1-[(4-chlorophenyl)methyl]-2-methyl-N-[(1R)-1-phenylpropyl]-1H-benzimidazole-5-carboxamide | 1168138-16-6

• 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: 1-[(4-chlorophenyl)methyl]-2-methyl-N-[(1R)-1-phenylpropyl]-1H-benzimidazole-5-carboxamide
• 英文别名: 1-[(4-chlorophenyl)methyl]-2-methyl-N-[(1R)-1-phenylpropyl]benzimidazole-5-carboxamide
• CAS: 1168138-16-6
• 化学式: C₂₅H₂₄ClN₃O
• 分子量: 417.938
• InChiKey: YBXPFAJXLHONMQ-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(4-氯苄基氨基)-3-氨基苯甲酸甲酯 在 溶剂黄146 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.5h， 生成 1-[(4-chlorophenyl)methyl]-2-methyl-N-[(1R)-1-phenylpropyl]-1H-benzimidazole-5-carboxamide
  参考文献：
  名称：

  Discovery of GSK1997132B a novel centrally penetrant benzimidazole PPARγ partial agonist

  摘要：

  The peroxisome proliferator-activated receptor gamma (PPAR gamma) is a ligand-activated nuclear receptor, thought to play a role in energy metabolism, glucose homeostasis and microglia-mediated neuroinflammation. A novel benzimidazole series of centrally penetrant PPAR gamma partial agonists has been identified. The optimization of PPAR gamma activity and in vivo pharmacokinetics leading to the identification of GSK1997132B a potent, metabolically stable and centrally penetrant PPAR gamma partial agonist, is described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.088

文献信息

• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009083526A1

  公开（公告）日：2009-07-09

  The invention relates to novel benzimidazole compounds of formula (I) wherein R1 to R1 are as defined in the specification, pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds that are agonists of peroxisome proliferators-activated receptorγ (PPARγ).

  这项发明涉及公式（I）中R1到R1所定义的新型苯并咪唑化合物，其药学上可接受的盐，含有它们的药物组合物以及它们在医学上的用途。具体而言，该发明涉及激动过氧化物酶体增殖物激活受体γ（PPARγ）的激动剂化合物。
• Discovery of GSK1997132B a novel centrally penetrant benzimidazole PPARγ partial agonist
  作者：Mairi Sime、Amanda C. Allan、Paul Chapman、Charlotte Fieldhouse、Gerard M.P. Giblin、Mark P. Healy、Millard H. Lambert、Lisa M. Leesnitzer、Ann Lewis、Raymond V. Merrihew、Richard A. Rutter、Rosemary Sasse、Barry G. Shearer、Timothy M. Wilson、Robert X. Xu、David J. Virley

  DOI：10.1016/j.bmcl.2011.06.088

  日期：2011.9

  The peroxisome proliferator-activated receptor gamma (PPAR gamma) is a ligand-activated nuclear receptor, thought to play a role in energy metabolism, glucose homeostasis and microglia-mediated neuroinflammation. A novel benzimidazole series of centrally penetrant PPAR gamma partial agonists has been identified. The optimization of PPAR gamma activity and in vivo pharmacokinetics leading to the identification of GSK1997132B a potent, metabolically stable and centrally penetrant PPAR gamma partial agonist, is described. (C) 2011 Elsevier Ltd. All rights reserved.