2-[4-(2-chlorophenoxy)phenyl]-N-(2-cyclopropylethyl)-3H-benzimidazole-5-carboxamide | 1123819-05-5

• 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: 2-[4-(2-chlorophenoxy)phenyl]-N-(2-cyclopropylethyl)-3H-benzimidazole-5-carboxamide
• CAS: 1123819-05-5
• 化学式: C₂₅H₂₂ClN₃O₂
• 分子量: 431.922
• InChiKey: HLTZCMCWHWUHJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二氨基苯甲酸 在 sodium metabisulfite 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-[4-(2-chlorophenoxy)phenyl]-N-(2-cyclopropylethyl)-3H-benzimidazole-5-carboxamide
  参考文献：
  名称：

  Benzimidazole-carboxamides as potent and bioavailable stearoyl-CoA desaturase (SCD1) inhibitors from ligand-based virtual screening and chemical optimization

  摘要：

  The discovery of potent benzimidazole stearoyl-CoA desaturase (SCD1) inhibitors by ligand-based virtual screening is described. ROCS 3D-searching gave a favorable chemical motif that was subsequently optimized to arrive at a chemical series of potent and promising SCD1 inhibitors. In particular, compound SAR224 was selected for further pharmacological profiling based on favorable in vitro data. After oral administration to male ZDF rats, this compound significantly decreased the serum fatty acid desaturation index, thus providing conclusive evidence for SCD1 inhibition in vivo by SAR224. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.030

文献信息

• Benzimidazole-carboxamides as potent and bioavailable stearoyl-CoA desaturase (SCD1) inhibitors from ligand-based virtual screening and chemical optimization
  作者：Hans Matter、Gerhard Zoller、Andreas W. Herling、Juan-Antonio Sanchez-Arias、Christophe Philippo、Claudie Namane、Markus Kohlmann、Anja Pfenninger、Marc D. Voss

  DOI：10.1016/j.bmcl.2013.01.030

  日期：2013.3

  The discovery of potent benzimidazole stearoyl-CoA desaturase (SCD1) inhibitors by ligand-based virtual screening is described. ROCS 3D-searching gave a favorable chemical motif that was subsequently optimized to arrive at a chemical series of potent and promising SCD1 inhibitors. In particular, compound SAR224 was selected for further pharmacological profiling based on favorable in vitro data. After oral administration to male ZDF rats, this compound significantly decreased the serum fatty acid desaturation index, thus providing conclusive evidence for SCD1 inhibition in vivo by SAR224. (C) 2013 Elsevier Ltd. All rights reserved.