5,6-difluoro-1-hydroxy-1H-benzo[d]imidazol-2(3H)-one | 1400979-61-4

• 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: 5,6-difluoro-1-hydroxy-1H-benzo[d]imidazol-2(3H)-one
• 英文别名: 5,6-difluoro-3-hydroxy-1H-benzimidazol-2-one
• CAS: 1400979-61-4
• 化学式: C₇H₄F₂N₂O₂
• 分子量: 186.118
• InChiKey: INIVKKDTSCXPTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二氟苯异氰酸酯 在 palladium 10% on activated carbon 、 氢气 、 lead(IV) tetraacetate 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 反应 0.58h， 生成 5,6-difluoro-1-hydroxy-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  Synthesis and SAR of 1-Hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of d-Amino Acid Oxidase

  摘要：

  A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of D-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents on the benzene ring with IC50 values of the compounds ranging from 70 nM to greater than 100 mu M. Structure-activity relationships of this new class of DAAO inhibitors will be presented in detail along with comparisons to previously published SAR data from other classes of DAAO inhibitors. Two of these compounds were given to mice orally together with D-serine to assess their effects on plasma D-serine pharmacokinetics.

  DOI：

  10.1021/ml300212a

文献信息

• Synthesis and SAR of 1-Hydroxy-1<i>H</i>-benzo[<i>d</i>]imidazol-2(3<i>H</i>)-ones as Inhibitors of <scp>d</scp>-Amino Acid Oxidase
  作者：James F. Berry、Dana V. Ferraris、Bridget Duvall、Niyada Hin、Rana Rais、Jesse Alt、Ajit G. Thomas、Camilo Rojas、Kenji Hashimoto、Barbara S. Slusher、Takashi Tsukamoto

  DOI：10.1021/ml300212a

  日期：2012.10.11

  A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of D-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents on the benzene ring with IC50 values of the compounds ranging from 70 nM to greater than 100 mu M. Structure-activity relationships of this new class of DAAO inhibitors will be presented in detail along with comparisons to previously published SAR data from other classes of DAAO inhibitors. Two of these compounds were given to mice orally together with D-serine to assess their effects on plasma D-serine pharmacokinetics.