4-(1-cyclobutyl-1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine | 1190631-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-(1-cyclobutyl-1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine
• 英文别名: 4-(1-cyclobutylbenzimidazol-2-yl)-1,2,5-oxadiazol-3-amine
• CAS: 1190631-13-0
• 化学式: C₁₃H₁₃N₅O
• 分子量: 255.279
• InChiKey: YOPFBPOFMONRKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N1-cyclobutylbenzene-1,2-diamine 、 甲基4-氨基-1,2,5-恶二唑-3-甲亚氨酸酯 以 溶剂黄146 为溶剂， 反应 0.25h， 生成 4-(1-cyclobutyl-1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine
  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

• 4-(Benzimidazol-2-yl)-1,2,5-oxadiazol-3-ylamine derivatives: Potent and selective p70S6 kinase inhibitors
  作者：Upul Bandarage、Brian Hare、Jonathan Parsons、Ly Pham、Craig Marhefka、Guy Bemis、Qing Tang、Cameron Stuver Moody、Steve Rodems、Sundeep Shah、Chris Adams、Jose Bravo、Emmanuelle Charonnet、Vladimir Savic、Jon H. Come、Jeremy Green

  DOI：10.1016/j.bmcl.2009.07.022

  日期：2009.9

  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.