4-diethanolaminomethyl-8,10-dihydroxy-1,9-bis(3-methylbut-2-en-yl)-3,3a,4,5-tetrahydro-1,5-methano-1H,7H-furo[3,4-d]xanthene-7,13-dione | 1383484-49-8

• 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-diethanolaminomethyl-8,10-dihydroxy-1,9-bis(3-methylbut-2-en-yl)-3,3a,4,5-tetrahydro-1,5-methano-1H,7H-furo[3,4-d]xanthene-7,13-dione
• 英文别名: 18-[[Bis(2-hydroxyethyl)amino]methyl]-6,8-dihydroxy-7,15-bis(3-methylbut-2-enyl)-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4(9),5,7,11-tetraene-10,14-dione
• CAS: 1383484-49-8
• 化学式: C₃₁H₃₉NO₈
• 分子量: 553.653
• InChiKey: UPCIGEOMOBPQFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,5-dihydroxy-3,6-bis(2-methylbut-3-yn-2-yloxy)-9H-xanthen-9-one 在 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 25.0~120.0 ℃ 、101.33 kPa 条件下， 反应 7.67h， 生成 4-diethanolaminomethyl-8,10-dihydroxy-1,9-bis(3-methylbut-2-en-yl)-3,3a,4,5-tetrahydro-1,5-methano-1H,7H-furo[3,4-d]xanthene-7,13-dione 、 4-diethanolaminomethyl-8,10-dihydroxy-1,11-bis(3-methylbut-2-en-yl)-3,3a,4,5-tetrahydro-1,5-methano-1H,7H-furo[3,4-d]xanthene-7,13-dione
  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

文献信息

• 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.