1-[2-(4-chlorophenoxy)ethyl]-1H-benzimidazole

• 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: 1-[2-(4-chlorophenoxy)ethyl]-1H-benzimidazole
• 英文别名: 1-[2-(4-chlorophenoxy)ethyl]benzimidazole
• 化学式: C₁₅H₁₃ClN₂O
• mdl: MFCD01029222
• 分子量: 272.734
• InChiKey: WYJHITBILJDWSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯酚钾 在 四丁基溴化铵 、 四丁基碘化铵 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 34.0h， 生成 1-[2-(4-chlorophenoxy)ethyl]-1H-benzimidazole
  参考文献：
  名称：

  Design, synthesis, antibacterial and QSAR studies of benzimidazole and imidazole chloroaryloxyalkyl derivatives

  摘要：

  In view of obtaining some potential antibacterial compounds, we have described synthesis of some chloroaryloxyalkyl imidazole and benzimidazole derivatives. The relevant step in the synthetic sequence was the initial condensation of 4-chloro or 2,4-dichlorophenol with 1, n-dibromoalkanes (n = 2, 4, 5) to provide compounds 3a-f in sufficient yields. The subsequent condensation of 3a-f with some imidazole derivatives and benzimidazole afforded products 4a-1 and 5a-e in good yields. Some of compounds 4a-1 as well as 5a-e were tested in vitro against Salmonella typhi O-901 and Staphylococcus aureus A 15091. Compounds 4a and 4c showed considerable bactericidal activities against tested bacteria. Compound 4b showed significant activity against S. aureus A 15091 but was inactive against S. typhi O-901. Other compounds showed intermediate activities against S. aureus A 15091 but most of them were inactive against S. typhi O-901. Serniempirical AM1 calculations showed that negative electrostatic potentials around oxygen of the phenoxy and nitrogen of the imidazole moieties have direct effect on the antibacterial activity towards S. aureus A 15091. In QSAR analysis, different electronic, topologic, functional groups and physicochemical descriptors were calculated for each molecule and a three parametric equation was found between the log MIC and HOMO energy, hydration energy and number of primary carbon atoms of the molecules. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.014

文献信息

• Prodrug antibiotic screens
  申请人：Lewis Kim

  公开号：US20080027044A1

  公开（公告）日：2008-01-31

  Methods for identifying prodrug activity utilizing screens with microbial mutants, including null and conditional mutants, transiently gene-repressed microbes, and gene-overexpressing microbes, as well as pooled collections of these are provided. Effective prodrug antibiotics differentially kill or inhibit microbes overexpressing prodrug activating genes and allow non-expressing strains to grow and be readily identified. Methods for detecting prodrug antibiotic activity by detecting a lack of differential sensitivity of multidrug efflux mutant or deficient strains are also provided. Novel pharmaceutical compounds identified by the methods of the invention, pharmaceutical formulations, and methods for treating an infection comprising administering to a subject in need thereof an effective amount of a Compound of the Invention are also provided.