methyl 2-(2-benzyl-1H-benzo[d]imidazol-1-yl)acetate | 667408-26-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(2-benzyl-1H-benzo[d]imidazol-1-yl)acetate
• 英文别名: (2-Benzyl-benzoimidazol-1-yl)-acetic acid methyl ester；methyl 2-(2-benzylbenzimidazol-1-yl)acetate
• CAS: 667408-26-6
• 化学式: C₁₇H₁₆N₂O₂
• mdl: MFCD02859131
• 分子量: 280.326
• InChiKey: LBONCJULYLIUAL-UHFFFAOYSA-N

物化性质

• 沸点：
  475.9±38.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)
• 溶解度：
  >42 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-benzyl-1H-benzo[d]imidazol-1-yl)acetate 在 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 2-(2-benzyl-1H-benzo[d]imidazol-1-yl)-N-(3,5-di-tert-butylphenyl)acetamide
  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：

  2-碘苯胺 在 ammonium hydroxide 、 copper(l) iodide 、 sodium hydride 、 L-脯氨酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 methyl 2-(2-benzyl-1H-benzo[d]imidazol-1-yl)acetate
  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.