(5S)-3-(7-iodohept-6-enyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one | 866885-77-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (5S)-3-(7-iodohept-6-enyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one
• CAS: 866885-77-0
• 化学式: C₁₈H₂₃IO₂S
• 分子量: 430.35
• InChiKey: VMMLHFCOFUQSLW-BUSXIPJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5S)-3-(7-iodohept-6-enyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one 在 bis-triphenylphosphine-palladium(II) chloride 、 Wilkinson's catalyst copper(l) iodide 、 氢气 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.5h， 生成
  参考文献：
  名称：

  Design, syntheses, and biological evaluations of squamostolide and its related analogs

  摘要：

  Squamostolide and its related analogs were designed and synthesized for biological evaluation. All these compounds were tested for growth inhibition activities against human tumor cell lines, in which one of the compounds showed the most potent cyto-toxicity among these derivatives against a full panel of 60 human cancer cell lines. The same compound also showed G2/M phase arrest and a weak apoptotic effect during flow cytometric analysis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.050
• 作为产物：
  描述：

  6-庚炔醇 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (5S)-3-(7-iodohept-6-enyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Design, syntheses, and biological evaluations of squamostolide and its related analogs

  摘要：

  Squamostolide and its related analogs were designed and synthesized for biological evaluation. All these compounds were tested for growth inhibition activities against human tumor cell lines, in which one of the compounds showed the most potent cyto-toxicity among these derivatives against a full panel of 60 human cancer cell lines. The same compound also showed G2/M phase arrest and a weak apoptotic effect during flow cytometric analysis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.050

文献信息

• Synthesis and characterization of photoaffinity probe of acetogenin, a strong inhibitor of mitochondrial complex I
  作者：Shuhei Yamamoto、Masato Abe、Sayo Nakanishi、Masatoshi Murai、Hideto Miyoshi

  DOI：10.1016/j.tetlet.2011.03.149

  日期：2011.6

  Acetogenins are valuable inhibitor probes to get an insight into the structural and functional properties of mitochondrial NADH-ubiquinone oxidoreductase (complex I). We synthesized a photoreactive acetogenin mimic ([I-125]DANA) which retained a strong inhibitory activity. The preliminary photoaffinity labeling with bovine heart submitochondrial particles revealed that [I-125]DANA binds to the ND1 subunit among 45 different subunits with high specificity. (C) 2011 Elsevier Ltd. All rights reserved.