1,3,5,6-tetramethoxy-4-(3-methoxyphenyl)-9H-xanthen-9-one | 1489236-08-9

• 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-4-(3-methoxyphenyl)-9H-xanthen-9-one
• 英文别名: 1,3,5,6-Tetramethoxy-4-(3-methoxyphenyl)xanthen-9-one；1,3,5,6-tetramethoxy-4-(3-methoxyphenyl)xanthen-9-one
• CAS: 1489236-08-9
• 化学式: C₂₄H₂₂O₇
• 分子量: 422.434
• InChiKey: QAMURQSCLKYMOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲酰氯 在 吡啶 、 aluminum (III) chloride 、 四(三苯基膦)钯 、 tetramethylammonium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醚 、 水 为溶剂， 反应 62.17h， 生成 1,3,5,6-tetramethoxy-4-(3-methoxyphenyl)-9H-xanthen-9-one
  参考文献：
  名称：

  Synthesis and biological evaluation of phenyl substituted polyoxygenated xanthone derivatives as anti-hepatoma agents

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.08.020

文献信息

• 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.