Rubraxanthone | 20245-38-9

• 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: Rubraxanthone
• 英文别名: 1,3,5-trihydroxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one；1,3,5-trihydroxy-2-(3-methylbut-2-enyl)-9H-xanthen-9-one；1,3,5-trihydroxy-2-(3-methylbut-2-enyl)-xanthone；1,3,5-trihydroxy-2-(3-methylbut-2-enyl)xanthone；2-(3,3-dimethylallyl)-1,3,5-trihydroxyxanthone；1,3,5-trihydroxy-2-prenylxanthone；2-(3-Methylbut-2-enyl)-1,3,5-trihydroxyxanthone；1,3,5-trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
• CAS: 20245-38-9
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: XEHWUYVZHDBZHK-UHFFFAOYSA-N

物化性质

• 熔点：
  280-282 °C
• 沸点：
  553.4±39.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Rubraxanthone 在 氧气 、 tetraphenylporphyrin 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以63%的产率得到1,3,5-trihydroxy-2-(2-hydroxy-3-methylbut-3-enyl)-9H-xanthen-9-one
  参考文献：
  名称：

  Synthesis of 2-hydroxy-3-methylbut-3-enyl substituted coumarins and xanthones as natural products. Application of the Schenck ene reaction of singlet oxygen with ortho-prenylphenol precursors

  摘要：

  Application of our original photooxidation-reduction methodology to prenylated dihydroxycoumarin and trihydroxyxanthone compounds led to the corresponding ortho-(2-hydroxy-3-methylbut-3-enyl)phenol derivatives with yields ranging from 8 to 65%. In most of the reported experiments, the oxidation products distribution, after the photooxygenation step, was controlled by the competition between the large group effect and the stabilising phenolic assistance effect. We also showed that ortho-(3-hydroxy-3-methylbut-1-enyl)phenol derivatives could be considered as biogenetic precursors of 2,2-dimethylbenzopyranic structures. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.033
• 作为产物：
  描述：

  2,3-二甲氧基苯甲酸 在 吡啶 、 氢氧化钾 、 三氯化铝 、 草酰氯 、 四甲基氢氧化铵 、 氢碘酸 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 62.0h， 生成 Rubraxanthone
  参考文献：
  名称：

  Synthesis of 2-hydroxy-3-methylbut-3-enyl substituted coumarins and xanthones as natural products. Application of the Schenck ene reaction of singlet oxygen with ortho-prenylphenol precursors

  摘要：

  Application of our original photooxidation-reduction methodology to prenylated dihydroxycoumarin and trihydroxyxanthone compounds led to the corresponding ortho-(2-hydroxy-3-methylbut-3-enyl)phenol derivatives with yields ranging from 8 to 65%. In most of the reported experiments, the oxidation products distribution, after the photooxygenation step, was controlled by the competition between the large group effect and the stabilising phenolic assistance effect. We also showed that ortho-(3-hydroxy-3-methylbut-1-enyl)phenol derivatives could be considered as biogenetic precursors of 2,2-dimethylbenzopyranic structures. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.033

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• 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。
• Regiospecific Prenylation of Hydroxyxanthones by a Plant Flavonoid Prenyltransferase
  作者：Ruishan Wang、Ridao Chen、Jianhua Li、Xiao Liu、Kebo Xie、Dawei Chen、Ying Peng、Jungui Dai

  DOI：10.1021/acs.jnatprod.6b00417

  日期：2016.8.26

  prenyltransferase with substrate flexibility from Morus alba, is demonstrated. Among the enzymatic products, 2-dimethylallyl-1,3,7-trihydroxyxanthone (3a) effectively attenuated glutamate-induced injury in SK-N-SH neuroblastoma cells. These results suggest a potential approach for the synthesis of bioactive prenylated xanthones by a substrate-relaxed flavonoid prenyltransferase.

  C-烯丙基化的氧杂蒽酮是分布在植物和微生物中的具有药理吸引力的专门代谢产物。氧杂蒽的异戊烯基化通常有助于这些化合物的结构多样性和生物活性。然而，有效的氧杂蒽酮的区域特异性异戊烯化仍然具有挑战性。在这项研究中，一些结构上不同的hydroxyxanthones（的的区域专一性异戊烯化3 - 10）由MaIDT，植物类黄酮异戊二烯基转移酶与来自基板的灵活性桑白皮，是证明。在酶促产物中，2-二甲基烯丙基-1,3,7-三羟基黄酮（3a）有效减轻了SK-N-SH神经母细胞瘤细胞中谷氨酸诱导的损伤。这些结果表明通过底物松弛的类黄酮异戊二烯基转移酶合成生物活性的烯丙基化的氧杂蒽的潜在方法。
• Xanthones and triterpenes of Calophyllum tomentosum
  作者：Subadra Karunanayake、Subramanian Sotheeswaran、M. Uvais、S. Sultanbawa、Sinnathamby Balasubramaniam

  DOI：10.1016/0031-9422(81)80026-x

  日期：1981.1
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).