1,3-bis(4-methylbenzyl)-4,5-bis(4-methylphenyl)-1H-imidazol-3-ium bromide | 1428619-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-bis(4-methylbenzyl)-4,5-bis(4-methylphenyl)-1H-imidazol-3-ium bromide
• 英文别名: 1,3-di(p-methylbenzyl)-4,5-di(p-methylphenyl)imidazolium bromide
• CAS: 1428619-78-6
• 化学式: Br*C₃₃H₃₃N₂
• 分子量: 537.542
• InChiKey: TVOBUMODVPHBPW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 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：
  0.18
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,3-bis(4-methylbenzyl)-4,5-bis(4-methylphenyl)-1H-imidazol-3-ium bromide 在 三乙胺 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 11.5h， 生成 (1,3-di(p-methylbenzyl)-4,5-di(p-methylphenyl)imidazol-2-ylidene)gold(I)(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl-1-thiolate)
  参考文献：
  名称：

  新型钌（II）和金（I）NHC配合物：合成，表征和其抗癌性能评估

  摘要：

  报道了新型Ru（II）-和Au（I）-N-杂环卡宾的合成，表征和生物学评估。所述NHC-钌（II）络合物（1 - 6）通过用银适当取代的咪唑鎓溴化物反应而合成2 O，形成NHC-溴化银原位随后用二聚转移金属化p -cymene钌（II）二氯化物。以类似方式将NHC-氯化金（I）络合物（NHC-Au（I）Cl）7 – 9用二甲基硫代氯化金（I）作金属转移剂合成了这些化合物。在NHC-金的配体交换（I）氯化物，通过或者与乙酸银络合物反应以得到NHC -金（I）乙酸盐（NHC -金（I）OAC）达到10 - 12或反应的NHC-金（I）在碱性条件下用2'，3'，4'，6'-四-O-乙酰基-1-硫代-β- d-吡喃葡萄糖（SR）氯化物得到NHC-金（I）-（2 '，3'，4'，6'-四-O-乙酰基-β- d-吡喃葡萄糖基-1-硫醇盐）络合物（NHC-Au（I）SR）13 – 15。Ru（II）-N

  DOI：

  10.1021/om400819p
• 作为产物：
  描述：

  4,4'-二甲基联苯甲酰 在 sodium hydrogen sulfate 、 nitrosomethane 、 potassium carbonate 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 生成 1,3-bis(4-methylbenzyl)-4,5-bis(4-methylphenyl)-1H-imidazol-3-ium bromide
  参考文献：
  名称：

  Synthesis and biological evaluation of N-heterocyclic carbene–silver(I) acetate complexes derived from 4,5-ditolyl-imidazole

  摘要：

  From the reaction of 1,2-bis-(4-methylphenyl) ethane-1,2-dione with formamide, symmetrically substituted 4,5-bis-(4-methylphenyl)-1H-imidazole (1) was synthesised and further reacted with p-benzyl substituted halides to give the symmetrically substituted N-heterocyclic carbene (NHC) precursors 1a-e.The NHC precursors were then reacted with silver(I) acetate to yield NHC-silver(I) acetate complexes 1,3-bis-(benzyl)-4,5-bis-(4-methylphenyl)-imidazole-2-ylidene silver(I) acetate (2a), 1,3-bis-(4-methylbenzyl)-4,5-bis-(4-methylphenyl)-imidazole-2-ylidene silver(I) acetate (2b), 1,3-bis-(4-methoxylbenzyl)-4, 5-bis-(4-methylphenyl)-imidazole-2-ylidene silver(I) acetate (2c), 1,3-bis-(4-methoxycarbonylbenzyl)-4, 5-bis-(4-methylphenyl)-imidazole-2-ylidene silver(I) acetate (2d) and 1,3-bis-(4-cyanobenzyl)-4,5-bis-(4-methylphenyl)-imidazole-2-ylidene silver(I) acetate (2e).Two NHC-silver acetate complexes 2a and 2e were characterised by single crystal X-ray diffraction. The preliminary in vitro antibacterial activity of the NHC-silver complexes 2a-e was investigated against Gram-positive bacteria Staphylococcus aureus and Gram-negative bacteria Escherichia coli using the qualitative Kirby-Bauer disk-diffusion method. The areas of clearance determined for the maximum dose (4.3 mu M) range between 1 mm and 7 mm for MSSA and 0 mmand 7 mm for E. coli. All of the newly synthesised silver(I) acetate complexes were tested for their cytotoxicity by MTT based in vitro tests on the human renal cancer cell line Caki-1 and human breast cancer cell line MCF-7 in order to determine their IC50 values. The NHC-silver complexes 2a-e were found to have IC50 values of 3.0 (+/-0.6), 0.51 (+/-0.07), 4.2 (+/-1.2), 9.0 (+/-0.6), 26 (+/-2) mu M, against the renal cancer cell-line Caki-1 and IC50 values of 2.3 (+/-0.4), 1.4 (+/-0.2), 3.0 (+/-0.5), 3.4 (+/-1.2) and 14 (+/-2) mu M against the breast cancer cell line MCF-7, respectively. Compared to our lead compound SBC3 (1,3-bisbenzyl-4,5-bisphenyl-imidazole-2-ylium silver(I) acetate) (IC50 value = 14 (+/-1) mu M against Caki-1 and 5.8 (+/-0.6) mu M against MCF-7) these values represent improved cytotoxicity against both cell lines, especially for the silver complexes 2a and 2b. These two compounds are not only more active than SBC3 but also exhibit in the case of 2b a 7 times higher biological activity than cisplatin (IC50 value = 3.3 mu M) against Caki-1. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.10.029

文献信息

• Synthesis and cytotoxicity studies of p-benzyl substituted NHC–copper(I) bromide derivatives
  作者：Wojciech Streciwilk、Frauke Hackenberg、Helge Müller-Bunz、Matthias Tacke

  DOI：10.1016/j.poly.2013.11.039

  日期：2014.9