3-hydroxy-4-methoxyxanthone | 58315-65-4

• 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: 3-hydroxy-4-methoxyxanthone
• 英文别名: 3-hydroxy-4-methoxy-9H-xanthen-9-one；6-hydroxy-5-methoxyxanthone；3-Hydroxy-4-methoxyxanthon；3-Hydroxy-4-methoxyxanthen-9-one
• CAS: 58315-65-4
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: WRPFBSLWEKZESU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-methoxyxanthone 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 3-Benzyloxy-4-methoxy-9-oxo-9H-xanthene-2-carboxylic acid
  参考文献：
  名称：

  单、二、三和四取代氧杂蒽酮的 1H 和 13C NMR 光谱

  摘要：

  24种不同取代模式的氧杂蒽酮的结构解析是通过光谱方法进行的，即二维核磁共振技术，如相关光谱（COSY）、核奥弗豪泽效应（NOE）、异核相关（HETCOR）和一维核磁共振技术、选择性不敏感核通过极化转移 (INEPT) 增强。© 1997 约翰威利父子公司。

  DOI：

  10.1002/(sici)1097-458x(199804)36:4<305::aid-omr193>3.0.co;2-n
• 作为产物：
  描述：

  3,4-dimethoxyxanthen-9-one 在 2-二乙氨基乙硫醇盐酸盐 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以46%的产率得到3-hydroxy-4-methoxyxanthone
  参考文献：
  名称：

  Pyranoxanthones: Synthesis, growth inhibitory activity on human tumor cell lines and determination of their lipophilicity in two membrane models

  摘要：

  The benzopyran and dihydrobenzopyran moieties can be considered as "privileged motifs" in drug discovery being good platforms for the search of new bioactive compounds. These moieties are commonly found fused to the xanthonic scaffold belonging to the biologically important family of the generally designated prenylated xanthones. Several pyranoxanthones have shown promising antitumor activity and since most of them are from natural origin, the biosynthetic pathway only allows a particular pattern of substitution which limits their structural diversity and renders any broad structure activity study hard to be established. Accordingly, with the aim of rationalizing the importance of the fused ring orientation and oxygenation pattern in pyranoxanthones, this study describes the synthesis of 14 new pyranoxanthones and evaluation of their cell growth inhibitory activity in four human tumor cell lines as well as their lipophilicity in two membrane models. This systematic approach allowed establishing structure activity and structure lipophilicity relationships for the obtained compounds in combination with 6 previously described compounds. From this work an angular pyranoxanthone scaffold emerged as particularly promising, presenting a potent cell growth inhibitory activity and suitable drug-like lipophilicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.012

文献信息

• Enantioselectivity of Chiral Derivatives of Xanthones in Virulence Effects of Resistant Bacteria
  作者：Fernando Durães、Sara Cravo、Joana Freitas-Silva、Nikoletta Szemerédi、Paulo Martins-da-Costa、Eugénia Pinto、Maria Elizabeth Tiritan、Gabriella Spengler、Carla Fernandes、Emília Sousa、Madalena Pinto

  DOI：10.3390/ph14111141

  日期：——

  Antimicrobial peptides are one of the lines of defense produced by several hosts in response to bacterial infections. Inspired by them and recent discoveries of xanthones as bacterial efflux pump inhibitors, chiral amides with a xanthone scaffold were planned to be potential antimicrobial adjuvants. The chiral derivatives of xanthones were obtained by peptide coupling reactions between suitable xanthones with enantiomerically pure building blocks, yielding derivatives with high enantiomeric purity. Among 18 compounds investigated for their antimicrobial activity against reference strains of bacteria and fungi, antibacterial activity for the tested strains was not found. Selected compounds were also evaluated for their potential to inhibit bacterial efflux pumps. Compound (R,R)-8 inhibited efflux pumps in the Gram-positive model tested and three compounds, (S,S)-8, (R)-17 and (R,S)-18, displayed the same activity in the Gram-negative strain used. Studies were performed on the inhibition of biofilm formation and quorum-sensing, to which the enantiomeric pair 8 displayed activity for the latter. To gain a better understanding of how the active compounds bind to the efflux pumps, docking studies were performed. Hit compounds were proposed for each activity, and it was shown that enantioselectivity was noticeable and must be considered, as enantiomers displayed differences in activity.

  抗菌肽是一种由多种宿主产生的防御线之一，用于应对细菌感染。受到它们的启发以及最近发现的黄酮类化合物作为细菌外排泵抑制剂，我们计划设计具有黄酮骨架的手性酰胺作为潜在的抗菌辅助剂。通过适当的黄酮与对映异构纯的构建块进行肽偶联反应，获得了黄酮的手性衍生物，产物的对映纯度较高。在对18种化合物进行抗菌活性研究时，针对细菌和真菌的参考菌株，未发现对测试菌株的抗菌活性。还评估了选择性化合物对抑制细菌外排泵的潜力。化合物(R,R)-8抑制了测试的革兰氏阳性模型中的外排泵，而三种化合物(S,S)-8、(R)-17和(R,S)-18在使用的革兰氏阴性菌株中显示了相同的活性。对生物膜形成和群体感应的抑制研究表明，对映异构体8对后者显示了活性。为了更好地了解活性化合物如何与外排泵结合，进行了对接研究。对于每种活性提出了命中化合物，并且显示出对映选择性是显著的，必须予以考虑，因为对映异构体在活性上显示出差异。