4-hydroxy-3-(2-methylbut-3-yn-2-yloxy)-9H-xanthen-9-one | 1383484-83-0

• 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: 4-hydroxy-3-(2-methylbut-3-yn-2-yloxy)-9H-xanthen-9-one
• 英文别名: 4-hydroxy-3-((2-methylbut-3-yn-2-yl)oxy)xanthone；4-Hydroxy-3-(2-methylbut-3-yn-2-yloxy)xanthen-9-one；4-hydroxy-3-(2-methylbut-3-yn-2-yloxy)xanthen-9-one
• CAS: 1383484-83-0
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: ZYPXCEZEYFLBJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(2-methylbut-3-yn-2-yloxy)-9H-xanthen-9-one 在 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 0.33h， 以87%的产率得到4-hydroxy-3-(2-methylbut-3-en-2-yloxy)-9H-xanthen-9-one
  参考文献：
  名称：

  Garcinia Xanthones as Orally Active Antitumor Agents

  摘要：

  Using a newly developed strategy whose key step is the regioselective propargylation of hydroxyxanthone substrates, 99 structurally diverse Garcinia natural-product-like xanthones based on gambogic acid were designed and synthesized and their in vitro antitumor activity was evaluated. A set of 40 related compounds was chosen for determination of their physicochemical properties including polar surface area, log D-7.4, aqueous solubility, and permeability at pH 7.4. In the light of the in vitro antitumor activity and the physicochemical properties, two compounds were advanced into in vivo efficacy experiments. The antitumor activity of compound 112, administered po, showed more potent in vivo oral antitumor activity than gambogic acid.

  DOI：

  10.1021/jm301593r
• 作为产物：
  描述：

  3,4-dimethoxyxanthen-9-one 在 aluminum (III) chloride 、 copper(l) iodide 、 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 4.0h， 生成 3,3-dimethyl-2-methylene-2H-[1,4]dioxino[2,3-c]xanthen-7(3H)-one 、 4-hydroxy-3-(2-methylbut-3-yn-2-yloxy)-9H-xanthen-9-one
  参考文献：
  名称：

  Pyranoxanthones: Synthesis, growth inhibitory activity on human tumor cell lines and determination of their lipophilicity in two membrane models

  摘要：

  The benzopyran and dihydrobenzopyran moieties can be considered as "privileged motifs" in drug discovery being good platforms for the search of new bioactive compounds. These moieties are commonly found fused to the xanthonic scaffold belonging to the biologically important family of the generally designated prenylated xanthones. Several pyranoxanthones have shown promising antitumor activity and since most of them are from natural origin, the biosynthetic pathway only allows a particular pattern of substitution which limits their structural diversity and renders any broad structure activity study hard to be established. Accordingly, with the aim of rationalizing the importance of the fused ring orientation and oxygenation pattern in pyranoxanthones, this study describes the synthesis of 14 new pyranoxanthones and evaluation of their cell growth inhibitory activity in four human tumor cell lines as well as their lipophilicity in two membrane models. This systematic approach allowed establishing structure activity and structure lipophilicity relationships for the obtained compounds in combination with 6 previously described compounds. From this work an angular pyranoxanthone scaffold emerged as particularly promising, presenting a potent cell growth inhibitory activity and suitable drug-like lipophilicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.012

文献信息

• Pyranoxanthones: Synthesis, growth inhibitory activity on human tumor cell lines and determination of their lipophilicity in two membrane models
  作者：Carlos M.G. Azevedo、Carlos M.M. Afonso、José X. Soares、Salette Reis、Diana Sousa、Raquel T. Lima、M. Helena Vasconcelos、Madalena Pedro、João Barbosa、Luís Gales、Madalena M.M. Pinto

  DOI：10.1016/j.ejmech.2013.09.012

  日期：2013.11

  The benzopyran and dihydrobenzopyran moieties can be considered as "privileged motifs" in drug discovery being good platforms for the search of new bioactive compounds. These moieties are commonly found fused to the xanthonic scaffold belonging to the biologically important family of the generally designated prenylated xanthones. Several pyranoxanthones have shown promising antitumor activity and since most of them are from natural origin, the biosynthetic pathway only allows a particular pattern of substitution which limits their structural diversity and renders any broad structure activity study hard to be established. Accordingly, with the aim of rationalizing the importance of the fused ring orientation and oxygenation pattern in pyranoxanthones, this study describes the synthesis of 14 new pyranoxanthones and evaluation of their cell growth inhibitory activity in four human tumor cell lines as well as their lipophilicity in two membrane models. This systematic approach allowed establishing structure activity and structure lipophilicity relationships for the obtained compounds in combination with 6 previously described compounds. From this work an angular pyranoxanthone scaffold emerged as particularly promising, presenting a potent cell growth inhibitory activity and suitable drug-like lipophilicity. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Garcinia Xanthones as Orally Active Antitumor Agents
  作者：Xiaojin Zhang、Xiang Li、Haopeng Sun、Xiaojian Wang、Li Zhao、Yuan Gao、Xiaorong Liu、Shenglie Zhang、Yanyan Wang、Yingrui Yang、Su Zeng、Qinglong Guo、Qidong You

  DOI：10.1021/jm301593r

  日期：2013.1.10

  Using a newly developed strategy whose key step is the regioselective propargylation of hydroxyxanthone substrates, 99 structurally diverse Garcinia natural-product-like xanthones based on gambogic acid were designed and synthesized and their in vitro antitumor activity was evaluated. A set of 40 related compounds was chosen for determination of their physicochemical properties including polar surface area, log D-7.4, aqueous solubility, and permeability at pH 7.4. In the light of the in vitro antitumor activity and the physicochemical properties, two compounds were advanced into in vivo efficacy experiments. The antitumor activity of compound 112, administered po, showed more potent in vivo oral antitumor activity than gambogic acid.