1,7-Dihydroxy-9-acridon

• 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: 1,7-Dihydroxy-9-acridon
• 英文别名: 1,7-dihydroxy-9(10H)-acridinone；1,7-Dihydroxyacridone；1,7-dihydroxy-10H-acridin-9-one
• 化学式: C₁₃H₉NO₃
• 分子量: 227.219
• InChiKey: KXKWBGSBYIZPDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯-6-甲氧基苯甲酸 在 PPA 、 氢溴酸 、 铜 、 potassium carbonate 、 potassium iodide 作用下， 反应 14.0h， 生成 1,7-Dihydroxy-9-acridon
  参考文献：
  名称：

  Reisch, Johannes; Probst, Wiltrud, Archiv der Pharmazie, 1987, vol. 320, # 10, p. 1065 - 1072

  摘要：

  DOI：

文献信息

• 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.
• REISCH, JOHANNES;PROBST, WILTRUD, ARCH. PHARM., 320,(1987) N 10, 1065-1072
  作者：REISCH, JOHANNES、PROBST, WILTRUD

  DOI：——

  日期：——
• Reisch, Johannes; Probst, Wiltrud, Archiv der Pharmazie, 1987, vol. 320, # 10, p. 1065 - 1072
  作者：Reisch, Johannes、Probst, Wiltrud

  DOI：——

  日期：——