4-((2-(2-(5-isopropyl-2-methylphenylamino)-2-oxoethyl)-1H-benzo[d]imidazol-1-yl)methyl)benzoic acid | 1602748-93-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-((2-(2-(5-isopropyl-2-methylphenylamino)-2-oxoethyl)-1H-benzo[d]imidazol-1-yl)methyl)benzoic acid
• 英文别名: 4-[[2-[2-(2-methyl-5-propan-2-ylanilino)-2-oxoethyl]benzimidazol-1-yl]methyl]benzoic acid
• CAS: 1602748-93-5
• 化学式: C₂₇H₂₇N₃O₃
• 分子量: 441.53
• InChiKey: INZMMFYFMNOKOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((2-(2-(5-isopropyl-2-methylphenylamino)-2-oxoethyl)-1H-benzo[d]imidazol-1-yl)methyl)benzoic acid 、 N,N-二甲基-1,3-二氨基丙烷 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到N-((3-dimethylamino)propyl)-4-((2-(2-(5-isopropyl-2-methylphenylamino)-2-oxoethyl)-1H-benzo[d]imidazol-1-yl)methyl)benzamide
  参考文献：
  名称：

  Discovery of benzimidazole derivatives as modulators of mitochondrial function: A potential treatment for Alzheimer's disease

  摘要：

  In this study, we designed a library of compounds based on the structures of well-known ligands of the 18 kDa translocator protein (TSPO), one of the putative components of the mPTP. We performed diverse mitochondrial functional assays to assess their ability to restore cells from A beta-induced toxicity in vitro and in vivo. Among tested compounds, compound 25 effectively improved cognitive function in animal models of AD. Given the excellent in vitro and in vivo activity and a favorable pharmacokinetic profile of compound 25, we believe that it can serve as a promising lead compound for a potential treatment option for AD. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.11.017
• 作为产物：
  描述：

  (1H-苯并咪唑-2-基)-乙酸 在 三乙胺 、 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 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 4-((2-(2-(5-isopropyl-2-methylphenylamino)-2-oxoethyl)-1H-benzo[d]imidazol-1-yl)methyl)benzoic acid
  参考文献：
  名称：

  Discovery of benzimidazole derivatives as modulators of mitochondrial function: A potential treatment for Alzheimer's disease

  摘要：

  In this study, we designed a library of compounds based on the structures of well-known ligands of the 18 kDa translocator protein (TSPO), one of the putative components of the mPTP. We performed diverse mitochondrial functional assays to assess their ability to restore cells from A beta-induced toxicity in vitro and in vivo. Among tested compounds, compound 25 effectively improved cognitive function in animal models of AD. Given the excellent in vitro and in vivo activity and a favorable pharmacokinetic profile of compound 25, we believe that it can serve as a promising lead compound for a potential treatment option for AD. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.11.017

文献信息

• BENZIMIDAZOLE DERIVATIVES AS MITOCHONDRIAL FUNCTION MODULATORS
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20140114067A1

  公开（公告）日：2014-04-24

  Provided are a benzimidazole derivative modulating mitochondrial functions and having pharmaceutical activity as a neuro-protective agent, and a pharmaceutical composition including the compound as an active ingredient.

  提供了一种调节线粒体功能并具有药用活性作为神经保护剂的苯并咪唑衍生物，以及包含该化合物作为活性成分的药物组合物。
• Discovery of benzimidazole derivatives as modulators of mitochondrial function: A potential treatment for Alzheimer's disease
  作者：TaeHun Kim、Ha Yun Yang、Beoung Gun Park、Seo Yun Jung、Jong-Hyun Park、Ki Duk Park、Sun-Joon Min、Jinsung Tae、Hyejin Yang、Suengmok Cho、Sung Jin Cho、Hyundong Song、Inhee Mook-Jung、Jiyoun Lee、Ae Nim Pae

  DOI：10.1016/j.ejmech.2016.11.017

  日期：2017.1

  In this study, we designed a library of compounds based on the structures of well-known ligands of the 18 kDa translocator protein (TSPO), one of the putative components of the mPTP. We performed diverse mitochondrial functional assays to assess their ability to restore cells from A beta-induced toxicity in vitro and in vivo. Among tested compounds, compound 25 effectively improved cognitive function in animal models of AD. Given the excellent in vitro and in vivo activity and a favorable pharmacokinetic profile of compound 25, we believe that it can serve as a promising lead compound for a potential treatment option for AD. (C) 2016 Elsevier Masson SAS. All rights reserved.