N-(6-(diethylamino)-9-(2-(4-(prop-2-yn-1-yl)piperazine-1-carbonyl)phenyl)-3H-xanthen-3-ylidene)-N-ethylethanaminium | 1309434-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(6-(diethylamino)-9-(2-(4-(prop-2-yn-1-yl)piperazine-1-carbonyl)phenyl)-3H-xanthen-3-ylidene)-N-ethylethanaminium
• 英文别名: rhodamine B 4-(propargyl)piperazine amide；[6-(Diethylamino)-9-[2-(4-prop-2-ynylpiperazine-1-carbonyl)phenyl]xanthen-3-ylidene]-diethylazanium；[6-(diethylamino)-9-[2-(4-prop-2-ynylpiperazine-1-carbonyl)phenyl]xanthen-3-ylidene]-diethylazanium
• CAS: 1309434-53-4
• 化学式: C₃₅H₄₁N₄O₂
• 分子量: 549.736
• InChiKey: ZJQYABKZWZCBIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  39
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(6-(diethylamino)-9-(2-(4-(prop-2-yn-1-yl)piperazine-1-carbonyl)phenyl)-3H-xanthen-3-ylidene)-N-ethylethanaminium 、 4-叠氮基-2,2,6,6-四甲基-1-哌啶基氧基 在 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以33%的产率得到
  参考文献：
  名称：

  [EN] NOVEL PROBES AND TARGETING COMOUNDS FOR MITOCHONDRIA
  [FR] NOUVELLES SONDES ET COMPOSÉS DE CIBLAGE DES MITOCHONDRIES

  摘要：

  公开号：

  WO2014063033A3
• 作为产物：
  描述：

  罗丹明B 在 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成 N-(6-(diethylamino)-9-(2-(4-(prop-2-yn-1-yl)piperazine-1-carbonyl)phenyl)-3H-xanthen-3-ylidene)-N-ethylethanaminium
  参考文献：
  名称：

  New cytotoxic annonaceous acetogenin mimetics having a nitrogen-heterocyclic terminal and their application to cell imaging

  摘要：

  A terminal unsaturated lactone or its equivalent is commonly believed to be essential for the cytotoxicity of natural annonaceous acetogenins and their artificial mimetics. In this work, we discovered a series of new cytotoxic ethylene glycol ether-containing mimetics, in which a variety of simple aliphatic nitrogen-heterocycles were introduced to replace the lactone terminal of AA005 (1), a representative bioactive polyether mimic identified from our previous research, for the first time. Among these, mimic 4 bearing a terminal piperazine was found to be the most potent compound against the proliferation of three cancer cells. Based on our new findings, a fluorescent probe 7 was also developed and successfully applied to the imaging of cancer cells. This work provides a new strategy for developing simpler cytotoxic mimetics of natural annonaceous acetogenins and molecular tools for biological imaging. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.047

文献信息

• Dendritic surface functionalization of biodegradable polymer assemblies
  作者：Ali Nazemi、Ryan C. Amos、Colin V. Bonduelle、Elizabeth R. Gillies

  DOI：10.1002/pola.24686

  日期：2011.6.15

  The functionalization of nanomaterials with dendritic surface moieties was recently demonstrated to be an effective means of displaying biological ligands and potentially modulating the biological properties of these materials. With the aim of extending this surface functionalization approach to biodegradable polymer assemblies, poly(ethylene oxide)‐polycaprolactone (PEO‐PCL) block copolymers with

  最近证明具有树突表面部分的纳米材料的功能化是展示生物配体和潜在地调节这些材料的生物学特性的有效手段。为了将这种表面功能化方法扩展到可生物降解的聚合物组件，制备了带有末端叠氮化物或甲氧基的聚（环氧乙烷）-聚己内酯（PEO-PCL）嵌段共聚物，并组装形成了具有不同表面叠氮化物负载量的胶束或囊泡。制备带有外围胺，胍或羟基的树突并将其缀合至组装体，并测量缀合产率，并将其作为叠氮化物负载和组装体类型（胶束与囊泡）的函数进行比较。还结合了小分子罗丹明衍生物，可以研究位阻效应。通过光散射和透射电子显微镜研究了表面功能化对组件聚集状态的影响。总的来说，结果显示出两个系统之间在反应产率和稳定性方面的有趣差异。此外，发现用带有外围胍的树突官能化的胶束相对于对照胶束表现出增强的细胞摄取，表明该方法可用于调节材料的生物学特性。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym
• New cytotoxic annonaceous acetogenin mimetics having a nitrogen-heterocyclic terminal and their application to cell imaging
  作者：Yi-Jie Chen、Sheng Jin、Jie Xi、Zhu-Jun Yao

  DOI：10.1016/j.tet.2014.05.047

  日期：2014.8

  A terminal unsaturated lactone or its equivalent is commonly believed to be essential for the cytotoxicity of natural annonaceous acetogenins and their artificial mimetics. In this work, we discovered a series of new cytotoxic ethylene glycol ether-containing mimetics, in which a variety of simple aliphatic nitrogen-heterocycles were introduced to replace the lactone terminal of AA005 (1), a representative bioactive polyether mimic identified from our previous research, for the first time. Among these, mimic 4 bearing a terminal piperazine was found to be the most potent compound against the proliferation of three cancer cells. Based on our new findings, a fluorescent probe 7 was also developed and successfully applied to the imaging of cancer cells. This work provides a new strategy for developing simpler cytotoxic mimetics of natural annonaceous acetogenins and molecular tools for biological imaging. (C) 2014 Elsevier Ltd. All rights reserved.
• [EN] NOVEL PROBES AND TARGETING COMOUNDS FOR MITOCHONDRIA<br/>[FR] NOUVELLES SONDES ET COMPOSÉS DE CIBLAGE DES MITOCHONDRIES
  申请人：UNIV MICHIGAN TECH

  公开号：WO2014063033A3

  公开（公告）日：2014-06-12