(E)-4-(3-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-oxoprop-1-en-1-yl)-N-(thiophen-2-ylmethyl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (E)-4-(3-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-oxoprop-1-en-1-yl)-N-(thiophen-2-ylmethyl)benzamide
• 英文别名: 4-[(E)-3-(9,10-dioxoanthracen-1-yl)-3-oxoprop-1-enyl]-N-(thiophen-2-ylmethyl)benzamide
• 化学式: C₂₉H₁₉NO₄S
• 分子量: 477.54
• InChiKey: ZGFJWXBDCBGHLA-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(蒽-1-基)乙酮 在 chromium(VI) oxide 、 氯化亚砜 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 10.08h， 生成 (E)-4-(3-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-oxoprop-1-en-1-yl)-N-(thiophen-2-ylmethyl)benzamide
  参考文献：
  名称：

  Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents

  摘要：

  A series of 23 novel anthraquinone-chalcone hybrids containing amide function was synthesized and structurally characterized. Sixteen compounds exerted strong cytotoxic activities against K562, Jurkat and HL-60 leukemia cell lines and significantly lower cytotoxic effects against normal MRC-5 cells, indicating very high selectivity in their anticancer action. The compounds 6g, 6u and 6v activate apoptosis in K562 cells through the extrinsic and intrinsic apoptotic pathway. The compound 6e triggered apoptosis in K562 cells only through the extrinsic apoptotic pathway. Treatment of K562 cells with each of these four compounds caused decrease in the expression levels of MMP2, MMP9, and VEGF, suggesting their anti-invasive, antimetastatic and antiangiogenic properties. The compounds 6g and 6v downregulated expression levels of miR-155 in K562 cells, while compounds 6e and 6u upregulated miR-155 levels in treated cells, in comparison with control cells. The structurebased 3-D QSAR models for 6f, 6e, 6i and 61 describe pro-apoptotic activity against caspase-3.

  DOI：

  10.1016/j.bmcl.2018.06.048

文献信息

• Highly selective anthraquinone-chalcone hybrids as potential antileukemia agents
  作者：Tatjana Stanojković、Violeta Marković、Ivana Z. Matić、Milan P. Mladenović、Nina Petrović、Ana Krivokuća、Miloš Petković、Milan D. Joksović

  DOI：10.1016/j.bmcl.2018.06.048

  日期：2018.8

  A series of 23 novel anthraquinone-chalcone hybrids containing amide function was synthesized and structurally characterized. Sixteen compounds exerted strong cytotoxic activities against K562, Jurkat and HL-60 leukemia cell lines and significantly lower cytotoxic effects against normal MRC-5 cells, indicating very high selectivity in their anticancer action. The compounds 6g, 6u and 6v activate apoptosis in K562 cells through the extrinsic and intrinsic apoptotic pathway. The compound 6e triggered apoptosis in K562 cells only through the extrinsic apoptotic pathway. Treatment of K562 cells with each of these four compounds caused decrease in the expression levels of MMP2, MMP9, and VEGF, suggesting their anti-invasive, antimetastatic and antiangiogenic properties. The compounds 6g and 6v downregulated expression levels of miR-155 in K562 cells, while compounds 6e and 6u upregulated miR-155 levels in treated cells, in comparison with control cells. The structurebased 3-D QSAR models for 6f, 6e, 6i and 61 describe pro-apoptotic activity against caspase-3.