6-chloro-2-[4-(trifluoromethyl)phenyl]-1H-benzimidazole | 911051-65-5

• 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: 6-chloro-2-[4-(trifluoromethyl)phenyl]-1H-benzimidazole
• CAS: 911051-65-5
• 化学式: C₁₄H₈ClF₃N₂
• 分子量: 296.679
• InChiKey: QZGYYAVVICPBNP-UHFFFAOYSA-N

物化性质

• 沸点：
  417.8±55.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-2-[4-(trifluoromethyl)phenyl]-1H-benzimidazole 、 2-氯-1-吗琳乙-1-酮 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以21%的产率得到2-[6-Chloro-2-[4-(trifluoromethyl)phenyl]benzimidazol-1-yl]-1-morpholin-4-ylethanone
  参考文献：
  名称：

  Synthesis, pharmacology and molecular modeling of N-substituted 2-phenyl-indoles and benzimidazoles as potent GABAA agonists

  摘要：

  Among the known non-benzodiazepine hypnotic drugs, Zolpidem (1 a), Indiplon (2a) and Zaleplon (2b) have shown high affinity and selectivity for the a, subunit of the GABA-A receptor. Our group has performed pharmacophoric and ADMET-prediction studies to evaluate a virtual library of new molecules based on privileged structures. Among these, we have synthesized a library of N-substituted indoles and a library of N-substituted benzimidazoles. Afterwards, in vitro screening and in vivo spontaneous motor activity in mice has revealed molecules with good in vitro affinities for the a, receptor and potent in vivo induction of sedation. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.031
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 4-氯-1,2-苯二胺 在 sodium metabisulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 6-chloro-2-[4-(trifluoromethyl)phenyl]-1H-benzimidazole
  参考文献：
  名称：

  Synthesis, pharmacology and molecular modeling of N-substituted 2-phenyl-indoles and benzimidazoles as potent GABAA agonists

  摘要：

  Among the known non-benzodiazepine hypnotic drugs, Zolpidem (1 a), Indiplon (2a) and Zaleplon (2b) have shown high affinity and selectivity for the a, subunit of the GABA-A receptor. Our group has performed pharmacophoric and ADMET-prediction studies to evaluate a virtual library of new molecules based on privileged structures. Among these, we have synthesized a library of N-substituted indoles and a library of N-substituted benzimidazoles. Afterwards, in vitro screening and in vivo spontaneous motor activity in mice has revealed molecules with good in vitro affinities for the a, receptor and potent in vivo induction of sedation. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.031

文献信息

• Synthesis, pharmacology and molecular modeling of N-substituted 2-phenyl-indoles and benzimidazoles as potent GABAA agonists
  作者：José Luis Falcó、Maria Piqué、Miguel González、Irma Buira、Eva Méndez、Jose Terencio、Cristina Pérez、Marta Príncep、Albert Palomer、Antonio Guglietta

  DOI：10.1016/j.ejmech.2006.03.031

  日期：2006.8

  Among the known non-benzodiazepine hypnotic drugs, Zolpidem (1 a), Indiplon (2a) and Zaleplon (2b) have shown high affinity and selectivity for the a, subunit of the GABA-A receptor. Our group has performed pharmacophoric and ADMET-prediction studies to evaluate a virtual library of new molecules based on privileged structures. Among these, we have synthesized a library of N-substituted indoles and a library of N-substituted benzimidazoles. Afterwards, in vitro screening and in vivo spontaneous motor activity in mice has revealed molecules with good in vitro affinities for the a, receptor and potent in vivo induction of sedation. (c) 2006 Elsevier SAS. All rights reserved.