3-(4'-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)cyclobut-3-ene-1,2-dione | 1257127-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4'-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)cyclobut-3-ene-1,2-dione
• 英文别名: 3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)cyclobut-3-ene-1,2-dione
• CAS: 1257127-48-2
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: DIYMBFVYTANFSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3,4,5-trimethoxyphenyl)tri-n-butylstannane 、 3-chloro-4-(4-methoxyphenyl)-3-cyclobutene-1,2-dione 在 双(乙腈)氯化钯(II) 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 3-(4'-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Synthesis and antitumor activity of novel 3,4-diaryl squaric acid analogs

  摘要：

  A series of novel 3,4-diaryl squaric acid analogs 4a-r related to combretastatin A-4 (CA4) using squaric acid as the cis-restricted linker were prepared and studied for their anticancer activity against selected human cancer cell lines. New compounds 4g, 4k, 4m, 4n, 4p, 4q and 4r exhibit strong activities against human leukemia cells with IC50 values of <= 20 nM and compounds 4k, 4n, 4p, 4q and 4r showed potent activities against a panel of human tumor cell lines. Compounds 4n and 4p arrest tumor cell cycle in G2-M phase. Computational modeling analysis suggests that the binding mechanism of compound 4n to the colchicine binding site on the microtubules is similar to that of CA4. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.046

文献信息

• Synthesis and antitumor activity of novel 3,4-diaryl squaric acid analogs
  作者：Zong-ying Liu、Yue-ming Wang、Yan-xing Han、Ling Liu、Jie Jin、Hong Yi、Zhuo-rong Li、Jian-dong Jiang、David W. Boykin

  DOI：10.1016/j.ejmech.2013.04.046

  日期：2013.7

  A series of novel 3,4-diaryl squaric acid analogs 4a-r related to combretastatin A-4 (CA4) using squaric acid as the cis-restricted linker were prepared and studied for their anticancer activity against selected human cancer cell lines. New compounds 4g, 4k, 4m, 4n, 4p, 4q and 4r exhibit strong activities against human leukemia cells with IC50 values of <= 20 nM and compounds 4k, 4n, 4p, 4q and 4r showed potent activities against a panel of human tumor cell lines. Compounds 4n and 4p arrest tumor cell cycle in G2-M phase. Computational modeling analysis suggests that the binding mechanism of compound 4n to the colchicine binding site on the microtubules is similar to that of CA4. (C) 2013 Elsevier Masson SAS. All rights reserved.