3-benzyl-5-fluoro-1-((1,6,8-trimethoxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidine-2,4(1H,3H)-dione | 1354568-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-benzyl-5-fluoro-1-((1,6,8-trimethoxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 3-Benzyl-5-fluoro-1-[(1,6,8-trimethoxy-3-methyl-9,10-dioxoanthracen-2-yl)methyl]pyrimidine-2,4-dione
• CAS: 1354568-76-5
• 化学式: C₃₀H₂₅FN₂O₇
• 分子量: 544.536
• InChiKey: SFROBPJJYPNKJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  大黄素 在 氯化亚砜 、 sodium dithionite 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 28.0h， 生成 3-benzyl-5-fluoro-1-((1,6,8-trimethoxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and antitumor activity of conjugates of 5-Fluorouracil and emodin

  摘要：

  A series of conjugates of 5-Fluorouracil (5-FU) and emodin were synthesized by coupling trimethyl emodin with N-1, N-3 dialkylated 5-FU. The 5-FU moiety contained various substituents at the N-3-position were linked to the 2-position of trimethyl emodin via a methylene linkage. Their cytotoxicity against three cancer cell lines and one noncancerous cell were studied. The results revealed that some of conjugates exhibited better or comparable in vitro antitumor activity to 5-FU and emodin and low toxicity in the normal cell. The structure activity relationship study showed N-3-aromatic substituent was important for their cytotoxic activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.050

文献信息

• Synthesis and antitumor activity of conjugates of 5-Fluorouracil and emodin
  作者：Li-Ming Zhao、Li-Ming Zhang、Jin-Juan Liu、Li-Jing Wan、Yong-Qiang Chen、Shu-Qing Zhang、Zhi-Wei Yan、Ji-Hong Jiang

  DOI：10.1016/j.ejmech.2011.10.050

  日期：2012.1

  A series of conjugates of 5-Fluorouracil (5-FU) and emodin were synthesized by coupling trimethyl emodin with N-1, N-3 dialkylated 5-FU. The 5-FU moiety contained various substituents at the N-3-position were linked to the 2-position of trimethyl emodin via a methylene linkage. Their cytotoxicity against three cancer cell lines and one noncancerous cell were studied. The results revealed that some of conjugates exhibited better or comparable in vitro antitumor activity to 5-FU and emodin and low toxicity in the normal cell. The structure activity relationship study showed N-3-aromatic substituent was important for their cytotoxic activity. (C) 2011 Elsevier Masson SAS. All rights reserved.