2-(4-Chloro-phenyl)-1H-benzoimidazole-5-carbonyl chloride | 773795-91-8

• 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-Chloro-phenyl)-1H-benzoimidazole-5-carbonyl chloride
• CAS: 773795-91-8
• 化学式: C₁₄H₈Cl₂N₂O
• 分子量: 291.136
• InChiKey: YUGTXRKLSBOGPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.75
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2'-O-acetyl-4'-O-hydrazinecarbonylclarithromycin 、 2-(4-Chloro-phenyl)-1H-benzoimidazole-5-carbonyl chloride 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 生成
  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 、 sodium sulfide 、 氯化亚砜 、 copper diacetate 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 2-(4-Chloro-phenyl)-1H-benzoimidazole-5-carbonyl chloride
  参考文献：
  名称：

  Goeker, Hakan; Tebrizli, Emin; Abbasoglu, Ufuk, Il Farmaco, 1996, vol. 51, # 1, p. 53 - 58

  摘要：

  DOI：

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 of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity
  作者：Hakan Göker、Meral Tunçbilek、Gülgün Ayhan、Nurten Altanlar

  DOI：10.1016/s0014-827x(98)00045-7

  日期：1998.6

  A series of 1,2-disubstituted benzimidazole-5(6)-carboxamides was prepared and evaluated in vitro for antimicrobial activity against Staphyloccus aureus, Escherichia coli and Candida albicans. The precursor benzimidazolecarboxylic acids 4a-c and 9a-c were prepared via oxidative condensation of diaminobenzoic acids with aldehydes and via several steps over the 2(1H)-benzimidazolones, respectively. All acids were converted to their acyl chlorides with SOCI2, then amidified with several N,N'-dialkylaminoethyl derivatives. Compounds 8a-c, 20 and 22 exhibited the best activity. (C) 1998 Elsevier Science S.A. All rights reserved.