2-(2,5-dimethoxyphenyl)-1H-benzo[d]imidazole | 940696-89-9

• 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-(2,5-dimethoxyphenyl)-1H-benzo[d]imidazole
• 英文别名: 2-(2,5-dimethoxyphenyl)-1H-benzimidazole
• CAS: 940696-89-9
• 化学式: C₁₅H₁₄N₂O₂
• mdl: MFCD08815182
• 分子量: 254.288
• InChiKey: OSMYIIXPXBEXRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,5-dimethoxyphenyl)-1H-benzo[d]imidazole 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-(biphenyl-4-yloxy)-2-fluorophenyl)-2-(2-(2,5-dimethoxyphenyl)-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-溴-2',5'-二甲氧基苯乙酮 在 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 11.0h， 生成 2-(2,5-dimethoxyphenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Synthesis of 2-Arylbenzimidazole Analogues

  摘要：

  Substituted 2-arylbenzimidazoles (4) were easily synthesized in good yields starting from the condensation reaction of 1,2-diaminobenzenes (1) with beta-ketosulfones (5) in the presence of boiling HOAc.

  DOI：

  10.3987/com-14-12966

文献信息

• A modern and practical laccase-catalysed route suitable for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
  作者：Mudzuli Maphupha、Wanyama P. Juma、Charles B. de Koning、Dean Brady

  DOI：10.1039/c8ra07377e

  日期：——

  Green chemistry: laccase in acetonitrile and buffer in the presence of O₂ can synthesise benzimidazoles and benzothiazoles in good yields.

  绿色化学：在乙腈和缓冲液中，存在氧气的情况下，漆酶可以合成苯并咪唑和苯并噻唑，产率较高。
• 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。
• A Simple, Mild and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles in the Presence of H2O2/HCl under Microwave Irradiation
  作者：Hossein Naeimi、Nasrin Alishahi

  DOI：10.1002/jccs.201100591

  日期：2012.8

  A simple, fast and efficient method for the preparation of several 2‐substituted benzimidazole derivatives is reported. Compounds were synthesized through a rapid one‐pot synthesis via microwave irradiation, starting from aldehydes and o‐phenylenediamine, in the presence of H2O2/HCl system in acetonitrile. The significant features of this method are short reaction times, high yields, easy and quick

  报道了一种简单，快速，有效的方法，用于制备几种2-取代的苯并咪唑衍生物。在乙腈中存在H 2 O 2 / HCl系统的情况下，由醛和邻苯二胺开始，通过微波辐射通过快速一锅法合成化合物。该方法的显着特点是反应时间短，收率高，产物容易，快速分离。
• Conventional and Microwave-Assisted Synthesis of Benzimidazole Derivatives and Their<i>In Vitro</i>Inhibition of Human Cyclooxygenase
  作者：Daniela Secci、Adriana Bolasco、Melissa D'Ascenzio、Flavio della Sala、Matilde Yáñez、Simone Carradori

  DOI：10.1002/jhet.1058

  日期：2012.9

  A large series of 1,2‐diaryl‐benzimidazole and 2‐aryl‐1H‐benzimidazole derivatives were synthesized with slight differences using both microwave irradiation and conventional heating methods. Usually higher yields and time reactions reduction were obtained with the former method. All compounds were assayed for their in vitro ability to inhibit human cyclooxygenases, and most of them showed an encouraging

  使用微波辐照和常规加热方法合成了一系列1,2-二芳基-苯并咪唑和2-芳基-1 H-苯并咪唑衍生物，但略有差异。通常，使用前一种方法可获得更高的产率和时间反应的减少。分析了所有化合物在体外抑制人环氧化酶的能力，其中大多数在微摩尔范围内显示出令人鼓舞的抑制活性和同工型选择性。
• A Zn based metal organic framework as a heterogeneous catalyst for C–C bond formation reactions
  作者：Kanagaraj Madasamy、Shanmugasundaram Kumaraguru、Velayutham Sankar、Subramaniyan Mannathan、Murugavel Kathiresan

  DOI：10.1039/c8nj05953e

  日期：——

  assess the role of the ligand and metal salt in the Knoevenagel condensation reaction. It was found that the Zn-Bp-BTC MOF catalyzed the reaction efficiently in comparison to its analogue Zn-BTC MOF and precursor Zn(NO3)2·6H2O. Finally, catalytic recycling and stability studies showed that the catalyst is able to mediate the reaction for up to five consecutive cycles without undergoing any significant chemical

  在本文中，我们报告了Zn-Bp-BTC MOF（Bp – 4,4'-联吡啶； BTC – 1,3,5-苯三羧酸； MOF –金属有机骨架）的合成和应用，作为介导的非均相催化剂有机反应。最初，通过改变溶剂，温度和催化剂负载量，使用Zn-Bp-BTC作为非均相催化剂优化了Knoevenagel缩合反应的条件。尽管反应在室温下使用甲醇作为溶剂进行，但60°C在较短的时间内提供了最佳收率。在优化的反应条件下，由相应的羰基前体和丙二腈（活性亚甲基对应物）制备了多种α，β-不饱和二氰基化合物。还进行了系统研究，以评估配体和金属盐在Knoevenagel缩合反应中的作用。发现Zn-Bp-BTC MOF与其类似的Zn-BTC MOF和前体Zn（NO3） 2 ·6H 2 O.最后，催化循环和稳定性研究表明，该催化剂能够介导多达五个连续循环反应而不经历任何显著化学或形态变化。此外，测试了该催化剂在多组分反应（MCR）中的功效。以Zn-Bp-BTC