2-(4-bromophenyl)benzimidazole-5-carboxylic acid | 1018300-89-4

• 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-(4-bromophenyl)benzimidazole-5-carboxylic acid
• 英文别名: 2-(4-bromophenyl)-3H-benzo[d]imidazole-5-carboxylic acid；2-(4-bromophenyl)-3H-benzimidazole-5-carboxylic acid
• CAS: 1018300-89-4
• 化学式: C₁₄H₉BrN₂O₂
• mdl: MFCD10007794
• 分子量: 317.142
• InChiKey: AOXAYONETOKCQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)benzimidazole-5-carboxylic acid 在 甲醇 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 4''-O-(2-(4-bromophenyl)-1H-benzimidazole-5-carbonyl)hydrazinecarbonylclarithromycin
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives

  摘要：

  Novel 4 ''-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4 '' bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the me! gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4 ''-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4 ''-O-(2-alkyl) benzimidazolyl derivatives. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.004
• 作为产物：
  描述：

  对溴苯甲醛 在 sodium metabisulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-bromophenyl)benzimidazole-5-carboxylic acid
  参考文献：
  名称：

  作为选择性丁酰胆碱酯酶抑制剂的新型甲酰胺和甲酰肼苯并咪唑的合成

  摘要：

  假设选择性抑制丁酰胆碱酯酶 (BChE) 有助于治疗阿尔茨海默病 (AD)。几项研究确定了 BChE 活性增加与 AD 发病之间的相关性。BChE 优于乙酰胆碱酯酶抑制的一个优势是 BChE 活性的缺失不会导致明显的生理障碍。然而，目前没有 BChE 抑制剂可作为 AD 的潜在治疗剂在商业上获得。在我们不断努力寻找有效的阿尔茨海默病 BChE 抑制剂的过程中，本研究共合成了 22 种具有多种取代的新型苯并咪唑，并评估了它们的抗胆碱酯酶活性。在合成的化合物中，2j和3f被发现表现出有效和选择性的 BChE 抑制作用，IC 50值分别为 1.13 和 1.46 μM。进行分子对接研究以合理化观察到的抑制活性。预计这些化合物具有高穿透血脑屏障的能力。此外，还进行了细胞增殖研究以评估感兴趣化合物的毒性特征。 图形概要 发现化合物3f是一种有效的选择性丁酰胆碱酯酶抑制剂，IC 50值为 1.46 µM。

  DOI：

  10.1007/s11030-022-10476-8

文献信息

• N-substituted benzimidazolyl c-Kit inhibitors and combinatorial benzimidazole library
  申请人：Crew Philip Andrew

  公开号：US20060116402A1

  公开（公告）日：2006-06-01

  Compounds represented by Formula (I): or a pharmaceutically acceptable salt or N-oxide thereof, are useful in the treatment of tumors. Combinatorial libraries composed of compounds represented by Formula (I) or benzimidazole compounds represented by Formula (II): are useful in providing compounds to assay for such therapeutically useful compounds.

  式(I)表示的化合物：或其药学上可接受的盐或N-氧化物，在肿瘤治疗中具有用途。由式(I)表示的化合物或式(II)表示的苯并咪唑化合物组成的组合库：在提供用于筛选此类治疗上有用的化合物的化合物方面具有用途。
• Fast and efficient method for the synthesis of 2-arylbenzimidazoles using MCM-41-SO₃H
  作者：Gholam Hossein Mahdavinia、Shahnaz Rostamizadeh、Ali Mohammad Amani、Hamid Sepehrian

  DOI：10.1515/hc-2011-0056

  日期：2012.2.1

  Nanosized MCM-41-SO₃H material based on ordered mesoporous silica gel with covalently attached sulfonic acid groups was synthesized and used as acid catalyst for green synthesis of 2-substituted benzimidazole derivatives. Echo-friendly protocol, short reaction times, easy and quick isolation of the products, and excellent yields are the main advantages of this procedure.

  基于有序介孔二氧化硅凝胶的纳米级MCM-41-SO₃H材料，具有共价连接的磺酸基团，被合成并用作2-取代苯并咪唑衍生物的绿色合成酸催化剂。这种方法的主要优点是环保协议、反应时间短、产品易于快速分离和产率优异。

• Solvent-free chemoselective synthesis of some novel substituted 2-arylbenzimidazoles using amino acid-based prolinium nitrate ionic liquid as catalyst
  作者：Shahnaz Rostamizadeh、Reza Aryan、Hamid Reza Ghaieni、Ali Mohammad Amani

  DOI：10.1002/jhet.35

  日期：2009.1

  A simple and eco-friendly protocol for the synthesis of substituted 2-arylbenzimidazoles is described. In this process, 2-arylbenzimidazoles were prepared in the presence of a newly introduced ionic liquid prolinium nitrate [Pro]NO3 as catalyst, under solvent-free condition. This process was performed under mild condition without using any oxidant with good to excellent yields and remarkable chemoselectivity

  描述了用于合成取代的2-芳基苯并咪唑的简单且生态友好的方案。在该方法中，在无溶剂条件下，在新引入的离子液体硝酸pro [Pro] NO 3作为催化剂的存在下，制备了2-芳基苯并咪唑。该过程在温和条件下进行，不使用任何氧化剂，在没有任何副产物的情况下，具有良好至优异的收率和出色的化学选择性。离子液体可以轻松回收再利用。杂环化学杂志，46，74（2009）。
• Very fast and efficient synthesis of some novel substituted 2-arylbenzimidazoles in water using ZrOCl2·nH2O on montmorillonite K10 as catalyst
  作者：Shahnaz Rostamizadeh、Ali Mohammad Amani、Reza Aryan、Hamid Reza Ghaieni、Leila Norouzi

  DOI：10.1007/s00706-008-0087-1

  日期：2009.5

  A simple and eco-friendly protocol for the synthesis of some novel substituted 2-arylbenzimidazoles was developed. In this process, these compounds were prepared in water as the solvent using ZrOCl2 center dot nH(2)O supported on montmorillonite K10 as an efficient water tolerating Lewis acid. The reaction was performed under mild conditions with good to excellent yields and remarkable chemoselectivity in the absence of any byproduct.
• N-SUBSTITUTED BENZIMIDAZOLYL C-KIT INHIBITORS AND COMBINATORIAL BENZIMIDAZOLE LIBRARY
  申请人：OSI Pharmaceuticals, Inc.

  公开号：EP1831206A2

  公开（公告）日：2007-09-12