1,3-bis(3-bromobenzyl)imidazolium bromide | 1215070-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-bis(3-bromobenzyl)imidazolium bromide
• 英文别名: 1,3-Bis-(3-bromobenzyl)imidazolium bromide；1,3-Bis[(3-bromophenyl)methyl]imidazol-1-ium;bromide
• CAS: 1215070-25-9
• 化学式: Br*C₁₇H₁₅Br₂N₂
• 分子量: 487.031
• InChiKey: ZXQYIMNIBYRIQG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  咪唑 、 3-溴苄溴 以 甲苯 为溶剂， 以32%的产率得到1,3-bis(3-bromobenzyl)imidazolium bromide
  参考文献：
  名称：

  Anti-Plasmodium activity of imidazolium and triazolium salts

  摘要：

  We have previously reported that tetrazolium salts were both potent and specific inhibitors of Plasmodium replication, and that they appear to interact with a parasite component that is both essential and conserved. The use of tetrazolium salts in vivo is limited by the potential reduction of the tetrazolium ring to form an inactive, neutral acyclic formazan. To address this issue imidazolium and triazolium salts were synthesized and evaluated as Plasmodium inhibitors. Many of the imidazolium and triazolium salts were highly potent with active concentrations in the nanomolar range in Plasmodium falciparum cultures, and specific to Plasmodium with highly favorable therapeutic ratios. The results corroborate our hypothesis that an electron-deficient core is required so that the compound may thereby interact with a negatively charged moiety on the parasite merozoite; the side groups in the compound then form favorable interactions with adjacent parasite components and thereby determine both the potency and selectivity of the compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.020

文献信息

• TRIAZOLIUM AND IMIDAZOLIUM SALTS AND USES THEREOF
  申请人：Crandall Ian E.

  公开号：US20110257235A1

  公开（公告）日：2011-10-20

  The present disclosure relates to certain new and known triazolium and/or imidazolium salts and to their therapeutic use, for example in methods of treating or preventing an infection by a Plasmodium or Babesia parasite in a subject in need thereof. The triazolium and imidazolium salts are compounds of the Formula (I) or (II): wherein R 1 -R 4 , R 1′ -R 3′ , R 8 -R 11 , X, X′, X″, Y, Y′ and Y″ are as defined in the disclosure.

  本公开涉及某些新的和已知的三唑和/或咪唑盐及其治疗用途，例如在治疗或预防受需要的主体中由Plasmodium或Babesia寄生虫引起的感染的方法中。三唑和咪唑盐是以下化合物的化合物：其中R1-R4，R1′-R3′，R8-R11，X，X′，X″，Y，Y′和Y″如本公开所定义。
• US8632914B2
  申请人：——

  公开号：US8632914B2

  公开（公告）日：2014-01-21
• Anti-Plasmodium activity of imidazolium and triazolium salts
  作者：Jason Z. Vlahakis、Carmen Lazar、Ian E. Crandall、Walter A. Szarek

  DOI：10.1016/j.bmc.2010.05.020

  日期：2010.8

  We have previously reported that tetrazolium salts were both potent and specific inhibitors of Plasmodium replication, and that they appear to interact with a parasite component that is both essential and conserved. The use of tetrazolium salts in vivo is limited by the potential reduction of the tetrazolium ring to form an inactive, neutral acyclic formazan. To address this issue imidazolium and triazolium salts were synthesized and evaluated as Plasmodium inhibitors. Many of the imidazolium and triazolium salts were highly potent with active concentrations in the nanomolar range in Plasmodium falciparum cultures, and specific to Plasmodium with highly favorable therapeutic ratios. The results corroborate our hypothesis that an electron-deficient core is required so that the compound may thereby interact with a negatively charged moiety on the parasite merozoite; the side groups in the compound then form favorable interactions with adjacent parasite components and thereby determine both the potency and selectivity of the compound. (C) 2010 Elsevier Ltd. All rights reserved.