1,3,6-trihydroxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one | 94141-72-7

• 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: 1,3,6-trihydroxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
• 英文别名: 1,3,6-trihydroxy-2-(3-methylbut-2-enyl)-9H-xanthene-9-one；1,3,6-trihydroxy-2-(3-methylbut-2-enyl)-9H-xanthen-9-one；1,3,6-trihydroxy-2-(3-methyl-2-butenyl)xanthone；2-(3,3-dimethylallyl)-1,3,6-trihydroxyxanthone；1,3,6-Trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
• CAS: 94141-72-7
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: BUVGSDAKOBKGFK-UHFFFAOYSA-N

物化性质

• 沸点：
  570.1±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：

  1,3,6-trihydroxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 1.0h， 以0.03 g的产率得到5,9-dihydroxy-2,2-dimethyl-2H,6H-pyrano<3,2-b>xanthen-6-one
  参考文献：
  名称：

  某些1,3,6-三加氧异戊烯基氧杂蒽的合成：藤黄酮A的组成

  摘要：

  在甲醇甲醇钠的存在下，1,3-二羟基-6-甲氧基和1,3,6-三羟基黄酮与1-溴3-甲基丁-2-烯反应，得到相应的3-甲基丁-2-烯基化的氧杂蒽，描述。1,3,6-三羟基-2,4-双（3-甲基丁-2-烯基）-9H-黄嘌呤-9-的合成，设计为藤黄酮A，据报道是藤黄果皮的天然产物柿（藤黄科），也已经实现。然而，发现合成的an吨酮与天然的藤黄酮A不同，因此其构成需要重新研究。

  DOI：

  10.1016/0040-4020(84)85015-2
• 作为产物：
  描述：

  3-甲基丁-2-烯基膦酰磷酸氢酯 、 gentisein 在 recombinant plant flavonoid prenyltransferase from Morus alba 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 16.0h， 以19.1%的产率得到1,3,6-trihydroxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
  参考文献：
  名称：

  植物类黄酮类异戊二烯基转移酶对羟基黄嘌呤的区域特异性烯丙基化

  摘要：

  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。

  DOI：

  10.1021/acs.jnatprod.6b00417

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。
• Synthesis of 1,3,6-Trioxygenated Prenylated Xanthone Derivatives as Potential Antitumor Agents
  作者：Chan K. Lim、Lai-Yeng Tho、Yang M. Lim、Syed A. A. Shah、Jean-Frederic F. Weber

  DOI：10.2174/157017812802850230

  日期：2012.9.1

  To investigate the antitumor activities of xanthonic compounds, 10 prenylated xanthone derivatives 2-11 along with their key building block 1,3,6-trihydroxyxanthone 1 were evaluated for their potential cytotoxic activities against HeLa and MDA-MB-231 cancer cell lines. The synthesis afforded a series of prenylated derivatives with typical and new xanthone skeletons. Compounds 2, 3, 4 and 9 were reported for the first time to possess a new scaffold of 2H-xanthene- 3,9-dione. Interestingly, analogues 2 and 3 with the new scaffold demonstrated remarkable in vitro growth inhibitory activities against both the cell lines by displaying a greater cytotoxic potency than the standard drugs used in the assay, namely doxorubicin and cisplatin. In contrast, a dramatic loss of activity was observed for the O-prenylated derivatives 9- 11. These findings have highlighted the therapeutic potential of 2H-xanthene-3,9-dione scaffold to be exploitable as drug lead with specific activity against cervical and breast cancers.

  为了研究氧杂蒽酮化合物的抗肿瘤活性，研究人员评估了10种前酰化氧杂蒽酮衍生物2-11及其关键结构单元1,3,6-三羟基氧杂蒽酮1对HeLa和MDA-MB-231癌细胞株的潜在细胞毒性活性。合成过程中得到了一系列具有典型和新型氧杂蒽酮骨架的预炔化衍生物。化合物 2、3、4 和 9 首次被报道具有 2H-氧杂蒽酮-3,9-二酮的新支架。有趣的是，具有新支架的类似物 2 和 3 在体外对两种细胞系都表现出了显著的生长抑制活性，其细胞毒性效力高于试验中使用的标准药物，即多柔比星和顺铂。与此相反，O-异戊烯化衍生物 9-11 的活性急剧下降。这些发现凸显了 2H-氧杂蒽-3,9-二酮支架的治疗潜力，可用作具有特异性宫颈癌和乳腺癌活性的先导药物。
• Design and synthesis of gambogic acid analogs as potent cytotoxic and anti-inflammatory agents
  作者：Chiao-Ting Yen、Kyoko Nakagawa-Goto、Tsong-Long Hwang、Susan L. Morris-Natschke、Kenneth F. Bastow、Yang-Chang Wu、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2012.04.084

  日期：2012.6

  Prenyl-and pyrano-xanthones derived from 1,3,6-trihydroxy-9H-xanthen-9-one, a basic backbone of gambogic acid (GA), were synthesized and evaluated for in vitro cytotoxic effects against four human cancer cell lines (KB, KBvin, A549, and DU-145) and anti-inflammatory activity toward superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, prenylxanthones 7-13 were generally less active than pyranoxanthones 14-21 in both anticancer and anti-inflammatory assays. Furthermore, two angular 3,3-dimethypyranoxanthones (16 and 20) showed the greatest and selective activity against the KBvin multidrug resistant (MDR) cell line with IC50 values of 0.9 and 0.8 mu g/mL, respectively. An angular 3-methyl-3-prenylpyranoxanthone (17) selectively inhibited elastase release with 200 times more potency than phenylmethylsulfonyl fluoride (PMSF), the positive control. (C) 2012 Elsevier Ltd. All rights reserved.
• 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).