异丁胺 、 4-氨基-1,2,5-噁二唑-3-甲腈 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以68%的产率得到4-amino-N-isobutyl-1,2,5-oxadiazole-3-carboxamidine
  参考文献：
  名称：

  4-(Benzimidazol-2-yl)-1,2,5-oxadiazol-3-ylamine derivatives: Potent and selective p70S6 kinase inhibitors

  摘要：

  We report herein the design and synthesis of 4-(benzimidazol-2-yl)-1,2,5-oxadiazol-3-amine derivatives as inhibitors of p70S6 kinase. Screening hits containing the 4-(benzimidazol-2-yl)-1,2,5-oxadiazol-3-ylamine scaffold were optimized for p70S6K potency and selectivity against related kinases. Structure-based design employing an active site homology model derived from PKA led to the preparation of benzimidazole 5-substituted compounds 26 and 27 as highly potent inhibitors (K-i < 1 nM) of p70S6K, with > 100-fold selectivity against PKA, ROCK and GSK3. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.022

文献信息

• Aminofurazan compounds useful as protein kinase inhibitors
  申请人：Come H. Jon

  公开号：US20050148640A1

  公开（公告）日：2005-07-07

  The present invention relates to compounds useful of inhibitors of protein kinases. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various disease, conditions, or disorders.

  本发明涉及一种有用的蛋白激酶抑制剂化合物。本发明还提供了包括上述化合物的药学上可接受的组合物，并提供了使用这些组合物治疗各种疾病、病况或障碍的方法。
• [EN] (4 -AMINO -1,2, 5-OXADIAZOL-4-YL) -HET?ROAROMATIC COMPOUNDS USEFUL AS PROTEIN KINASE INHIBITORS<br/>[FR] COMPOSES D'AMINOFURAZAN UTILES COMME INHIBITEURS DE PROTEINE-KINASES
  申请人：VERTEX PHARMA

  公开号：WO2005019190A3

  公开（公告）日：2007-09-20
• 2-(4-AMINO-1,2,5-OXADIAZOL-4-YL)-IMIDAZOLE COMPOUNDS USEFUL AS PROTEIN KINASE INHIBITORS
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP1660467B1

  公开（公告）日：2011-12-07
• AMINOFURAZAN COMPOUNDS AS PROTEIN KINASE INHIBITORS
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP1660467A2

  公开（公告）日：2006-05-31
• US7157476B2
  申请人：——

  公开号：US7157476B2

  公开（公告）日：2007-01-02