5-amino-1,3-dimethyl-6-(piperidin-1-yl)-1H-benzo[d]imidazol-2(3H)-one | 878432-74-7

• 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: 5-amino-1,3-dimethyl-6-(piperidin-1-yl)-1H-benzo[d]imidazol-2(3H)-one
• 英文别名: 5-Amino-1,3-dimethyl-6-piperidin-1-yl-1,3-dihydro-benzoimidazol-2-one；5-amino-1,3-dimethyl-6-piperidin-1-ylbenzimidazol-2-one
• CAS: 878432-74-7
• 化学式: C₁₄H₂₀N₄O
• mdl: MFCD07022260
• 分子量: 260.339
• InChiKey: ZOMSUTGXSSYGLG-UHFFFAOYSA-N

物化性质

• 沸点：
  461.2±45.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-amino-1,3-dimethyl-6-(piperidin-1-yl)-1H-benzo[d]imidazol-2(3H)-one 、 甲氧基苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以55%的产率得到N-(1,3-dimethyl-2-oxo-6-(piperidin-1-yl)-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-2-methoxybenzamide
  参考文献：
  名称：

  1,3-Dimethyl Benzimidazolones Are Potent, Selective Inhibitors of the BRPF1 Bromodomain

  摘要：

  The BRPF (bromodomain and PHD finger-containing) protein family are important scaffolding proteins for assembly of MYST histone acetyltransferase complexes. Here, we report the discovery, binding mode, and structureactivity relationship (SAR) of the first potent, selective series of inhibitors of the BRPF1 bromodomain.

  DOI：

  10.1021/ml5002932
• 作为产物：
  描述：

  5-fluoro-1,3-dimethyl-6-nitro-1H-benzo[d]imidazol-2(3H)-one 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 20.0~120.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 5-amino-1,3-dimethyl-6-(piperidin-1-yl)-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  1,3-Dimethyl Benzimidazolones Are Potent, Selective Inhibitors of the BRPF1 Bromodomain

  摘要：

  The BRPF (bromodomain and PHD finger-containing) protein family are important scaffolding proteins for assembly of MYST histone acetyltransferase complexes. Here, we report the discovery, binding mode, and structureactivity relationship (SAR) of the first potent, selective series of inhibitors of the BRPF1 bromodomain.

  DOI：

  10.1021/ml5002932

文献信息

• BIFUNCTION CHEMICAL EPIGENENTIC MODIFIERS AND METHODS OF USE
  申请人：The University of North Carolina at Chapel Hill

  公开号：US20210355476A1

  公开（公告）日：2021-11-18

  The present disclosure relates to bifunctional chemical epigenetic modifiers, and methods of making, kits and using the bifunctional chemical epigenetic modifiers. The bifunctional chemical epigenetic modifiers can include a FK506 molecule or derivative thereof, a linker and a bifunctional ligand. The bifunctional ligand can be a histone deacetylase inhibitor.

  本公开涉及双功能化学表观遗传修饰剂，以及制备方法、工具包和使用双功能化学表观遗传修饰剂的方法。双功能化学表观遗传修饰剂可以包括FK506分子或其衍生物，连接剂和双功能配体。双功能配体可以是组蛋白去乙酰化酶抑制剂。
• 1,3-Dimethyl Benzimidazolones Are Potent, Selective Inhibitors of the BRPF1 Bromodomain
  作者：Emmanuel H. Demont、Paul Bamborough、Chun-wa Chung、Peter D. Craggs、David Fallon、Laurie J. Gordon、Paola Grandi、Clare I. Hobbs、Jameed Hussain、Emma J. Jones、Armelle Le Gall、Anne-Marie Michon、Darren J. Mitchell、Rab K. Prinjha、Andy D. Roberts、Robert J. Sheppard、Robert J. Watson

  DOI：10.1021/ml5002932

  日期：2014.11.13

  The BRPF (bromodomain and PHD finger-containing) protein family are important scaffolding proteins for assembly of MYST histone acetyltransferase complexes. Here, we report the discovery, binding mode, and structureactivity relationship (SAR) of the first potent, selective series of inhibitors of the BRPF1 bromodomain.
• GSK6853, a Chemical Probe for Inhibition of the BRPF1 Bromodomain
  作者：Paul Bamborough、Heather A. Barnett、Isabelle Becher、Mark J. Bird、Chun-wa Chung、Peter D. Craggs、Emmanuel H. Demont、Hawa Diallo、David J. Fallon、Laurie J. Gordon、Paola Grandi、Clare I. Hobbs、Edward Hooper-Greenhill、Emma J. Jones、Robert P. Law、Armelle Le Gall、David Lugo、Anne-Marie Michon、Darren J. Mitchell、Rab K. Prinjha、Robert J. Sheppard、Allan J. B. Watson、Robert J. Watson

  DOI：10.1021/acsmedchemlett.6b00092

  日期：2016.6.9

  The BRPF (Bromodomain and PHD Finger-containing) protein family are important scaffolding proteins for assembly of MYST histone acetyltransferase complexes. A selective benzimidazolone BRPF1 inhibitor showing micro molar activity in a cellular target engagement assay was recently described. Herein, we report the optimization of this series leading to the identification of a superior BRPF1 inhibitor suitable for in vivo studies.