N-[3-[(3-bromophenyl)methyl]benzimidazol-5-yl]-2,2-dimethylpropanamide | 1246241-87-1

• 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-[3-[(3-bromophenyl)methyl]benzimidazol-5-yl]-2,2-dimethylpropanamide
• CAS: 1246241-87-1
• 化学式: C₁₉H₂₀BrN₃O
• 分子量: 386.291
• InChiKey: BXGIBQOYDZMTQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[3-[(3-bromophenyl)methyl]benzimidazol-5-yl]-2,2-dimethylpropanamide 、 4-氟-2-甲氧基苯硼酸 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.08h， 生成 N-[3-[[3-(4-fluoro-2-methoxyphenyl)phenyl]methyl]benzimidazol-5-yl]-2,2-dimethylpropanamide
  参考文献：
  名称：

  Identification and hit-to-lead optimization of a novel class of CB1 antagonists

  摘要：

  The discovery, synthesis and preliminary structure-activity relationships (SARs) of a novel class of CB1 antagonists is described. Initial optimization of benzimidazole-based screening hit 4 led to the identification of 'inverted' indole-based lead compound 18c with improved properties versus compound 4 including reduced A log P, improved microsomal stability and improved aqueous solubility. Compound 18c demonstrates in vivo CB1 antagonist efficacy (CB1 agonist induced hypothermia model) and is orally bioavailable in rat. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.091
• 作为产物：
  描述：

  、 原甲酸三乙酯 在 对甲苯磺酸 作用下， 生成 N-[3-[(3-bromophenyl)methyl]benzimidazol-5-yl]-2,2-dimethylpropanamide
  参考文献：
  名称：

  Identification and hit-to-lead optimization of a novel class of CB1 antagonists

  摘要：

  The discovery, synthesis and preliminary structure-activity relationships (SARs) of a novel class of CB1 antagonists is described. Initial optimization of benzimidazole-based screening hit 4 led to the identification of 'inverted' indole-based lead compound 18c with improved properties versus compound 4 including reduced A log P, improved microsomal stability and improved aqueous solubility. Compound 18c demonstrates in vivo CB1 antagonist efficacy (CB1 agonist induced hypothermia model) and is orally bioavailable in rat. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.091