1-benzyl-4,5-dichloro-3-(naphthalen-2-ylmethyl)imidazolium bromide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-benzyl-4,5-dichloro-3-(naphthalen-2-ylmethyl)imidazolium bromide
• 英文别名: 1-Benzyl-4,5-dichloro-3-(naphthalen-2-ylmethyl)imidazolium bromide；1-benzyl-4,5-dichloro-3-(naphthalen-2-ylmethyl)imidazol-3-ium;bromide
• 化学式: Br*C₂₁H₁₇Cl₂N₂
• 分子量: 448.189
• InChiKey: RRMAFQUQWZTBAK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4,5-dichloro-1-(naphthalen-2-ylmethyl)imidazole 以 乙腈 为溶剂， 反应 8.0h， 生成 1-benzyl-4,5-dichloro-3-(naphthalen-2-ylmethyl)imidazolium bromide
  参考文献：
  名称：

  Anti-tumor activity of lipophilic imidazolium salts on select NSCLC cell lines

  摘要：

  The anti-tumor activity of imidazolium salts is highly dependent upon the substituents on the nitrogen atoms of the imidazolium cation. We have synthesized and characterized a series of naphthalene-substituted imidazolium salts and tested them against a variety of non-small-cell lung cancer cell lines. Several of these complexes displayed anticancer activity comparable to cisplatin. These compounds induced apoptosis in the NCI-H460 cell line as determined by Annexin V staining, caspase-3, and PARP cleavage. These results strongly suggest that this class of compounds can serve as potent chemotherapeutic agents.

  DOI：

  10.1007/s00044-015-1330-z

文献信息

• [EN] AZOLIUM AND PURINIUM SALT ANTICANCER AND ANTIMICROBIAL AGENTS<br/>[FR] ANTIMICROBIENS ET ANTINÉOPLASIQUES DE SELS D'AZOLIUM ET DE PURINIUM
  申请人：UNIV AKRON

  公开号：WO2012149523A1

  公开（公告）日：2012-11-01

  Singly and multiply charged imidazolium cations (ICs) have been identified as a class of chemical compositions that possess potent antineoplastic, antibacterial and antimicrobial properties. The imidazolium cations disclosed demonstrate greater or equivalent potency towards cancerous cells as the current clinical standard, cisplatin. These imidazolium cations, however, achieve this efficacy without any of the known toxic side effects caused by heavy metal-based antineoplastic drugs such as cisplatin.

  单电荷和多电荷咪唑阳离子（ICs）已被确认为一类具有强效抗肿瘤、抗菌和抗微生物特性的化学成分。所披露的咪唑阳离子对癌细胞表现出比当前临床标准顂铂更高或相等的效力。然而，这些咪唑阳离子在不引起类似顂铂等重金属抗肿瘤药物已知的毒副作用的情况下实现了这种功效。
• Anti-tumor activity of lipophilic imidazolium salts on select NSCLC cell lines
  作者：Brian D. Wright、Michael C. Deblock、Patrick O. Wagers、Ernest Duah、Nikki K. Robishaw、Kerri L. Shelton、Marie R. Southerland、Michael A. DeBord、Kortney M. Kersten、Lucas J. McDonald、Jason A. Stiel、Matthew J. Panzner、Claire A. Tessier、Sailaja Paruchuri、Wiley J. Youngs

  DOI：10.1007/s00044-015-1330-z

  日期：2015.7

  The anti-tumor activity of imidazolium salts is highly dependent upon the substituents on the nitrogen atoms of the imidazolium cation. We have synthesized and characterized a series of naphthalene-substituted imidazolium salts and tested them against a variety of non-small-cell lung cancer cell lines. Several of these complexes displayed anticancer activity comparable to cisplatin. These compounds induced apoptosis in the NCI-H460 cell line as determined by Annexin V staining, caspase-3, and PARP cleavage. These results strongly suggest that this class of compounds can serve as potent chemotherapeutic agents.