(4-((5,6-dichloro-2-methyl-4-nitro-1H-benzo[d]imidazol-1-yl)-methyl)phenyl)boronic acid

• 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-((5,6-dichloro-2-methyl-4-nitro-1H-benzo[d]imidazol-1-yl)-methyl)phenyl)boronic acid
• 英文别名: (4-((5,6-dichloro-2-methyl-4-nitro-1H-benzo[d]imidazol-1-yl)methyl)phenyl)boronic acid；(4-((5,6-Dichloro-2-methyl-4-nitro-1H-benzo[d]imidazol-1-yl)methyl)phenyl)boronic acid；[4-[(5,6-dichloro-2-methyl-4-nitrobenzimidazol-1-yl)methyl]phenyl]boronic acid
• 化学式: C₁₅H₁₂BCl₂N₃O₄
• 分子量: 379.995
• InChiKey: BAQJLICUXUZTMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-甲基亚氨二乙酸 、 (4-((5,6-dichloro-2-methyl-4-nitro-1H-benzo[d]imidazol-1-yl)-methyl)phenyl)boronic acid 在 magnesium sulfate 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 1.0h， 以89%的产率得到2-(4-((5,6-dichloro-2-methyl-4-nitro-1H-benzo[d]-imidazol-1-yl)methyl)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
  参考文献：
  名称：

  Discovery of the First Potent and Selective Inhibitors of Human dCTP Pyrophosphatase 1

  摘要：

  The dCTPase pyrophosphatase 1 (dCTPase) regulates the intracellular nucleotide pool through hydrolytic degradation of canonical and noncanonical nucleotide triphosphates (dNTPs). dCTPase is highly expressed in multiple carcinomas and is associated with cancer cell sternness. Here we report on the development of the first potent and selective dCTPase inhibitors that enhance the cytotoxic effect of cytidine analogues in leukemia cells. Boronate 30 displays a promising in vitro ADME profile, including plasma and mouse microsomal half-lives, aqueous solubility, cell permeability and CYP inhibition, deeming it a suitable compound for in vivo studies.

  DOI：

  10.1021/acs.jmedchem.5b01741
• 作为产物：
  描述：

  5,6-二氯-2-甲基苯并咪唑 在 硝酸 、 potassium carbonate 作用下， 以 甲基叔丁基醚 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 33.0h， 生成 (4-((5,6-dichloro-2-methyl-4-nitro-1H-benzo[d]imidazol-1-yl)-methyl)phenyl)boronic acid
  参考文献：
  名称：

  Discovery of the First Potent and Selective Inhibitors of Human dCTP Pyrophosphatase 1

  摘要：

  The dCTPase pyrophosphatase 1 (dCTPase) regulates the intracellular nucleotide pool through hydrolytic degradation of canonical and noncanonical nucleotide triphosphates (dNTPs). dCTPase is highly expressed in multiple carcinomas and is associated with cancer cell sternness. Here we report on the development of the first potent and selective dCTPase inhibitors that enhance the cytotoxic effect of cytidine analogues in leukemia cells. Boronate 30 displays a promising in vitro ADME profile, including plasma and mouse microsomal half-lives, aqueous solubility, cell permeability and CYP inhibition, deeming it a suitable compound for in vivo studies.

  DOI：

  10.1021/acs.jmedchem.5b01741