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.
• Electrochemical Synthesis of Benzo[<i>d</i>]imidazole via Intramolecular C(sp³)–H Amination
  作者：An Li、Caohui Li、Tao Yang、Zan Yang、Yu Liu、LiJun Li、KeWen Tang、Congshan Zhou

  DOI：10.1021/acs.joc.1c01842

  日期：2023.2.17

  An electrochemical dehydrogenative amination for the synthesis of benzimidazoles was developed. This electrosynthesis method could address the limitations of the C(sp3)–H intramolecular amination synthesis reaction and provide novel access to obtain 1,2-disubstituted benzimidazoles without transition metals and oxidants. Under undivided electrolytic conditions, various benzimidazole derivatives could

  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。
• 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
  作者：Ülkü Yılmaz、Suat Tekin、Nesrin Buğday、Kemal Yavuz、Hasan Küçükbay、Süleyman Sandal

  DOI：10.1016/j.ica.2019.118977

  日期：2019.9

  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.