1,3-dihydroxy-7-fluoroxanthone | 1357085-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,3-dihydroxy-7-fluoroxanthone
• 英文别名: 7-Fluoro-1,3-dihydroxyxanthen-9-one；7-fluoro-1,3-dihydroxyxanthen-9-one
• CAS: 1357085-61-0
• 化学式: C₁₃H₇FO₄
• 分子量: 246.195
• InChiKey: KXRFVUBZRKSYGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.67
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,3-dihydroxy-7-fluoroxanthone 在 吡啶 、 盐酸 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 14.5h， 生成 N-(7-fluoro-1-hydroxy-9-oxo-9H-xanthen-3-yl)-[1,1'-biphenyl]-4-sulfonamide
  参考文献：
  名称：

  The Design and Synthesis of N-Xanthone Benzenesulfonamides as Novel Phosphoglycerate Mutase 1 (PGAM1) Inhibitors

  摘要：

  磷酸甘油酸变位酶1（PGAM1）的上调已被发现是多种癌症中的一个常见现象。抑制PGAM1为癌症治疗提供了一种新的有希望的策略。基于我们之前的工作，我们发现了一系列新的N-呫吨酮苯磺酰胺化合物作为新型PGAM1抑制剂。代表性分子15h，其IC50值为2.1 μM，与PGMI-004A相比，表现出增强的PGAM1抑制活性和更高的酶抑制特异性，同时其抗增殖活性略有提高。

  DOI：

  10.3390/molecules23061396
• 作为产物：
  描述：

  5-氟水杨酸 、 间苯二酚 在 zinc(II) chloride 、 三氯氧磷 作用下， 以5 %的产率得到1,3-dihydroxy-7-fluoroxanthone
  参考文献：
  名称：

  Hydroxy-xanthones as promising antiviral agents: Synthesis and biological evaluation against human coronavirus OC43

  摘要：

  DOI：

  10.1016/j.bmcl.2023.129211

文献信息

• 一种Hsp27抑制剂及其制备方法和药学上的应用
  申请人：香港城市大学深圳研究院

  公开号：CN117777154A

  公开（公告）日：2024-03-29

  本发明提供了一种Hsp27抑制剂及其制备方法和药学上的应用。所述Hsp27抑制剂为结构式Ⅰ所示的化合物或其药学上可接受的盐：#imgabs0#其中，n＝1、2、3或4；所述Hsp27抑制剂用于治疗与Hsp27表达量相关疾病如癌症。
• Anti-AIDS agents 85. Design, synthesis, and evaluation of 1R,2R-dicamphanoyl-3,3-dimethyldihydropyrano-[2,3-c]xanthen-7(1H)-one (DCX) derivatives as novel anti-HIV agents
  作者：Ting Zhou、Qian Shi、Chin-Ho Chen、Li Huang、Phong Ho、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1016/j.ejmech.2011.10.025

  日期：2012.1

  In this study, 1R,2R-dicamphanoyl-3,3-dimethydihydropyrano[2,3-c]xanthen-7(1H)-one (DCX) derivatives were designed and synthesized as novel anti-HIV agents against both wild-type and non-nucleoside reverse transcriptase (RT) inhibitor-resistant HIV-1 (RTMDR-1) strains. Twenty-four DCX analogs (6-29) were synthesized and evaluated against the non-drug-resistant HIV-1 NL4-3 strain, and selected analogs were also screened for their ability to inhibit the RTMDR-1 strain. Compared with the control 2-ethyl-3',4'-di-O-(-)-camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone (2-EDCP, 2), one of the best anti-HIV coumarin derivatives in our prior study, three DCX compounds (7, 12, and 22) showed better activity against both HIV strains with an EC50 range of 0.062-0.081 mu M, and five additional compounds (8, 11, 16, 18, and 21) exhibited comparable anti-HIV potency. Six DCX analogs (7, 11-12, 18, and 21-22) also showed enhanced selectivity index (SI) values in comparison to the control. Structure-activity relationship (SAR) information suggested that the extended conjugated system of the pyranoxanthone skeleton facilitates the interaction of the small DCX molecule within the viral binding pocket, consequently leading to enhanced anti-HIV activity and selectivity. Compared to DCP compounds, DCX analogs are a more promising new class of anti-HIV agents. (C) 2011 Elsevier Masson SAS. All rights reserved.