tert-butyl N-{5-[9-(6-chloro-2-methoxyacridinyl)amino]pentyl}-carbamate | 865429-61-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl N-{5-[9-(6-chloro-2-methoxyacridinyl)amino]pentyl}-carbamate
• 英文别名: tert-butyl (5-((6-chloro-2-methoxyacridin-9-yl)amino)pentyl)carbamate
• CAS: 865429-61-4
• 化学式: C₂₄H₃₀ClN₃O₃
• 分子量: 443.974
• InChiKey: BMTYNRHBJPJECZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.48
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-{5-[9-(6-chloro-2-methoxyacridinyl)amino]pentyl}-carbamate 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  [EN] ACRIDIN-9-YL-AMINE, QUINOLIN-9-YL-AMINE, 1 -AMINO-9H-THIOXANTHENE-9-ONE AND BENZO[B][1,5]NAPHTHYRI DIN-10-YL-AMINE DERIVATIVES AS AUTOPHAGY INHIBITORS FOR TREATING CANCER
  [FR] DÉRIVÉS D'ACRIDIN-9-YL-AMINE, DE QUINOLIN-9-YL-AMINE, DE 1 -AMINO-9H-THIOXANTHÈNE-9-ONE ET DE BENZO[B][1,5]NAPHTYRIDIN-10-YL-AMINE UTILSÉS COMME INHIBITEURS DE L'AUTOPHAGIE POUR LE TRAITEMENT DU CANCER

  摘要：

  本公开提供了一种脱氧胸苷-9-基胺、喹啉-9-基胺、1-氨基-9H-噻吩并[1,5]苯并并[1,5]萘啉-10-基胺衍生物和结构相关化合物，用作治疗癌症的自噬抑制剂。本描述公开了示例化合物的合成和表征，以及其药理数据（例如第77页至155页；示例1至22；化合物A；化合物1至21；表1至3）。

  公开号：

  WO2021142065A1
• 作为产物：
  描述：

  1,5-二氨基戊烷 在 苯酚 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.25h， 生成 tert-butyl N-{5-[9-(6-chloro-2-methoxyacridinyl)amino]pentyl}-carbamate
  参考文献：
  名称：

  Synthesis of Dimeric Acridine Derived Nucleic Acid Intercalators

  摘要：

  一系列抗病毒化合物由一个插入的吖啶衍生部分、一个间隔区域和一个反应性EDTA衍生的结合物组成，通过简单的序列合成。适当单保护的1,ω-烷基二胺与6,9-二氯-2-甲氧基吖啶（1）反应后去保护并与EDTA二酐发生反应，形成目标分子。在抗坏血酸存在下，MS2噬菌体的滴度降低了8个数量级。

  DOI：

  10.1515/znb-2005-0114

文献信息

• Synthesis of acridine-nuclear localization signal (NLS) conjugates and evaluation of their impact on lipoplex and polyplex-based transfection
  作者：Caroline Boulanger、Christophe Di Giorgio、Pierre Vierling

  DOI：10.1016/j.ejmech.2005.07.015

  日期：2005.12

  We report on the synthesis of various acridine(Acr)-spacer-nuclear localization signal (NLS) peptide conjugates and explore whether their use as NLS-labeling agent of plasmidic DNA could improve gene nuclear import and expression into cells when mediated by synthetic DNA complexes. As the conditions of successful use of the NLS properties to enhance gene transfer are not clear, and with the aim of detecting and defining the requirements of NLS-enhanced transfection, we investigated gene delivery and expression into various cell lines with various DNA complexes (lipoplexes or polyplexes) that were formulated for various N/P ratios from various preformed Acr-spacer-NLS/DNA complexes (1: 1, 5:1 and 10: 1 molar ratio). For the in vitro transfection assays, the lipoplexes and polyplexes were formulated from the preformed Acr-spacer-NLS/DNA complexes and dioctadecylamidoglycylspermine (DOGS)/dioleylphosphatidylethanolamine (DOPE) 1:1 mol and branched polyethyleneimine (PEI) 25 kDa, respectively, which are very efficient in vitro gene transfer systems. We show by fluorescence experiments that part of the acridine-NLS-conjugates remains intercalated within the plasmid for most of the N/P lipoplexes and polyplexes investigated. We show that, as several other studies performed with NLS-conjugates that are not covalently linked to DNA, the expression of the transgene is in most cases not improved upon complexation of plasmidic DNA with NLS-intercalating conjugates prior to its formulation as lipoplexes or polyplexes. (c) 2005 Elsevier SAS. All rights reserved.