(E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-1-(isothiocyanatomethyl)-3-methylquinolin-4(1H)-one | 1430330-15-6

• 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: (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-1-(isothiocyanatomethyl)-3-methylquinolin-4(1H)-one
• 英文别名: 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-1-(isothiocyanatomethyl)-3-methylquinolin-4-one
• CAS: 1430330-15-6
• 化学式: C₂₂H₂₆N₂OS
• 分子量: 366.527
• InChiKey: SRCHPGDOPKXPHK-SFQUDFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-1-(isothiocyanatomethyl)-3-methylquinolin-4(1H)-one 、 碘甲烷 、 sodium thiomethoxide 以 乙腈 为溶剂， 反应 0.83h， 以43%的产率得到intervenolin
  参考文献：
  名称：

  Synthesis of Intervenolin, an Antitumor Natural Quinolone with Unusual Substituents

  摘要：

  Synthesis of intervenolin, a natural quinolone discovered by screening for selective growth inhibitors of cancer cells cocultured with stromal cells over monocultured cells, was achieved. The synthesis utilized a thiocyanate-isothiocyanate rearrangement and Suzuki-Miyaura coupling to furnish the characteristic substituents, the iminodithiocarbonate moiety, and the geranyl side chain, respectively. In vivo studies showed that intervenolin inhibited tumor tissue growth in model mice.

  DOI：

  10.1021/ol400587a
• 作为产物：
  描述：

  4-羟基-3-甲基-2(1h)-喹啉酮 在 咪唑 、 2,6-二甲基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 水 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.83h， 生成 (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-1-(isothiocyanatomethyl)-3-methylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis of Intervenolin, an Antitumor Natural Quinolone with Unusual Substituents

  摘要：

  Synthesis of intervenolin, a natural quinolone discovered by screening for selective growth inhibitors of cancer cells cocultured with stromal cells over monocultured cells, was achieved. The synthesis utilized a thiocyanate-isothiocyanate rearrangement and Suzuki-Miyaura coupling to furnish the characteristic substituents, the iminodithiocarbonate moiety, and the geranyl side chain, respectively. In vivo studies showed that intervenolin inhibited tumor tissue growth in model mice.

  DOI：

  10.1021/ol400587a

文献信息

• Synthesis of Intervenolin, an Antitumor Natural Quinolone with Unusual Substituents
  作者：Hikaru Abe、Manabu Kawada、Hiroyuki Inoue、Shun-ichi Ohba、Akio Nomoto、Takumi Watanabe、Masakatsu Shibasaki

  DOI：10.1021/ol400587a

  日期：2013.5.3

  Synthesis of intervenolin, a natural quinolone discovered by screening for selective growth inhibitors of cancer cells cocultured with stromal cells over monocultured cells, was achieved. The synthesis utilized a thiocyanate-isothiocyanate rearrangement and Suzuki-Miyaura coupling to furnish the characteristic substituents, the iminodithiocarbonate moiety, and the geranyl side chain, respectively. In vivo studies showed that intervenolin inhibited tumor tissue growth in model mice.