6-ethoxycarbonyl-2-isopropylbenzoimidazole

• 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: 6-ethoxycarbonyl-2-isopropylbenzoimidazole
• 英文别名: ethyl 2-(propan-2-yl)-1H-1,3-benzodiazole-6-carboxylate；ethyl 2-propan-2-yl-3H-benzimidazole-5-carboxylate
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: UGAOCEXELRVNGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-ethoxycarbonyl-2-isopropylbenzoimidazole 在 甲醇 、 一水合肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4''-O-(2-isopropyl-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：

  3,4-二氨基苯甲酸 在 盐酸 、 甲酸 、 硫酸 作用下， 以 水 为溶剂， 生成 6-ethoxycarbonyl-2-isopropylbenzoimidazole
  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

文献信息

• Improved and ligand-free copper-catalyzed cyclization for an efficient synthesis of benzimidazoles from <i>o</i>-bromoarylamine and nitriles
  作者：Emmanuel Mintah Bonku、Hongjian Qin、Abdullajon Odilov、Safomuddin Abduahadi、Samuel Desta Guma、Feipu Yang、Fuqiang Zhu、Haji A. Aisa、Jingshan Shen

  DOI：10.1039/d4ra00245h

  日期：——

  improved copper-catalyzed cyclization for an efficient synthesis of benzimidazoles from o-bromoarylamine and nitriles, under mild and ligand-free conditions. The optimal conditions yielded exceptional products of up to 98%, demonstrating the broad applicability of this synthetic strategy in generating a wide range of valuable imidazole derivatives. This methodology enables the efficient synthesis of various

  我们提出了一种改进的铜催化环化，用于在温和且无配体的条件下从邻溴芳胺和腈有效合成苯并咪唑。最佳条件产生了高达 98% 的优质产物，证明了该合成策略在生成各种有价值的咪唑衍生物方面具有广泛的适用性。该方法能够有效合成各种取代的苯并咪唑衍生物，并为传统方法提供了一种环境友好的替代方案。通过消除与传统合成方法相关的刺激性试剂和高温的使用，该方法被证明更加有效和稳健。值得注意的是，我们成功地将这种合成方法应用于苯达唑和噻苯达唑的合成，在 100 克规模上，产率分别为 82% 和 78%。
• Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives
  作者：Chao Cong、Haiyang Wang、Yue Hu、Chen Liu、Siti Ma、Xin Li、Jichao Cao、Shutao Ma

  DOI：10.1016/j.ejmech.2011.04.004

  日期：2011.7

  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.