1,3,5-trihydroxy-9(10H)-acridinone | 85990-00-7

• 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: 1,3,5-trihydroxy-9(10H)-acridinone
• 英文别名: 1,3,5-trihydroxy-9-acridone；1,3,5-trihydroxyacridone；1,3,5-trimethoxyacridone；1,3,5-Trihydroxyacridin-9(10H)-one；1,3,5-trihydroxy-10H-acridin-9-one
• CAS: 85990-00-7
• 化学式: C₁₃H₉NO₄
• 分子量: 243.219
• InChiKey: QCNWCELEAMCXOV-UHFFFAOYSA-N

物化性质

• 沸点：
  514.9±29.0 °C(Predicted)
• 密度：
  1.580±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 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：
  89.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3,5-trihydroxy-9(10H)-acridinone 在 三氟化硼乙醚 、 碳酸氢钠 、 potassium carbonate 、 sodium iodide 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 26.0h， 生成 3,5-Dibenzyloxy-1-hydroxy-2,4-bis(3,3-dimethylallyl)acridone
  参考文献：
  名称：

  Ramesh, Kakarla; Kapil, R. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 684 - 687

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-dihydroxy-5-methoxy-9(10H)-acridinone 在 硫酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 24.0h， 生成 1,3,5-trihydroxy-9(10H)-acridinone
  参考文献：
  名称：

  Ramesh, Kakarla; Kapil, R. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 684 - 687

  摘要：

  DOI：

文献信息

• Synthesis of acrimarins from 1,3,5-trioxygenated-9-acridone derivatives
  作者：H. M. T. B. Herath、K. Müller、H. V. K. Diyabalanage

  DOI：10.1002/jhet.5570410104

  日期：2004.1

  1,3,5-Trihydroxy-9(10H)-acridinone (1) was prepared from 3-hydroxyanthranillic acid with phloroglucinol. 1,3-Dihydroxy-5-methoxy-9(10H)-acridinone (2) was prepared from 3-methoxyanthranillic acid and phloroglucinol. Methylation of 1 under different conditions gave 1-hydroxy-3,5-dimethoxy (3), 1-hydroxy-3,5-dimethoxy-10-methyl (4), 1-hydroxy-3,5-dimethoxy-4-methyl (5), 1,3,5-trimethoxy-10-methyl (6)

  由3-羟基邻氨基苯甲酸与间苯三酚制备1,3,5-三羟基-9（10 H）-ac啶酮（1）。由3-甲氧基蒽酸和间苯三酚制备1，3-二羟基-5-甲氧基-9（10 H）-ac啶酮（2）。在不同条件下1的甲基化得到1-羟基-3,5-二甲氧基（3），1-羟基-3,5-二甲氧基-10-甲基（4），1-羟基-3,5-二甲氧基-4-甲基（5），1,3,5-三甲氧基-10-甲基（6）和1,3,5-三甲氧基-4,10-二甲基（7）类似物。4的脱甲基得到1,3,5-三羟基-10-甲基类似物8。E烯1，2，3和4分别与E-丁烯醇（9）缩合得到4种新的Acrimarins（ac啶酮-香豆素二聚体）10，11 ，分别为12和13，而，啶酮8先前曾报道过acrimarin-G（14）。
• Structure and synthesis of atalaphylline and related alkaloids
  作者：M.H. Bahar、J.D. Shringarpure、G.H. Kulkarni、B.K. Sabata

  DOI：10.1016/0031-9422(82)83108-7

  日期：1982.1

  Abstract The structure of atalaphylline, ( 1 ; 1,3,5-trihydroxy-4-(γ,γ-dimethylallyl)acridone an alkaloid of Atalantia monophylla , was confirmed by oxidative degradation and by total synthesis. The synthesis involved the preparation of 1,3,5-trihydroxy-9-acridone followed by direct prenylation to give atalaphylline and a monoprenylated product.

  摘要 通过氧化降解和全合成证实了阿塔拉茶碱( 1 ; 1,3,5-三羟基-4-(γ,γ-二甲基烯丙基)吖啶酮的结构)。 ,3,5-三羟基-9-吖啶酮，然后直接异戊二烯化，得到阿特拉茶碱和单异戊二烯化产物。
• 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.
• Bahar, M. H.; Sabata, B. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 863 - 865
  作者：Bahar, M. H.、Sabata, B. K.

  DOI：——

  日期：——
• BAHAR, M. H.;SABATA, B. K., INDIAN J. CHEM., 26,(1987) N 9, 863-865
  作者：BAHAR, M. H.、SABATA, B. K.

  DOI：——

  日期：——