3,4,5,6-tetrahydroxy-9H-xanthen-9-one | 99420-08-3

• 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: 3,4,5,6-tetrahydroxy-9H-xanthen-9-one
• 英文别名: 3,4,5,6-tetrahydroxyxanthone；3,4,5,6-tetrahydroxy-xanthen-9-one；3,4,5,6-Tetrahydroxy-xanthen-9-on；3,4,5 ,6-tetrahydroxyxanthone；3,4,5,6-tetrahydroxyxanthen-9-one
• CAS: 99420-08-3
• 化学式: C₁₃H₈O₆
• 分子量: 260.203
• InChiKey: MUWSBAZQOGXKJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,5,6-tetrahydroxy-9H-xanthen-9-one 生成 3,4,5,6-tetramethoxy-xanthen-9-one
  参考文献：
  名称：

  Shah; Shah, Journal Of Scientific and Industrial Research, 1956, vol. 15 B, p. 630,632

  摘要：

  DOI：
• 作为产物：
  描述：

  双(2,3,4-三羟基苯基)甲酮 在 sodium acetate 作用下， 以 水 为溶剂， 反应 0.25h， 以94%的产率得到3,4,5,6-tetrahydroxy-9H-xanthen-9-one
  参考文献：
  名称：

  Microwave-Assisted Efficient and Green Synthesis of Hydroxyxanthone in Water

  摘要：

  An efficient and green procedure has been developed for the synthesis of hydroxyxanthones from substituted 2,2'-dihydroxybenzophenone precursors via microwave-assisted base-catalyzed cyclization in water. This method provides excellent yields of products in a short time, making it a useful strategy for the synthesis of structurally diverse hydroxyxanthones.

  DOI：

  10.1080/00397911.2011.573170

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。
• γ-Pyrone Compounds. II: Synthesis and Antiplatelet Effects of Tetraoxygenated Xanthones
  作者：Chun-Nan Lin、Shorong-Shii Liou、Feng-Nien Ko、Che-Ming Teng

  DOI：10.1002/jps.2600811114

  日期：1992.11

  methanol. Both 3,4,6,7- and 2,3,6,7-tetrahydroxyxanthone tetraacetate showed potent anti-platelet aggregation effects on arachidonic acid-induced platelet aggregation. 3,4,6,7-Tetrahydroxyxanthone tetraacetate and 1,3,5,6-tetrahydroxyxanthone showed potent and significant anti-platelet aggregation effects on collagen-induced platelet aggregation.

  甲硫酚及其类似物1,3,5,6-，3,4,5,6-，3,4,6,7-和2,3,6,7-四羟基黄酮是由二苯甲酮前体通过Friedel-进行酰化反应，然后进行碱催化的环化反应以消除甲醇。3,4,6,7-和2,3,6,7-四羟基黄酮四乙酸盐对花生四烯酸诱导的血小板聚集均显示出有效的抗血小板聚集作用。3,4,6,7-四羟基黄酮四乙酸盐和1,3,5,6-四羟基黄酮对胶原蛋白诱导的血小板聚集表现出有效且显着的抗血小板聚集作用。
• Xanthone analogs for treating infectious diseases and complexation of heme and porphyrins
  申请人：——

  公开号：US20020055644A1

  公开（公告）日：2002-05-09

  Therapeutic compounds and compositions for the treatment of infectious diseases are disclosed. The compounds are xanthones and xanthone derivatives, such as 3,5-bis-&egr;-(N,N-diethylamino)amyloxyxanthone. The described compositions include such compounds and a pharmaceutical carrier. These compositions also can include additional materials conventionally used to form therapeutic compositions. 3,5-bis-&egr;-(N,N-diethylamino)amyloxyxanthone has an IC 50 for Plasmodium falciparum of about 0.15 &mgr;M, and an IC 50 for Leishmania mexicana of <<0.5 &mgr;M. These compositions are additionally useful for forming soluble complexes with heme and porphyrins.

  本文披露了用于治疗传染病的治疗化合物和组合物。这些化合物是黄酮和黄酮衍生物，例如3,5-双-&egr;-(N,N-二乙基氨基)戊氧基黄酮。所述组合物包括这些化合物和药用载体。这些组合物还可以包括传统用于形成治疗组合物的其他材料。3,5-双-&egr;-(N,N-二乙基氨基)戊氧基黄酮在恶性疟原虫的IC50约为0.15 &mgr;M，在墨西哥利什曼原虫的IC50为<<0.5 &mgr;M。这些组合物还可用于形成与血红素和卟啉的可溶性复合物。
• Rapid quantitative assay to measure CFTR function in a primary intestinal culture model
  申请人：UMC Utrecht Holding B.V.

  公开号：US10006904B2

  公开（公告）日：2018-06-26

  The invention relates to an assay for diagnosing a disease or affliction that affects fluid uptake or secretion or for studying the effectiveness of one or more drugs for treating the disease or affliction, wherein the assay comprises measuring swelling of one or more organoids.

  本发明涉及一种检测方法，用于诊断影响液体吸收或分泌的疾病或痛苦，或研究一种或多种治疗疾病或痛苦的药物的有效性，其中检测方法包括测量一种或多种有机体的肿胀。
• Identifying drug candidates for treating polycystic kidney disease using organoids generated from primary cells
  申请人：UMC Utrecht Holding B.V.

  公开号：US11035852B2

  公开（公告）日：2021-06-15

  The invention relates to an assay for diagnosing a disease or affliction that affects fluid uptake or secretion or for studying the effectiveness of one or more drugs for treating the disease or affliction, wherein the assay comprises measuring swelling of one or more organoids.

  本发明涉及一种检测方法，用于诊断影响液体吸收或分泌的疾病或痛苦，或研究一种或多种治疗疾病或痛苦的药物的有效性，其中检测方法包括测量一种或多种有机体的肿胀。