1,3-bis(4-cyanobenzyl)-4,5-bisphenyl-imidazolium bromide | 1399982-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1,3-bis(4-cyanobenzyl)-4,5-bisphenyl-imidazolium bromide
• CAS: 1399982-82-1
• 化学式: Br*C₃₁H₂₃N₄
• 分子量: 531.454
• InChiKey: OLBQPLVOKIYEGR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  56.39
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,3-bis(4-cyanobenzyl)-4,5-bisphenyl-imidazolium bromide 、 silver(I) acetate 以 二氯甲烷 为溶剂， 反应 48.0h， 以81.3%的产率得到(1,3-bis(4-cyanobenzyl)-4,5-bisphenylimidazole-2-ylidene)silver(I) acetate
  参考文献：
  名称：

  Novel symmetrically p-benzyl-substituted 4,5-diaryl-imidazole N-heterocyclic carbene-silver(I) acetate complexes – Synthesis and biological evaluation

  摘要：

  Symmetrically substituted N-heterocyclic carbene (NHC) precursors 1a-e and 3a-e were synthesised by reacting 4,5-bisaryl-1H-imidazole with 2 equivalents of 4-benzyl bromide, 4-methylbenzyl bromide, 4-methoxybenzyl chloride, 4-methoxycarbonylbenzyl bromide or 4-cyanobenzyl bromide to give the 1,3-bis(p-benzyl substituted)-4,5-bisaryl-imidazolium halides. The NHC-silver(I) acetate complexes (1,3-bisbenzyl-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2a), (1,3-bis(4-methylbenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2b), (1,3-bis(4-methoxybenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2c), (1,3-bis(4-methoxycarbonylbenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2d), (1,3-bis(4-cyanobenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2e), (1,3-bisbenzyl-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4a), (1,3-bis(4-methylbenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4b), (1,3-bis(4-methoxybenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4c), (1,3-bis(4-methoxycarbonylbenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4d) and (1,3-bis(4-cyanobenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4e) were yielded by reacting these NHC precursors with silver(I) acetate. The silver(I) acetate complexes 2d, 2e and 4c were characterised by single crystal X-ray diffraction. Qualitative antibacterial studies against the Gram-negative bacteria Escherichia coli and the Gram-positive bacteria Staphylococcus aureus, using the Kirby-Bauer disc diffusion method were carried out on the ten NHC-silver(I) acetate complexes 2a-e and 4a-e. Also the IC50 values of these ten complexes were determined by an MTT-based assay against the human renal cancer cell line Caki-1 and the human breast cancer cell line MCF-7. The complexes 2a-e and 4a-e revealed the following IC50 values in mu M against Caki-1: 14 (+/- 1), 3.6 (+/- 1.0), 4.2 (+/- 0.5), 33 (+/- 2), 59 (+/- 4), 21 (+/- 1), 21 (+/- 2), 21 (+/- 1), 34 (+/- 2), 46 (+/- 2) and against MCF-7: 5.8 (+/- 0.6), 3.5 (+/- 0.4), 5.4 (+/- 0.3), 28 (+/- 1), 25 (+/- 2), 11 (+/- 2), 5.0 (+/- 0.3), 6.5 (+/- 0.4), 17 (+/- 1), 13 (+/- 1); respectively. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.07.006
• 作为产物：
  描述：

  4,5-二苯基咪唑 、 对氰基溴化苄 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以81%的产率得到1,3-bis(4-cyanobenzyl)-4,5-bisphenyl-imidazolium bromide
  参考文献：
  名称：

  Novel symmetrically p-benzyl-substituted 4,5-diaryl-imidazole N-heterocyclic carbene-silver(I) acetate complexes – Synthesis and biological evaluation

  摘要：

  Symmetrically substituted N-heterocyclic carbene (NHC) precursors 1a-e and 3a-e were synthesised by reacting 4,5-bisaryl-1H-imidazole with 2 equivalents of 4-benzyl bromide, 4-methylbenzyl bromide, 4-methoxybenzyl chloride, 4-methoxycarbonylbenzyl bromide or 4-cyanobenzyl bromide to give the 1,3-bis(p-benzyl substituted)-4,5-bisaryl-imidazolium halides. The NHC-silver(I) acetate complexes (1,3-bisbenzyl-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2a), (1,3-bis(4-methylbenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2b), (1,3-bis(4-methoxybenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2c), (1,3-bis(4-methoxycarbonylbenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2d), (1,3-bis(4-cyanobenzyl)-4,5-bisphenyl-imidazole-2-ylidene) silver(I) acetate (2e), (1,3-bisbenzyl-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4a), (1,3-bis(4-methylbenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4b), (1,3-bis(4-methoxybenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4c), (1,3-bis(4-methoxycarbonylbenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4d) and (1,3-bis(4-cyanobenzyl)-4,5-bis(4-methoxyphenyl)-imidazole-2-ylidene) silver(I) acetate (4e) were yielded by reacting these NHC precursors with silver(I) acetate. The silver(I) acetate complexes 2d, 2e and 4c were characterised by single crystal X-ray diffraction. Qualitative antibacterial studies against the Gram-negative bacteria Escherichia coli and the Gram-positive bacteria Staphylococcus aureus, using the Kirby-Bauer disc diffusion method were carried out on the ten NHC-silver(I) acetate complexes 2a-e and 4a-e. Also the IC50 values of these ten complexes were determined by an MTT-based assay against the human renal cancer cell line Caki-1 and the human breast cancer cell line MCF-7. The complexes 2a-e and 4a-e revealed the following IC50 values in mu M against Caki-1: 14 (+/- 1), 3.6 (+/- 1.0), 4.2 (+/- 0.5), 33 (+/- 2), 59 (+/- 4), 21 (+/- 1), 21 (+/- 2), 21 (+/- 1), 34 (+/- 2), 46 (+/- 2) and against MCF-7: 5.8 (+/- 0.6), 3.5 (+/- 0.4), 5.4 (+/- 0.3), 28 (+/- 1), 25 (+/- 2), 11 (+/- 2), 5.0 (+/- 0.3), 6.5 (+/- 0.4), 17 (+/- 1), 13 (+/- 1); respectively. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.07.006