2-ethyl-1,3-bis(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: 2-ethyl-1,3-bis(naphthalen-2-ylmethyl)imidazolium bromide
• 英文别名: 2-Ethyl-1,3-bis(naphthalen-2-ylmethyl)imidazol-1-ium;bromide；2-ethyl-1,3-bis(naphthalen-2-ylmethyl)imidazol-1-ium;bromide
• 化学式: Br*C₂₇H₂₅N₂
• 分子量: 457.413
• InChiKey: OLUCUTFMANWUMO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  2-乙基咪唑 、 2-溴甲基萘 在 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 2-ethyl-1,3-bis(naphthalen-2-ylmethyl)imidazolium bromide
  参考文献：
  名称：

  Synthesis, characterization, in vitro SAR and in vivo evaluation of N,N′bisnaphthylmethyl 2-alkyl substituted imidazolium salts against NSCLC

  摘要：

  Alkyl- and N,N'-bisnaphthyl-substituted imidazolium salts were tested in vitro for their anti-cancer activity against four non-small cell lung cancer cell lines(NCI-H460, NCI-H1975, HCC827, A549). All compounds had potent anticancer activity with 2 having IC50 values in the nanomolar range for three of the four cell lines, a 17-fold increase in activity against NCI-H1975 cells when compared to cisplatin. Compounds 1-4 also showed high anti-cancer activity against nine NSCLC cell lines in the NCI-60 human tumor cell line screen. In vitro studies performed using the Annexin V and JC-1 assays suggested that NCI H460 cells treated with 2 undergo an apoptotic cell death pathway and that mitochondria could be the cellular target of 2 with the mechanism of action possibly related to a disruption of the mitochondrial membrane potential. The water solubilities of 1-4 was over 4.4 mg/mL using 2-hydroxypropyl-beta-cyclodextrin as a chemical excipient, thereby providing sufficient solubility for systemic administration. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.01.035

文献信息

• Synthesis, characterization, in vitro SAR and in vivo evaluation of N,N′bisnaphthylmethyl 2-alkyl substituted imidazolium salts against NSCLC
  作者：Michael A. DeBord、Marie R. Southerland、Patrick O. Wagers、Kristin M. Tiemann、Nikki K. Robishaw、Kyle T. Whiddon、Michael C. Konopka、Claire A. Tessier、Leah P. Shriver、Sailaja Paruchuri、David A. Hunstad、Matthew J. Panzner、Wiley J. Youngs

  DOI：10.1016/j.bmcl.2017.01.035

  日期：2017.2

  Alkyl- and N,N'-bisnaphthyl-substituted imidazolium salts were tested in vitro for their anti-cancer activity against four non-small cell lung cancer cell lines(NCI-H460, NCI-H1975, HCC827, A549). All compounds had potent anticancer activity with 2 having IC50 values in the nanomolar range for three of the four cell lines, a 17-fold increase in activity against NCI-H1975 cells when compared to cisplatin. Compounds 1-4 also showed high anti-cancer activity against nine NSCLC cell lines in the NCI-60 human tumor cell line screen. In vitro studies performed using the Annexin V and JC-1 assays suggested that NCI H460 cells treated with 2 undergo an apoptotic cell death pathway and that mitochondria could be the cellular target of 2 with the mechanism of action possibly related to a disruption of the mitochondrial membrane potential. The water solubilities of 1-4 was over 4.4 mg/mL using 2-hydroxypropyl-beta-cyclodextrin as a chemical excipient, thereby providing sufficient solubility for systemic administration. (C) 2017 Elsevier Ltd. All rights reserved.