1,6-dimethoxyacridin-9(10H)-one | 71014-61-4

• 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: 1,6-dimethoxyacridin-9(10H)-one
• 英文别名: 1,6-dimethoxy-10H-acridin-9-one
• CAS: 71014-61-4
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: BASNPBWSEMMNNH-UHFFFAOYSA-N

物化性质

• 熔点：
  279-280 °C
• 沸点：
  449.5±45.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-dimethoxyacridin-9(10H)-one 在 氢溴酸 作用下， 反应 10.0h， 以66%的产率得到1,6-dihydroxy-10H-acridin-9-one
  参考文献：
  名称：

  Structure–activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth

  摘要：

  A series of N-unsubstituted hydroxy-10H-acridin-9-ones were synthesized and evaluated for inhibitory action against HaCaT keratinocyte growth, in order to explore their potential as antipsoriatic agents. For structure activity relationship studies, the number and position of the hydroxyl groups were modified, the oxygen functions substituted or replaced, or additional functional groups were introduced into the acridone scaffold. 1,8-Dihydroxy-10H-acridin-9-one (4), which is an aza-analogue of the antipsoriatic anthralin, was only marginally active. However, 1,3-dihydroxy-substituted 5ee was the most potent acridone within this series and inhibited keratinocyte growth with an IC(50) value comparable to that of anthralin. In contrast to anthralin, nearly all members of the acridone series were devoid of radical generating properties, which were determined by their capability to interact with the free radical 2,2-diphenyl-1-picrylhydrazyl. Structures with a phenolic hydroxyl or an aromatic amine arranged ortho or para to the acridone NH group were exceptions. Also in contrast to anthralin, membrane-damaging effects as documented by the release of lactate dehydrogenase into the culture medium were not observed for acridones. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.013
• 作为产物：
  描述：

  在 七氟丁酸 、 氧气 作用下， 反应 2.5h， 生成 1,6-dimethoxyacridin-9(10H)-one
  参考文献：
  名称：

  Directed metalation of tertiary benzamides. Ortho N-aryl amination and synthesis of acridones

  摘要：

  DOI：

  10.1021/ja00384a064

文献信息

• A short efficient route to acronycine and other acridones
  作者：Stephen Horne、Russell Rodrigo

  DOI：10.1039/c39910001046

  日期：——

  A Fries type of rearrangement of N-tosyl-o-iodobenzanilides, triggered by lithium–iodine exchange at low temperature is the key step in a general, regiospecific synthesis of acridones.

  一种以锂–碘交换为触发的低温重排反应，对N-托烯磺酰-o-碘苯乙酰胺进行Fries类型的重排反应，是一种普遍的区域选择性合成氨基酸的关键步骤。
• Acridinium-Based Photocatalysts: A Sustainable Option in Photoredox Catalysis
  作者：Amruta Joshi-Pangu、François Lévesque、Hudson G. Roth、Steven F. Oliver、Louis-Charles Campeau、David Nicewicz、Daniel A. DiRocco

  DOI：10.1021/acs.joc.6b01240

  日期：2016.8.19

  The emergence of visible light photoredox catalysis has enabled the productive use of lower energy radiation, leading to highly selective reaction platforms. Polypyridyl complexes of iridium and ruthenium have served as popular photocatalysts in recent years due to their long excited state lifetimes and useful redox windows, leading to the development of diverse photoredox-catalyzed transformations. The low abundances of Ir and Ru in the earth's crust and, hence, cost make these catalysts nonsustainable and have limited their application in industrial-scale manufacturing. Herein, we report a series of novel acridinium salts as alternatives to iridium photoredox catalysts and show their comparability to the ubiquitous [Ir(dF-CF3-ppy)(2)(dtbpy)](PF6).
• IWAO, M.;REED, J. N.;SNIECKUS, V., J. AMER. CHEM. SOC., 1982, 104, N 20, 5531-5533
  作者：IWAO, M.、REED, J. N.、SNIECKUS, V.

  DOI：——

  日期：——
• Structure–activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth
  作者：Aleksandar Putic、Lambert Stecher、Helge Prinz、Klaus Müller

  DOI：10.1016/j.ejmech.2010.04.013

  日期：2010.8

  A series of N-unsubstituted hydroxy-10H-acridin-9-ones were synthesized and evaluated for inhibitory action against HaCaT keratinocyte growth, in order to explore their potential as antipsoriatic agents. For structure activity relationship studies, the number and position of the hydroxyl groups were modified, the oxygen functions substituted or replaced, or additional functional groups were introduced into the acridone scaffold. 1,8-Dihydroxy-10H-acridin-9-one (4), which is an aza-analogue of the antipsoriatic anthralin, was only marginally active. However, 1,3-dihydroxy-substituted 5ee was the most potent acridone within this series and inhibited keratinocyte growth with an IC(50) value comparable to that of anthralin. In contrast to anthralin, nearly all members of the acridone series were devoid of radical generating properties, which were determined by their capability to interact with the free radical 2,2-diphenyl-1-picrylhydrazyl. Structures with a phenolic hydroxyl or an aromatic amine arranged ortho or para to the acridone NH group were exceptions. Also in contrast to anthralin, membrane-damaging effects as documented by the release of lactate dehydrogenase into the culture medium were not observed for acridones. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Directed metalation of tertiary benzamides. Ortho N-aryl amination and synthesis of acridones
  作者：M. Iwao、J. N. Reed、V. Snieckus

  DOI：10.1021/ja00384a064

  日期：1982.10