1,8-dihydroxy-9H-xanthen-9-one | 17624-02-1

• 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: 1,8-dihydroxy-9H-xanthen-9-one
• 英文别名: 1,8-dihydroxyxanthone；1,8-dihydroxy-xanthen-9-one；1,8-Dihydroxy-xanthen-9-on；1,8-Dihydroxyxanthon；1,8-Dihydroxyxanthen-9-one
• CAS: 17624-02-1
• 化学式: C₁₃H₈O₄
• 分子量: 228.204
• InChiKey: XWPUJQLPABYIPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,8-dihydroxy-9H-xanthen-9-one 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 1,8-(3,6,9,12,15-pentaoxaheptadecane-1,17-diyldioxy)xanthydrol
  参考文献：
  名称：

  Mills, Owen S.; Mooney, Nichola J.; Robinson, Peter M., Journal of the Chemical Society. Perkin transactions II, 1995, # 4, p. 697 - 706

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2',6,6'-tetramethoxydiphenylmethanol 在 sodium dichromate 、 aluminum tri-bromide 、 溶剂黄146 、 苯 作用下， 生成 1,8-dihydroxy-9H-xanthen-9-one
  参考文献：
  名称：

  Baeyer, Justus Liebigs Annalen der Chemie, 1910, vol. 372, p. 139

  摘要：

  DOI：

文献信息

• Synthesis, SAR and Biological Evaluation of Natural and Non-natural Hydroxylated and Prenylated Xanthones as Antitumor Agents
  作者：Xiaojin Zhang、Xiang Li、Suofu Ye、Yu Zhang、Lei Tao、Yuan Gao、Dandan Gong、Meiyang Xi、Huyan Meng、Mingqian Zhang、Wenlei Gao、Xiaoli Xu、Qinglong Guo、Qidong You

  DOI：10.2174/1573406411208061012

  日期：2012.9.1

  SAR analysis revealed that the anti-proliferative activity of the xanthones is substantially influenced by the position and number of attached hydroxyl and prenyl groups, and the presence of hydroxyl group ortho to the carbonyl function of xanthone scaffold contributes significantly to their cytotoxicity. The new prenylated xanthone 20 with a relatively simple structure, namely 1,3,8-trihydroxy-2-prenylxanthone

  为了探索围绕带有羟基和异戊二烯基部分的蒽酮骨架的详细结构-活性关系（SAR），已合成了29种天然和非天然羟基化和异戊烯化的氧杂蒽酮，并评估了它们对五种人的体外抗增殖活性癌细胞系，包括HepG2（肝细胞癌），HCT-116（结肠癌），A549（肺癌），BGC823（胃癌）和MDAMB-231（乳腺癌）。SAR分析表明，氧杂蒽酮的抗增殖活性受附着的羟基和异戊二烯基的位置和数量的影响很大，而与黄酮骨架的羰基功能邻位的羟基的存在显着影响了它们的细胞毒性。发现具有相对简单结构的新的异戊烯酮黄酮20，即1,3,8-三羟基-2-异戊二烯酮吨酮，对所有五个癌细胞系均表现出与α-Mangostin相当的有效抗肿瘤活性。进一步的机理研究表明，化合物20诱导HepG2细胞凋亡并导致细胞周期停滞在S期。这些结果突出了化合物20作为新型有效的广谱抗肿瘤药物未来开发的潜在新的潜在候选者。
• Selective colorimetric and fluorescent detection of HSO4− with sodium(i), magnesium(ii) and aluminium(iii) xanthone-crown ether complexes
  作者：Rui Shen、Xiaobo Pan、Huifang Wang、Lihui Yao、Jincai Wu、Ning Tang

  DOI：10.1039/b719407b

  日期：——

  Xanthone-crown ether (1) reacts with NaClO4, Mg(ClO4)2 and Al(ClO4)3 forming the one-dimensional chain dinuclear polymer [Na2·1·(ClO4)2] (2), the mononuclear complex [Mg·1·(H2O)2](ClO4)2 (3) and an interesting sandwich complex [Al·(1)2·(H2O)6](ClO4)3 (4) with different ratios of metal-to-ligand, respectively. The anion recognition experiment results show that the magnesium complex (3) is a good colorimetric and fluorescent detector for HSO4− with high sensitivity and selectivity.

  黄酮-冠醚（1）与NaClO4、Mg(ClO4)2和Al(ClO4)3反应，形成一维链状双核聚合物[Na2·1·(ClO4)2]（2）、单核复合物[Mg·1·(H2O)2](ClO4)2（3），以及一种有趣的夹心复合物[Al·(1)2·(H2O)6](ClO4)3（4），它们的金属与配体比例各不相同。阴离子识别实验结果表明，镁复合物（3）是一种高灵敏度和选择性的HSO4⁻的色谱计量和荧光检测器。
• 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
  申请人：덕산네오룩스 주식회사

  公开号：KR20220023862A

  公开（公告）日：2022-03-03

  본 발명은 화학식 1로 표시되는 화합물과, 제 1전극, 제 2전극 및 상기 제 1전극과 상기 제 2전극 사이의 유기물층을 포함하는 유기전기소자, 및 상기 유기전기소자를 포함하는 전자장치를 제공한다. 상기 유기물층에 화학식 1로 표시되는 화합물을 포함함으로써, 유기전기소자의 구동전압을 낮출 수 있고 발광 효율 및 수명을 향상시킬 수 있다.

  本发明提供了一种包括化学式1所示化合物、第1电极、第2电极以及介于所述第1电极和所述第2电极之间的有机物层的有机电子器件，以及包括所述有机电子器件的电子装置。通过在所述有机物层中包含化学式1所示的化合物，可以降低有机电子器件的驱动电压，并提高发光效率和寿命。
• Baeyer, Justus Liebigs Annalen der Chemie, 1910, vol. 372, p. 139
  作者：Baeyer

  DOI：——

  日期：——
• Synthesis and pharmacological activities of xanthone derivatives as α-glucosidase inhibitors
  作者：Yan Liu、Lan Zou、Lin Ma、Wen-Hua Chen、Bo Wang、Zun-Le Xu

  DOI：10.1016/j.bmc.2006.04.014

  日期：2006.8

  Considerable interest has been attracted in xanthone and its derivatives because of their large variety of pharmacological activities. In this project, a series of hydroxylxanthones and their aectoxy and alkoxy derivatives were synthesized and evaluated as alpha-glucosidase inhibitors, aimed at clarifying the structure-activity correlation. The results indicated that these xanthone derivatives were capable of inhibiting in vitro alpha-glucosidase with moderate to good activities. Among them, polyhydroxylxanthones exhibited the highest activities and thus may be exploitable as a lead compound for the development of potent alpha-glucosidase inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.