(hexacarbonyldicobalt)-2-methyl-3-butyn-2-yl para-nitrophenyl ether | 1417919-60-8

• 英文名称: (hexacarbonyldicobalt)-2-methyl-3-butyn-2-yl para-nitrophenyl ether
• CAS: 1417919-60-8
• 化学式: C₁₇H₁₁Co₂NO₉
• 分子量: 491.262
• InChiKey: VSBOLUDHADUYNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  对氟硝基苯 、 2-甲基-3-丁炔-2-醇 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 生成 (hexacarbonyldicobalt)-2-methyl-3-butyn-2-yl para-nitrophenyl ether
  参考文献：
  名称：

  Anticancer (hexacarbonyldicobalt)propargyl aryl ethers: Synthesis, antiproliferative activity, apoptosis induction, and effect on cellular oxidative stress

  摘要：

  While an increasing number of (hexacarbonyldicobalt)alkynes have been found to possess antiproliferative activity against a number of cancer cell lines, the role of the organometallic moiety in this bioactivity is not well understood. To gain a better understanding of cobalt's role in the medicinal chemistry of these compounds, several simplified analogs of a known organocobalt anticancer compound were synthesized and assessed for antiproliferative activity against MDA-MB-231 human breast cancer cells. These compounds, mostly (hexacarbonyldicobalt)propargyl aryl ethers, caused 45-93% growth inhibition of that cell line at 40 mu M in a 72 h crystal violet staining assay. The most active analog was the organocobalt nitroaromatic ether 3a, with an IC50 of 3.3 +/- 0.9 mu M. Flow cytometric assays on the same cell line demonstrated that 3a strongly induces apoptosis, arrests the cell cycle at the S phase, increases cellular oxidative stress levels, and induces permeability of the mitochondria! membrane. While the non-cobalt-containing precursor to 3a also caused an increase in mitochondrial membrane permeability, it did not produce an increase in oxidative stress levels, nor did it have apoptosis-inducing or antiproliferative effects. The induction of oxidative stress in the cell may be responsible for some of the antiproliferative activity of compound 3a against this cell line. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2012.10.014