1,3-dihydroxy-5-methoxy-9(10H)-acridinone | 63110-81-6

• 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-dihydroxy-5-methoxy-9(10H)-acridinone
• 英文别名: 1,3-dihydroxy-5-methoxy-9-acridone；1,3-dihydroxy-5-methoxyacridone；1,3-dihydroxy-5-methoxy-10H-acridin-9-one；1,3-Dihydroxy-5-methoxy-9-acridanon；1,3-Dihydroxy-5-methoxy-10H-acridin-9-one
• CAS: 63110-81-6
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: APIMHYYXWUCNTO-UHFFFAOYSA-N

物化性质

• 沸点：
  533.6±39.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  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：
• 作为产物：
  描述：

  间苯三酚 、 2-氨基-3-甲氧基苯甲酸 生成 1,3-dihydroxy-5-methoxy-9(10H)-acridinone
  参考文献：
  名称：

  阿特拉茶碱及相关生物碱的结构与合成

  摘要：

  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。

  DOI：

  10.1016/0031-9422(82)83108-7

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）。
• Anti-Herpes Simplex Virus Activity of Substituted 1-Hydroxyacridones
  作者：Christopher T. Lowden、Kenneth F. Bastow

  DOI：10.1021/jm030206l

  日期：2003.11.1

  5-Chloro-1,3-dihydroxyacridone, 1, is a potent and selective inhibitor of Herpes Simplex Virus Type-1 (HSV-1).(1) Substituted 1,3-dihydroxyacridones represent a new class of nonnucleoside HSV-1 inhibitors, and biochemical studies indicate a novel mechanism of action for 1, although the target is not yet defined.(2) With the goal of lead optimization, analogues of 1 were synthesized in an effort to describe the structure-activity relationships between 1 and its hypothetical binding site. Modifications of key functional groups led to the identity of several features of I that were important for activity. In the process, a more expedient and reliable synthesis of 1 and its analogues was developed. Analogues were evaluated against HSV-1 and HSV-2 using a viral plaque-elimination assay for viral inhibition of HSV-1 and HSV-2, and effects on replication of the host cell were also measured in order to assess a therapeutic index (TI) of selectivity. Several new analogues with significant antiviral activity were identified, including 5-methoxy-1,3-dihydroxyacridone (11), which inhibits replication of several HSV-2 strains with a mean ED50 of 0.7 muM and a TI range of 25-60-fold.
• 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：——