6-chloro-2-methoxy-N-benzylacridin-9-amine

• 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: 6-chloro-2-methoxy-N-benzylacridin-9-amine
• 英文别名: N-benzyl-6-chloro-2-methoxyacridin-9-amine；6-chloro-2-methoxy-N-(phenylmethyl)-9-acridinamine
• 化学式: C₂₁H₁₇ClN₂O
• 分子量: 348.832
• InChiKey: MSIOOXFOXSVHRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯-2-(4-甲氧基苯胺基)-苯甲酸 在 potassium carbonate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 3.75h， 生成 6-chloro-2-methoxy-N-benzylacridin-9-amine
  参考文献：
  名称：

  Novel synthetic acridine derivatives as potent DNA-binding and apoptosis-inducing antitumor agents

  摘要：

  Acridine derivatives have been explored as DNA-binding anticancer agents. Some derivatives show undesired pharmacokinetic properties and new derivatives need to be explored. In this work, a series of novel acridine analogues were synthesized by modifying previously unexplored linkers between the acridine and benzene groups and their antiproliferative activity and the DNA-binding ability were evaluated. Among these derivatives, compound 5c demonstrated DNA-binding capability and topoisomerase I inhibitory activity. In K562 cell lines, 5c induced apoptosis through mitochondria-dependent intrinsic pathways. These data suggested that compound 5c and other acridine derivatives with modified linkers between the acridine and benzene groups might be potent DNA-binding agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.008

文献信息

• Lewis Acid-Catalyzed Generation of CC and CN Bonds on π-Deficient Heterocyclic Substrates
  作者：Matteo Staderini、Maria Laura Bolognesi、J. Carlos Menéndez

  DOI：10.1002/adsc.201400674

  日期：2015.1.12

  to the efficient and completely regioselective generation of aromatic CC and CN bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work‐up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation

  在催化量的三氯化铟的存在下，对一系列卤化的氮杂环和不同种类的亲核试剂进行聚焦微波辐照可有效且完全区域选择性地生成芳族CC和CN键。该方法简单，快速，通用且廉价，并且可以在不使用干燥溶剂的情况下进行。大多数合成的化合物都是新化合物，在许多情况下，仅需过滤即可进行后处理。此外，这是使用路易斯酸作为催化剂在π缺陷杂环底物上进行杂芳基化，乙烯基化和胺化反应的第一个例子。
• Solvent- and chromatography-free amination of π-deficient nitrogen heterocycles under microwave irradiation. A fast, efficient and green route to 9-aminoacridines, 4-aminoquinolines and 4-aminoquinazolines and its application to the synthesis of the drugs amsacrine and bistacrine
  作者：Matteo Staderini、Nieves Cabezas、Maria Laura Bolognesi、J. Carlos Menéndez

  DOI：10.1016/j.tet.2012.11.083

  日期：2013.1

  very broad scope in terms of amine structure (aromatic, linear primary aliphatic, α-branched primary aliphatic, secondary aliphatic and diamines). Workup consisted of a simple washing with water and purification could be achieved by crystallization, avoiding the use of organic solvents in extraction and chromatographic purification steps. This protocol provides a solution to the long-standing synthetic

  在2当量苯酚的存在下，用胺对9-氯ac啶，4-氯喹啉和4-氯喹唑啉等分子混合物与胺进行聚焦微波辐照，可以实现胺化杂环的一般，快速和高产率合成，胺结构（芳族，线性伯脂肪族，α-支化伯脂肪族，仲脂肪族和二胺）。后处理包括简单的水洗和结晶纯化，避免在萃取和色谱纯化步骤中使用有机溶剂。该协议为解决长期合成问题提供了解决方案，该问题实现了一种实用有效的方法来胺化π不足的氮杂环以用于药物化学应用。
• [EN] METHODS AND COMPOSITIONS FOR TREATING VIRAL INFECTIONS IN HONEYBEES<br/>[FR] MÉTHODES ET COMPOSITIONS POUR LE TRAITEMENT D'INFECTIONS VIRALES CHEZ DES ABEILLES DOMESTIQUES
  申请人：ISRAEL STATE

  公开号：WO2016005979A1

  公开（公告）日：2016-01-14

  A method of increasing survival of viral infected honeybees, reducing viral load or protecting the honeybees from death, wherein said virus is a ssRNA virus, comprising administering to the honeybees an antiviral effective amount of an acridine derivative.
• Novel synthetic acridine derivatives as potent DNA-binding and apoptosis-inducing antitumor agents
  作者：Xuliang Lang、Lulu Li、Yuzong Chen、Qinsheng Sun、Qin Wu、Feng Liu、Chunyan Tan、Hongxia Liu、Chunmei Gao、Yuyang Jiang

  DOI：10.1016/j.bmc.2013.05.008

  日期：2013.7

  Acridine derivatives have been explored as DNA-binding anticancer agents. Some derivatives show undesired pharmacokinetic properties and new derivatives need to be explored. In this work, a series of novel acridine analogues were synthesized by modifying previously unexplored linkers between the acridine and benzene groups and their antiproliferative activity and the DNA-binding ability were evaluated. Among these derivatives, compound 5c demonstrated DNA-binding capability and topoisomerase I inhibitory activity. In K562 cell lines, 5c induced apoptosis through mitochondria-dependent intrinsic pathways. These data suggested that compound 5c and other acridine derivatives with modified linkers between the acridine and benzene groups might be potent DNA-binding agents. (C) 2013 Elsevier Ltd. All rights reserved.