(E)-methyl 4-((3-methoxy-3-oxoprop-1-en-1-yl)oxy)non-2-ynoate | 1455506-59-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-methyl 4-((3-methoxy-3-oxoprop-1-en-1-yl)oxy)non-2-ynoate
• 英文别名: methyl (4R)-4-[(E)-3-methoxy-3-oxoprop-1-enoxy]non-2-ynoate
• CAS: 1455506-59-8
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: LPEWIYOOYMXULY-HCRIHEDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (R)-(+)-1-辛炔-3-醇 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 (E)-methyl 4-((3-methoxy-3-oxoprop-1-en-1-yl)oxy)non-2-ynoate
  参考文献：
  名称：

  Molecular docking studies of the interaction between propargylic enol ethers and human DNA topoisomerase IIα

  摘要：

  Having identified a novel human DNA topoisomerase II alpha (TOP2) catalytic inhibitor from a small and structure-focused library of propargylic enol ethers, we decided to analyze if the chirality of these compounds plays a determinant role in their antiproliferative activity. In this study, we describe for the first time the synthesis of the corresponding enantiomers and the biological evaluation against a panel of representative human solid tumor cell lines. Experimental results show that chirality does not influence the reported antiproliferative activity of these compounds. Docking studies of corresponding enantiomers against TOP2 reinforce the finding that the biological effect is not chiral-dependent and that these family of compounds seem to act as TOP2 catalytic inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.055

文献信息

• Molecular docking studies of the interaction between propargylic enol ethers and human DNA topoisomerase IIα
  作者：Gastón Silveira-Dorta、Inês J. Sousa、Carla Ríos-Luci、Víctor S. Martín、Miguel X. Fernandes、José M. Padrón

  DOI：10.1016/j.bmcl.2013.07.055

  日期：2013.10

  Having identified a novel human DNA topoisomerase II alpha (TOP2) catalytic inhibitor from a small and structure-focused library of propargylic enol ethers, we decided to analyze if the chirality of these compounds plays a determinant role in their antiproliferative activity. In this study, we describe for the first time the synthesis of the corresponding enantiomers and the biological evaluation against a panel of representative human solid tumor cell lines. Experimental results show that chirality does not influence the reported antiproliferative activity of these compounds. Docking studies of corresponding enantiomers against TOP2 reinforce the finding that the biological effect is not chiral-dependent and that these family of compounds seem to act as TOP2 catalytic inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.