1,3,5-三羟基-2,4-双(3-甲基-2-丁烯基)氧杂蒽酮 | 33390-41-9

• 物质功能分类: 天然产物 - 氧杂蒽酮
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 1,3,5-三羟基-2,4-双(3-甲基-2-丁烯基)氧杂蒽酮
• 英文名称: 8-deoxygartanin
• 英文别名: 1,3,5-trihydroxy-2,4-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one；1,3,5-trihydroxy-2,4-bis(3-methylbut-2-enyl)-9H-xanthen-9-one；8-desoxygartanin；1,3,5-trihydroxy-2,4-bis-(3-methyl-but-2-enyl)-xanthen-9-one；1,3,5-trihydroxy-2,4-bis(3-methylbut-2-enyl)xanthen-9-one
• CAS: 33390-41-9
• 化学式: C₂₃H₂₄O₅
• 分子量: 380.441
• InChiKey: GVQOVMKBYJKZSY-UHFFFAOYSA-N

物化性质

• 熔点：
  165-167 °C
• 沸点：
  595.7±50.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

制备方法与用途

生物活性

8-Deoxygartanin 是山竹果中的一种去甲基戊烯吡喃香豆素。它是一种选择性丁基胆碱酯酶 (BChE) 抑制剂，并且具有抗疟原虫活性，对 Plasmodium falciparum W2 植株的 IC50 值为 11.8 μM。此外，8-Deoxygartanin 还能抑制 NF-κB (p65) 的活化，IC50 值为 11.3 μM。

靶点

| p65 | 11.3 μM (IC50) |

反应信息

• 作为反应物：
  描述：

  1,3,5-三羟基-2,4-双(3-甲基-2-丁烯基)氧杂蒽酮 在 氧气 、 tetraphenylporphyrin 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以21%的产率得到6,11-dihydroxy-5-(2-hydroxy-3-methylbut-3-enyl)-3,3-dimethyl-3H,7H-pyrano[2,3-c]-xanthen-7-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-hydroxy-2',3,4',6'-tetramethoxybenzophenone 在 吡啶 、 氢氧化钾 、 四甲基氢氧化铵 、 氢碘酸 、 苯酚 作用下， 反应 44.0h， 生成 1,3,5-三羟基-2,4-双(3-甲基-2-丁烯基)氧杂蒽酮
  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

• 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。
• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。
• Xanthone-rich plant extracts or compounds therefrom for modulating diseases of the central nervous system and related disorders
  申请人：Deakin University

  公开号：US10568862B2

  公开（公告）日：2020-02-25

  The invention relates to a method of treatment and/or prophylaxis of a disease or disorder of the central nervous system comprising administering to a mammal in need thereof an effective amount of a xanthone-rich plant extract, or a compound derived from a xanthone-rich plant extract. The invention also relates to use of a xanthone-rich plant extract, or a compound derived from a xanthone-rich plant extract, in the preparation of a medicament for the treatment and/or prophylaxis of a disease or disorder of the central nervous system and to a xanthone-rich plant extract, or a compound derived from a xanthone-rich plant extract, for use in the treatment and/or prophylaxis of a disease or disorder of the central nervous system.

  本发明涉及一种治疗和/或预防中枢神经系统疾病或紊乱的方法，包括向需要的哺乳动物施用有效量的富含黄酮的植物提取物或从富含黄酮的植物提取物衍生的化合物。 本发明还涉及富含黄酮的植物提取物或由富含黄酮的植物提取物衍生的化合物在制备治疗和/或预防中枢神经系统疾病或紊乱的药物中的用途，以及富含黄酮的植物提取物或由富含黄酮的植物提取物衍生的化合物在治疗和/或预防中枢神经系统疾病或紊乱中的用途。
• BENNETT, GRAHAM J.;LEE, HIOK-HUANG;DAS, NAGARATNAM P., J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N0, C. 2671-2676
  作者：BENNETT, GRAHAM J.、LEE, HIOK-HUANG、DAS, NAGARATNAM P.

  DOI：——

  日期：——
• XANTHONE-RICH PLANT EXTRACTS OR COMPOUNDS THEREFROM FOR MODULATING DISEASES OF THE CENTRAL NERVOUS SYSTEM AND RELATED DISORDERS
  申请人：DEAKIN UNIVERSITY

  公开号：EP3110414B1

  公开（公告）日：2020-09-30