4,5-dichloro-1,3-bis(naphthalen-2-ylmethyl)imidazolium bromide | 1215070-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-dichloro-1,3-bis(naphthalen-2-ylmethyl)imidazolium bromide
• 英文别名: 1,3-bis(naphthalen-3-ylmethyl)imidazolium bromide；1,3-bis[(naphthalen-2-yl)methyl]imidazolium bromide；1,3-Bis(naphthalen-2-ylmethyl)imidazolium bromide；1,3-bis(naphthalen-2-ylmethyl)imidazol-1-ium;bromide
• CAS: 1215070-19-1
• 化学式: Br*C₂₅H₂₁N₂
• 分子量: 429.359
• InChiKey: DAHUBBSYARTGPQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,5-dichloro-1,3-bis(naphthalen-2-ylmethyl)imidazolium bromide 、 cucurbit[8]uril 以 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Emerging Two-Dimensional Crystallization of Cucurbit[8]uril Complexes: From Supramolecular Polymers to Nanofibers

  摘要：

  The binding of imidazolium salts to cucurbit[8]uril, CB[8], triggers a stepwise self-assembly process with semiflexible polymer chains and crystalline nanostructures as early- and late-stage species, respectively. In such a process, which involves the crystallization of the host-guest complexes, the guest plays a critical role in directing self-assembly toward desirable morphologies. These include platelet-like aggregates and two-dimensional (2D) fibers, which, moreover, exhibit viscoelastic and lyotropic properties. Our observations provide a deeper understanding of the self-assembly of CB[8] complexes, with fundamental implications in the design of functional 2D systems and crystalline materials.

  DOI：

  10.1021/jacs.9b07506
• 作为产物：
  描述：

  2-溴甲基萘 在 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 4,5-dichloro-1,3-bis(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

• 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。
• Synthesis, characterization, and in vitro SAR evaluation of N,N′-bis(arylmethyl)-C2-alkyl substituted imidazolium salts
  作者：Michael A. DeBord、Patrick O. Wagers、Steven R. Crabtree、Claire A. Tessier、Matthew J. Panzner、Wiley J. Youngs

  DOI：10.1016/j.bmcl.2016.11.075

  日期：2017.1

  A series of C2-alkyl substituted N,N′-bis(arylmethyl)imidazolium salts were synthesized, characterized, and tested for their in vitro anti-cancer activity against multiple non-small cell lung cancer cell lines by our group and the National Cancer Institute’s-60 human tumor cell line screen to establish a structure-activity relationship. Compounds are related to previously published N,N′-bis(arylmethyl)imidazolium

  我们的研究小组和美国国家癌症研究所合成，表征并测试了一系列C 2烷基取代的N，N'-双（芳基甲基）咪唑鎓盐对多种非小细胞肺癌细胞株的体外抗癌活性。癌症研究所的-60个人肿瘤细胞系筛选建立了结构-活性关系。化合物与先前发表的N，N'-双（芳基甲基）咪唑鎓盐有关，但利用了历史上的喹啉基序和阴离子效应来增加水溶性。多种衍生物具有IC 50的高抗癌活性相对于一组非小细胞肺癌细胞系，其纳摩尔值至低微摩尔范围内的值。这些衍生物中的几种具有高的水溶性，并具有有效的抗增殖特性，是未来体内异种移植研究的理想候选者，并且具有进入临床应用的巨大潜力。
• 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.
• US8632914B2
  申请人：——

  公开号：US8632914B2

  公开（公告）日：2014-01-21
• [EN] TRIAZOLIUM AND IMIDAZOLIUM SALTS AND USES THEREOF AS ANTIMALARIALS<br/>[FR] SELS DE TRIAZOLIUM ET D'IMIDAZOLIUM ET UTILISATIONS DE CEUX-CI EN TANT QU'ANTIPALUDÉENS
  申请人：UNIV HAEALTH NETWORK

  公开号：WO2010025558A1

  公开（公告）日：2010-03-11

  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 R1-R4, R1'-R3', R8-R11, X, X', X", Y, Y' and Y" are as defined in the disclosure.