3,7-dimethoxy-1-hydroxy-acridone

• 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: 3,7-dimethoxy-1-hydroxy-acridone
• 英文别名: 1-hydroxy-3,7-dimethoxyacridone；1-Hydroxy-3,7-dimethoxy-10H-acridin-9-one
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: WQZJIBCFNLNQOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 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：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  夫拉美诺 、 2-氨基-5-甲氧基苯甲酸 反应 0.58h， 以48%的产率得到3,7-dimethoxy-1-hydroxy-acridone
  参考文献：
  名称：

  Acridone derivatives as anti-herpesvirus agents

  摘要：

  描述了治疗疱疹病毒感染的方法。该方法涉及向需要的受试者施用下面的化合物公式I或公式II中的一种，或其药用可接受的盐，以有效治疗感染。在这些化合物中，W为N或CR5；X3和X4分别独立为O或S；Y为N、O、S或C。

  公开号：

  US20050049273A1

文献信息

• Acridone derivatives as anti-herpesvirus agents
  申请人：Bastow F. Kenneth

  公开号：US20050049273A1

  公开（公告）日：2005-03-03

  Methods of treating a herpes virus infections are described. The methods involve administering to a subject in need thereof a compound of Formula I or Formula II below: or a pharmaceutically acceptable salt thereof in an amount effective to treat the infection. In such compounds, W is N or CR 5 ; X 3 and X 4 are each independently O or S; and Y is N, O, S or C.

  描述了治疗疱疹病毒感染的方法。该方法涉及向需要的受试者施用下面的化合物公式I或公式II中的一种，或其药用可接受的盐，以有效治疗感染。在这些化合物中，W为N或CR5；X3和X4分别独立为O或S；Y为N、O、S或C。
• 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.