1-Quinolin-3-yl-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione | 1042149-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-Quinolin-3-yl-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione
• CAS: 1042149-73-4
• 化学式: C₂₀H₁₇NO₅
• 分子量: 351.359
• InChiKey: KQEYYCPCFSFEDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 二甲基亚砜 、 palladium(II) iodide 作用下， 反应 94.0h， 以93%的产率得到1-Quinolin-3-yl-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione
  参考文献：
  名称：

  Synthesis and antitumor activity of benzils related to combretastatin A-4

  摘要：

  A series of benzil derivatives related to combretastatin A-4 (CA-4) have been synthesized by oxidation of diarylalkynes promoted by PdI2 in DMSO. Using this new protocol, 14 benzils were prepared in good to excellent yields and their biological activity has been delineated. Several benzils exhibited excellent antiproliferative activity: for example, 4j and 4k bearing the greatest resemblance to CA-4 and AVE-8062, respectively, were found to inhibit cell growth at the nanomolar level (20-50 nM) on four human tumor cell lines. Flow cytometric analysis indicates that these compounds act as antimitotics and arrest the cell cycle in G(2)/M phase. A cell-based assay indicated that compounds 4j and 4k displayed a similar inhibition of tubulin assembly with an IC50 value similar to CA-4. These results clearly demonstrated that the Z-double bond of CA-4 can be replaced by a 1,2-diketone unit without significant loss of cytotoxicity and inhibition of tubulin assembly potency. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.053