4-(1-cyclohexyl-1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine | 908590-49-8

• 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-cyclohexyl-1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine
• 英文别名: 4-(1-cyclohexylbenzimidazol-2-yl)-1,2,5-oxadiazol-3-amine
• CAS: 908590-49-8
• 化学式: C₁₅H₁₇N₅O
• 分子量: 283.333
• InChiKey: BCODCVMBVICQAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  N-(2-氨基苯基)-n-环己胺 、 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-cyclohexyl-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

• Medicaments
  申请人：Alberti John Michael

  公开号：US20050153978A1

  公开（公告）日：2005-07-14

  A method of treating an Msk-1 and/or ROCK(1 and 2) mediated disease or condition in a mammal comprising administration of an effective amount of a compounds of the formula (I) and physiologically acceptable salts thereof wherein, R 1 is a 5, or 6 membered heterocyclic group selected from group a, b, c or d wherein X 1 is a group selected from N or CR 7 and X 2 is a group selected from O, S or NR 8 ; X 3 and X 4 which may be the same or different is a group selected from N or CR 7 ; X 5 is a group selected from O, S or NR 8 and X 6 is N or CR 7 ; X 7 , X 8 and X 9 may be the same or different and selected from a group N or CR 7 , pharmaceutical compositions, novel compounds and processes for their preparation.

  一种治疗哺乳动物中MSK-1和/或ROCK（1和2）介导的疾病或病况的方法，包括给予化合物(I)及其生理上可接受的盐的有效量，其中，R1是从a、b、c或d组中选择的5个或6个成员的杂环基团，其中X1是选择自N或CR7的基团，X2是选择自O、S或NR8的基团；X3和X4可以相同或不同，是选择自N或CR7的基团；X5是选择自O、S或NR8的基团，X6是N或CR7；X7、X8和X9可以相同或不同，选择自N或CR7的基团；制备这些新化合物的药物组合物和方法。
• BENZIMIDAZOLES AND THEIR USE AS MITOGEN-ACTIVATED- AND RHO-KINASE INHIBITORS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1487441A2

  公开（公告）日：2004-12-22
• [EN] BENZIMIDAZOLES AND THEIR USE AS MITOGEN-ACTIVATED- AND RHO-KINASE INHIBITORS<br/>[FR] MEDICAMENTS
  申请人：GLAXO GROUP LTD

  公开号：WO2003080125A2

  公开（公告）日：2003-10-02

  A method of treating an Msk-1 and/or ROCK(1 and 2) mediated disease or condition in a mammal comprising administration of an effective amount of a compounds of the formula (I) and physiologically acceptable salts thereof wherein, R1 is a 5, or 6 membered heterocyclic group selected from group a, b, c or d wherein X1 is a group selected from N or CR7 and X2 is a group selected from O, S or NR8; X3 and X4 which may be the same or different is a group selected from N or CR7; X5 is a group selected from O, S or NR8 and X6 is N or CR7; X7, X8 and X9 may be the same or different and selected from a group N or CR7, pharmaceutical compositions, novel compounds and processes for their preparation.
• 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.