1,3,5,6-tetramethoxy xanthone | 3660-86-4

• 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: 1,3,5,6-tetramethoxy xanthone
• 英文别名: 1,3,5,6-tetramethyoxyxanthone；1,3,5,6-tetramethoxyxanthone；1,3,5,6-tetramethoxy-xanthen-9-one；1,3,5,6-Tetramethoxy-xanthen-9-on；1,3,5,6-Tetramethoxy-xanthon；1,3,5,6-Tetramethoxyxanthon；Xanthen-9-one, 1,3,5,6-tetramethoxy-；1,3,5,6-tetramethoxyxanthen-9-one
• CAS: 3660-86-4
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: BKKSNWYHPJPCQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,5,6-tetramethoxy xanthone 在 吡啶 、 氢碘酸 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 生成 1,3,5,6-tetrahydroxyxanthone tetraacetate
  参考文献：
  名称：

  γ-吡喃酮化合物。II：四氧合氧杂蒽酮的合成和抗血小板作用

  摘要：

  甲硫酚及其类似物1,3,5,6-，3,4,5,6-，3,4,6,7-和2,3,6,7-四羟基黄酮是由二苯甲酮前体通过Friedel-进行酰化反应，然后进行碱催化的环化反应以消除甲醇。3,4,6,7-和2,3,6,7-四羟基黄酮四乙酸盐对花生四烯酸诱导的血小板聚集均显示出有效的抗血小板聚集作用。3,4,6,7-四羟基黄酮四乙酸盐和1,3,5,6-四羟基黄酮对胶原蛋白诱导的血小板聚集表现出有效且显着的抗血小板聚集作用。

  DOI：

  10.1002/jps.2600811114
• 作为产物：
  描述：

  1,3,5,6-tetrahydroxyxanthone tetraacetate 在 硫酸 、 potassium carbonate 、 丙酮 作用下， 生成 1,3,5,6-tetramethoxy xanthone
  参考文献：
  名称：

  King et al., Journal of the Chemical Society, 1953, p. 3932,3935

  摘要：

  DOI：

文献信息

• Leiaxanthone, A 1,3,5,6-tetraoxygenated xanthone from Haploclathra leiantha
  作者：Tanus J. Nagem、José C. Da Silveira

  DOI：10.1016/s0031-9422(00)85510-7

  日期：1986.1

  Abstract A new xanthone was isolated from the trunk wood of Haploclatha leiantha and its structure determined by UV, IR and mass spectrometry as 1,3-dihydroxy-5,6-dimethoxyxanthone.

  摘要 从Haploclatha leiantha 树干木材中分离得到一种新的呫吨酮，并通过紫外、红外和质谱法确定其结构为1,3-二羟基-5,6-二甲氧基呫吨酮。
• Ferrxanthone, a 1,3,5,6-tetraoxygenated xanthone from Mesua ferrea
  作者：Suresh Walia、S.K. Mukerjee

  DOI：10.1016/s0031-9422(00)83507-4

  日期：1984.1

  Abstract A new xanthone was isolated from the heartwood of Mesua ferrea and its structure determined by UV, IR, NMR and mass spectrometry as 1,3-dimethoxy-5,6-dihydroxyxanthone.

  摘要 从Mesua ferrea 的心材中分离得到一种新的呫吨酮，其结构经紫外、红外、核磁共振和质谱鉴定为1,3-二甲氧基-5,6-二羟基呫吨酮。
• Synthesis and biological evaluation of phenyl substituted polyoxygenated xanthone derivatives as anti-hepatoma agents
  作者：Ming Dai、Xing Yuan、Jian Kang、Zhi-Jun Zhu、Rong-Cai Yue、Hu Yuan、Bing-Yang Chen、Wei-Dong Zhang、Run-Hui Liu、Qing-Yan Sun

  DOI：10.1016/j.ejmech.2013.08.020

  日期：2013.11

  A series of novel derivatives of phenyl substituted tetramethoxy xanthone were synthesized and evaluated for their in vitro cytotoxicity against human hepatocellular carcinoma (HCC) and non-tumor hepatic cells. Among these derivatives, compound 6 was more potent than positive control 5-fluorouracil (5-Fu) on QGY-7703 and SMMC-7721 cells with IC50 values of 6.27 mu M, 7.50 mu M and 15.56 mu M, 14.55 mu M respectively. Furthermore, compounds 6, 14, 16, and 29 exhibited much better selectivity toward the normal hepatic cell line QSG-7701 than 5-Fu. Additionally, compound 6 significantly induced cell apoptosis in QGY-7703 cells. Our findings suggested that these phenylxanthone derivatives may hold promise as chemotherapeutic agents for the treatment of human HCC. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Relationship between protective effect of xanthone on endothelial cells and endogenous nitric oxide synthase inhibitors
  作者：De-Jian Jiang、Gao-Yun Hu、Jun-Lin Jiang、Hong-Lin Xiang、Han-Wu Deng、Yuan-Jian Li

  DOI：10.1016/j.bmc.2003.08.015

  日期：2003.11

  1, 3,5,6-tetrahydroxyxanthone was synthesized. The relationship between protective effect of xanthone on endothelial cells and endogenous nitric oxide synthase inhibitors was investigated. Endothelial cells were treated with ox-LDL (100 mug/mL) for 48 h. Adhesion of monocytes to endothelial cells and release of lactate dehydrogenase (LDH) was determined. Levels of tumor necrosis factor-alpha (TNF-alpha), monocyte chemoattractant protein-1 (MCP-1), nitric oxide (NO) and asymmetric dimethylarginine (ADMA, an endogenous inhibitor of nitric oxide synthase) in conditioned medium and activity of dimethylarginine dimethylaminohydrolase (DDAH) in endothelial cells were measured. Incubation of endothelial cells with ox-LDL (100 mug/mL) for 48 It markedly enhanced the adhesion of monocytes to endothelial cells, increased the release of LDH, the levels of TNF-alpha, MCP-1 and ADMA, and decreased the content of NO and the activity of DDAH. Xanthone (1,3,5,6-tetrahydroxyxanthone) (1, 3 or 10 mumol/L) significantly inhibited the increased adhesion of monocytes to endothelial cells and attenuated the increased levels of LDH, MCPA and ADMA induced by ox-LDL. Xanthone (1,3,5,6-tetrahydroxyxanthone) (3 or 10 mumol/L) significantly attenuated the increased level of TNF-a and decreased level of NO and activity of DDAH by ox-LDL. The present results suggest that xanthone (1,3,5,6-tetrahydroxyxanthone) preserves endothelial cells and inhibits the increased adhesion of monocytes to endothelial cells induced by ox-LDL, and that the protective effect of xanthone (1,3,5,6-tetrahydroxyxanthone) on endothelial cells is related to reduction of ADMA concentration via increase of DDAH activity. (C) 2003 Elsevier Ltd. All rights reserved.