2-(4-chlorophenyl)-1-(4-methylbenzyl)-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: 2-(4-chlorophenyl)-1-(4-methylbenzyl)-1H-benzimidazole
• 英文别名: 2-(4-chlorophenyl)-1-(4-methylbenzyl)-1H-benzo[d]imidazole；2-(4-Chlorophenyl)-1-[(4-methylphenyl)methyl]benzimidazole
• 化学式: C₂₁H₁₇ClN₂
• 分子量: 332.832
• InChiKey: GYXLCULQFYEFBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-1-(4-methylbenzyl)-1H-benzimidazole 、 zinc(II) chloride 以 乙醇 为溶剂， 反应 5.0h， 以87%的产率得到dichlorobis(1-(4-methylbenzyl)-2-(4-chlorophenyl)-1H-benzimidazole-κN³)zinc(II)
  参考文献：
  名称：

  Synthesis and evaluation of anticancer properties of novel benzimidazole ligand and their cobalt(II) and zinc(II) complexes against cancer cell lines A-2780 and DU-145

  摘要：

  Eighteen new cobalt(II) or zinc(II) complexes of benzimidazole bearing 1-benzyl and 2-phenyl moieties were synthesized from the reaction of appropriate benzimidazole ligands and CoCl2 or ZnCl2. Their structural characterizations were done by IR, NMR (H-1, C-13) and UV-VIS spectrometers. Cytotoxic activities of eighteen new complexes and three benzimidazole ligands were determined using A-2780 (human ovarian) and DU-145 (human prostate) cell lines. Antitumor properties of all compounds were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Cell viability assay for the tested benzimidazole derivatives was performed and the LogIC(50) values of the compounds were calculated after a 24-hour treatment. All tested benzimidazole derivatives showed higher or comparable antitumor activity against A-2780 cell lines compared to the standard drug docetaxel with a LogIC(50) value of -0.81 mu M (p < 0.05). Eight of the examined compounds (1, 3, 5, 6, 7, 9, 10 and 13) showed high cytotoxic activity against A-2780 compared to the standard drug docetaxel. While the LogIC(50) of the docetaxel was -0.81 mu M for A-2780 cells at 24 h, the IC50 values of compounds 1, 3, 5, 6, 7, 9, 10 and 13 were - 0.97, -1.30, - 0.22, 0.13, - 0.16, - 0.73 and - 0.53 mu M, respectively. Three of the compounds 1, 18 and V showed high cytotoxic activity against DU-145 compared to docetaxel (p < 0.05). While the LogIC(50) of the docetaxel was -1.13 mu M for DU-145 cells at 24 h, the LogIC(50) values of compounds 1, 18 and V were 0.84, -0.38 and -0.66 mu M, respectively.

  DOI：

  10.1016/j.ica.2019.118977
• 作为产物：
  描述：

  N¹-(4-chlorobenzyl)-N¹-(4-methylbenzyl)benzene-1,2-diamine 在 tert-butylammonium hexafluorophosphate(V) 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 3.0h， 以37%的产率得到2-(4-chlorophenyl)-1-(4-methylbenzyl)-1H-benzimidazole
  参考文献：
  名称：

  分子内C(sp3)–H胺化电化学合成苯并[d]咪唑

  摘要：

  开发了用于合成苯并咪唑的电化学脱氢胺化反应。这种电合成方法可以解决 C(sp3)-H 分子内胺化合成反应的局限性，并为在没有过渡金属和氧化剂的情况下获得 1,2-二取代苯并咪唑提供新途径。在未分割的电解条件下，可以合成各种苯并咪唑衍生物，表现出官能团耐受性。

  DOI：

  10.1021/acs.joc.1c01842

文献信息

• Development of benzimidazole-based derivatives as antimicrobial agents and their synergistic effect with colistin against gram-negative bacteria
  作者：Eman M.E. Dokla、Nader S. Abutaleb、Sandra N. Milik、Daoyi Li、Karim El-Baz、Menna-Allah W. Shalaby、Rawan Al-Karaki、Maha Nasr、Christian D. Klein、Khaled A.M. Abouzid、Mohamed N. Seleem

  DOI：10.1016/j.ejmech.2019.111850

  日期：2020.1

  Gram-negative bacteria pose a distinctive risk worldwide, especially with the evolution of major resistance to carbapenems, fluoroquinolones and colistin. Therefore, development of new antibacterial agents to target Gram-negative infections is of utmost importance. Using phenotypic screening, we synthesized and tested thirty-one benzimidazole derivatives against E. coli JW55031 (TolC mutant strain). Compound 6c showed potent activity with MlC value of 2 mu g/ml, however, it lacked activity against several Gram-negative microbes with intact efflux systems, including E. coli BW25113 (wild-type strain). Combination of 6c with colistin partially restored its antibacterial activity against wild strains (MlC range, 8-16 mu g/ml against E. coli, K. pneumoniae, A. baumannii, and P. aeruginosa). 6c exhibited no cytotoxicity against two mammalian cell lines. Therefore, compound 6c represents a promising lead for further optimization to overcome Gram-negative resistance alone or in combination therapy. (C) 2019 Elsevier Masson SAS. All rights reserved.