2-(2,5-二氯苯基)-苯并咪唑 | 14225-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(2,5-二氯苯基)-苯并咪唑
• 中文别名: 2-(2,5-二氯苯基)-1H-苯并咪唑
• 英文名称: 2-(2,5-dichlorophenyl)-1H-benzo[d]imidazole
• 英文别名: 2-(2,5-Dichlorophenyl)-1H-benzimidazole
• CAS: 14225-80-0
• 化学式: C₁₃H₈Cl₂N₂
• mdl: MFCD06758818
• 分子量: 263.126
• InChiKey: XWESCMJAJHAFPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(2,5-二氯苯基)-苯并咪唑 在 sodium hydride 、 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 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.0h， 生成 N-(5-isopropyl-2-methylphenyl)-2-(2-(2,5-dichlorophenyl)-1H-benzo[d]imidazol-1-yl)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 、 L-脯氨酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 10.0h， 生成 2-(2,5-二氯苯基)-苯并咪唑
  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

• Visible-Light Photoredox Catalyzed Double C–H Functionalization: Radical Cascade Cyclization of Ethers with Benzimidazole-Based Cyanamides
  作者：Si Jiang、Xiao-Jing Tian、Shu-Yao Feng、Jiang-Sheng Li、Zhi-Wei Li、Cui-Hong Lu、Chao-Jun Li、Wei-Dong Liu

  DOI：10.1021/acs.orglett.0c03853

  日期：2021.2.5

  simple ethers with cyanamides is developed at room temperature. This strategy involves sequential inert Csp3-H/Csp2-H functionalizations through intermolecular addition reaction of oxyalkyl radicals to N-cyano groups followed by radical cyclization of iminyl radicals in situ generated with C-2 aryl rings. This method allows for efficient synthesis of tetracyclic benzo[4,5]imidazo[1,2-c]quinazolines. Importantly

  在室温下开发了一种简单的醚与氰胺的可见光光氧化还原催化的自由基级联环化反应。该策略涉及通过氧烷基自由基与N-氰基的分子间加成反应，随后通过C-2芳基环原位产生的亚氨基自由基的自由基环化，依次进行惰性C sp3- H / C sp2- H官能化。该方法可以有效合成四环苯并[4,5]咪唑并[1,2- c ]喹唑啉。重要的是，这是氰酰胺分子间-分子间自由基级联环化反应的第一个例子。
• 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。
• One-pot tandem approach for the synthesis of benzimidazoles and benzothiazoles from alcohols
  作者：Goravanahalli M. Raghavendra、Ajjahalli B. Ramesha、Cigalli N. Revanna、Kebbahalli N. Nandeesh、Kempegowda Mantelingu、Kanchugarakoppal S. Rangappa

  DOI：10.1016/j.tetlet.2011.08.037

  日期：2011.10

  Propylphosphonic anhydride (®T3P) has been demonstrated to be an efficient and mild reagent for the one-pot synthesis of benzimidazoles and benzothiazoles from variety of alcohols. Mild conditions, short reaction time, broad functional group tolerance, low epimerization, easy and quick isolation of the products, excellent chemo selectivity, and excellent yields are main advantages of this procedure

  已证明丙基膦酸酐（®T3P）是一种高效温和的试剂，用于由多种醇一锅合成苯并咪唑和苯并噻唑。温和的条件，短的反应时间，宽泛的官能团耐受性，低差向异构化，产物的简便快速分离，优异的化学选择性和优异的收率是该方法的主要优点。因此，本方法利用醇代替醛。
• Electrochemical synthesis of 5-trifluoroethyl dihydrobenzimidazo[2,1-a] isoquinolines from pendent unactivated alkenes via radical relay
  作者：Yi Lv、Jia-Ying Dai、Zi-Xin Zhao、Jia Liu、Zhi-Wei Li、Cui-Hong Lu、Yue-Fei Zhang、Wei-Dong Liu、Jiang-Sheng Li

  DOI：10.1016/j.tetlet.2023.154410

  日期：2023.4
• 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.