2-Tert-butyl-1-(cyclopropylmethyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine | 1185288-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-Tert-butyl-1-(cyclopropylmethyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine
• CAS: 1185288-83-8
• 化学式: C₁₄H₂₃N₃
• 分子量: 233.357
• InChiKey: MPUMJFRWGJDKHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲氧基-1-乙基磺酰氯 、 2-Tert-butyl-1-(cyclopropylmethyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 C₁₇H₂₉N₃O₃S
  参考文献：
  名称：

  Rapid assessment of a novel series of selective CB2 agonists using parallel synthesis protocols: A Lipophilic Efficiency (LipE) analysis

  摘要：

  A series of libraries were designed using the 1-(cyclopropylmethyl)-2-alkyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c] pyridin-5-ium templates 2a-b, and Sulfonamide derivatives 11a-n proved to be potent agonists of the CB2 receptor. Analysis of the Lipophilic Efficiency (LipE) of potent compounds provided new insight for the design of potent, metabolically stable CB2 agonists. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.062
• 作为产物：
  描述：

  在 platinum(IV) oxide 、 氢气 作用下， 以 溶剂黄146 为溶剂， 50.0 ℃ 、344.75 kPa 条件下， 反应 72.0h， 生成 2-Tert-butyl-1-(cyclopropylmethyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine
  参考文献：
  名称：

  Rapid assessment of a novel series of selective CB2 agonists using parallel synthesis protocols: A Lipophilic Efficiency (LipE) analysis

  摘要：

  A series of libraries were designed using the 1-(cyclopropylmethyl)-2-alkyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c] pyridin-5-ium templates 2a-b, and Sulfonamide derivatives 11a-n proved to be potent agonists of the CB2 receptor. Analysis of the Lipophilic Efficiency (LipE) of potent compounds provided new insight for the design of potent, metabolically stable CB2 agonists. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.062

文献信息

• Identification of a Chemical Probe for Family VIII Bromodomains through Optimization of a Fragment Hit
  作者：Brian S. Gerstenberger、John D. Trzupek、Cynthia Tallant、Oleg Fedorov、Panagis Filippakopoulos、Paul E. Brennan、Vita Fedele、Sarah Martin、Sarah Picaud、Catherine Rogers、Mihir Parikh、Alexandria Taylor、Brian Samas、Alison O’Mahony、Ellen Berg、Gabriel Pallares、Adam D. Torrey、Daniel K. Treiber、Ivan J. Samardjiev、Brian T. Nasipak、Teresita Padilla-Benavides、Qiong Wu、Anthony N. Imbalzano、Jeffrey A. Nickerson、Mark E. Bunnage、Susanne Müller、Stefan Knapp、Dafydd R. Owen

  DOI：10.1021/acs.jmedchem.6b00012

  日期：2016.5.26

  modules. Here we report the discovery of the potent, acetyl-lysine-competitive, and cell active inhibitor PFI-3 that binds to certain family VIII bromodomains while displaying significant, broader bromodomain family selectivity. The high specificity of PFI-3 for family VIII was achieved through a novel bromodomain binding mode of a phenolic headgroup that led to the unusual displacement of water molecules

  在选定的组蛋白赖氨酸残基上的染色质的乙酰基翻译后修饰是通过与溴结构域阅读器模块的乙酰基赖氨酸特异性相互作用来解释的。在这里，我们报告发现一种有效的，与乙酰赖氨酸竞争的，具有细胞活性的抑制剂PFI-3，该抑制剂与某些VIII族溴结构域结合，同时显示出显着的，更广泛的溴结构域家族选择性。PFI-3对VIII族的高特异性是通过酚类头基的新型溴结构域结合模式实现的，该模式导致水分子异常移位，而水分子通常被迄今报道的大多数其他溴结构域抑制剂保留。详细描述了从最初的片段筛选击中导致PFI-3的药物化学程序，还报道了具有不同的VIII族溴结构域选择性分布的其他类似物。我们还描述了作为化学探针的PFI-3的完整药理特性，以及脂肪细胞和成肌细胞分化试验的表型数据。
• Rapid assessment of a novel series of selective CB2 agonists using parallel synthesis protocols: A Lipophilic Efficiency (LipE) analysis
  作者：Thomas Ryckmans、Martin P. Edwards、Val A. Horne、Ana Monica Correia、Dafydd R. Owen、Lisa R. Thompson、Isabelle Tran、Michelle F. Tutt、Tim Young

  DOI：10.1016/j.bmcl.2009.05.062

  日期：2009.8

  A series of libraries were designed using the 1-(cyclopropylmethyl)-2-alkyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c] pyridin-5-ium templates 2a-b, and Sulfonamide derivatives 11a-n proved to be potent agonists of the CB2 receptor. Analysis of the Lipophilic Efficiency (LipE) of potent compounds provided new insight for the design of potent, metabolically stable CB2 agonists. (C) 2009 Elsevier Ltd. All rights reserved.