N-(6-isopropoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)isonicotinamide

• 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: N-(6-isopropoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)isonicotinamide
• 英文别名: N-(1,3-dimethyl-2-oxo-6-propan-2-yloxybenzimidazol-5-yl)pyridine-4-carboxamide
• 化学式: C₁₈H₂₀N₄O₃
• 分子量: 340.382
• InChiKey: MWDDVHYAUYJQMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 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 、 sodium hydride 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 2-甲基四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 27.33h， 生成 N-(6-isopropoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)isonicotinamide
  参考文献：
  名称：

  GSK6853, a Chemical Probe for Inhibition 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. 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.

  DOI：

  10.1021/acsmedchemlett.6b00092

文献信息

• 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.