2-(4-氯苯基)-1H-苯并咪唑-5-羧酸 | 174422-14-1

• 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-(4-氯苯基)-1H-苯并咪唑-5-羧酸
• 英文名称: 2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylic acid
• 英文别名: 2-(4-chlorophenyl)benzimidazole-5-carboxylic acid；AC271251；2-(4-chlorophenyl)-1H-1,3-benzodiazole-5-carboxylic acid；2-(4-chlorophenyl)-3H-benzimidazole-5-carboxylic acid
• CAS: 174422-14-1
• 化学式: C₁₄H₉ClN₂O₂
• mdl: MFCD00220089
• 分子量: 272.691
• InChiKey: KFEDCUOAVSSAAS-UHFFFAOYSA-N

物化性质

• 熔点：
  165-168 °C
• 沸点：
  545.1±56.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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-氯苯基)-1H-苯并咪唑-5-羧酸 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-chlorophenyl)-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：

  4-氯苯甲醛 在 sodium metabisulfite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-(4-氯苯基)-1H-苯并咪唑-5-羧酸
  参考文献：
  名称：

  Novel Clarithromycin Analogs with C-4” 2-arylbenzimidazolyl Bishydrazide Side Chain: Synthesis and Antibacterial Evaluation

  摘要：

  一系列新型的克拉霉素4”-O-2-芳基苯并咪唑衍生物被合成并评估。这些4”-O-2-芳基苯并咪唑衍生物对红霉素敏感菌株显示出优异的活性，并且相较于参考药物，对红霉素耐药菌株的活性显著提高。特别是化合物7c，其在C-4”双酰肼侧链上带有末端的2-（2-甲氧基苯基）苯并咪唑基团，不仅对红霉素敏感的肺炎链球菌ATCC49619和金黄色葡萄球菌ATCC25923表现出最强的活性，效能分别是母体克拉霉素的4倍和4倍，而且对表达mef基因和erm基因的红霉素耐药肺炎链球菌的活性也是最高的，分别是克拉霉素或阿奇霉素的133倍和32倍。

  DOI：

  10.2174/157018011797655269

文献信息

• Novel Clarithromycin Analogs with C-4” 2-arylbenzimidazolyl Bishydrazide Side Chain: Synthesis and Antibacterial Evaluation
  作者：Yunkun Qi、Ruixin Ma、Xin Li、Yue Hu、Siti Ma、Chao Cong、Xiaodong Ma、Wenping Cui、Shutao Ma

  DOI：10.2174/157018011797655269

  日期：2011.12.1

  A series of novel 4” -O-2-arylbenzimidazolyl derivatives of clarithromycin were synthesized and evaluated. These 4” -O-2-arylbenzimidazolyl derivatives demonstrated excellent activity against erythromycin-susceptible strains and showed remarkably improved activity against erythromycin-resistant strains compared with the references. In particular, compound 7c, which possesses the terminal 2-(2-methoxyphenyl)benzimidazolyl group on the C-4” bishydrazide side chain, not only presented the most potent activity against erythromycin-susceptible Streptococcus pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923, exhibiting 4-fold and 4-fold higher efficacy than the parent clarithromycin, but also displayed the highest activity against erythromycin-resistant Streptococcus pneumoniae expressing the mef gene and the erm gene, which was 133-fold and 32-fold better than clarithromycin or azithromycin, respectively.

  一系列新型的克拉霉素4”-O-2-芳基苯并咪唑衍生物被合成并评估。这些4”-O-2-芳基苯并咪唑衍生物对红霉素敏感菌株显示出优异的活性，并且相较于参考药物，对红霉素耐药菌株的活性显著提高。特别是化合物7c，其在C-4”双酰肼侧链上带有末端的2-（2-甲氧基苯基）苯并咪唑基团，不仅对红霉素敏感的肺炎链球菌ATCC49619和金黄色葡萄球菌ATCC25923表现出最强的活性，效能分别是母体克拉霉素的4倍和4倍，而且对表达mef基因和erm基因的红霉素耐药肺炎链球菌的活性也是最高的，分别是克拉霉素或阿奇霉素的133倍和32倍。
• Synthesis and antimicrobial activity of some new benzimidazole carboxylates and carboxamides
  作者：Gülgün Ayhan-Kılcıgil、Meral Tunçbilek、Nurten Altanlar、Hakan Göker

  DOI：10.1016/s0014-827x(99)00059-2

  日期：1999.8

  Some benzimidazole carboxylates and carboxamides were synthesized and evaluated for their antimicrobial activities against Staphylococcus aureus, Escherichia coli and Candida albicans. Among the investigated compounds 2d exhibited best activity against C. albicans.

  合成了一些苯并咪唑羧酸盐和羧酰胺，并评估了它们对金黄色葡萄球菌，大肠杆菌和白色念珠菌的抗菌活性。在所研究的化合物中，2d表现出对白色念珠菌的最佳活性。
• Aqueous 1 M Glucose Solution as a Novel and Fully Green Reaction Medium and Catalyst for the Oxidant-Free Synthesis of 2-Arylbenzimidazoles
  作者：Shahnaz Rostamizadeh、Reza Aryan、Hamid Reza Ghaieni

  DOI：10.1080/00397911.2010.492460

  日期：2011.5.4

  glucose solution as reaction medium and catalyst under one-pot oxidant-free conditions. The desired products were obtained at 60 °C with good to excellent yields, and the reaction was performed chemoselectively without formation of 1,2-disubstituted benzimidazoles. No need for any extra oxidant, simple workup, and use of carbohydrates as fully green promoters are some advantages of the present work

  摘要 以1 M葡萄糖溶液为反应介质和催化剂，在一锅无氧化剂条件下，进行了各种邻苯二胺与取代苯甲醛的反应。所需产物在 60 °C 下以良好到极好的收率获得，并且该反应通过化学选择性进行，没有形成 1,2-二取代苯并咪唑。不需要任何额外的氧化剂、简单的后处理以及使用碳水化合物作为完全绿色的促进剂是目前工作的一些优点。
• 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）。