2-(2-Cycloheptylidene-ethyl)-3-hydroxy-[1,4]naphthoquinone | 90149-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-Cycloheptylidene-ethyl)-3-hydroxy-[1,4]naphthoquinone
• CAS: 90149-92-1
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: FDTSYSBUISBRSC-UHFFFAOYSA-N

物化性质

• 沸点：
  466.8±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-Cycloheptylidene-ethyl)-3-hydroxy-[1,4]naphthoquinone 在 硫酸 作用下， 反应 0.25h， 以51%的产率得到Spiro[3,4-dihydrobenzo[h]chromene-2,1'-cycloheptane]-5,6-dione
  参考文献：
  名称：

  .beta.-Lapachone: synthesis of derivatives and activities in tumor models

  摘要：

  In order to find a 3,4-dihydro-2H-naphtho[1,2-b]pyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative [beta-lapachone (10a)], we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring. Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity. Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a. However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as the 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.

  DOI：

  10.1021/jm00374a010
• 作为产物：
  描述：

  2-cycloheptylideneethan-1-ol 在 吡啶 、 氢氧化钾 、 三溴化磷 、 potassium iodide 作用下， 以 乙醚 、 Petroleum ether 为溶剂， 反应 17.0h， 生成 2-(2-Cycloheptylidene-ethyl)-3-hydroxy-[1,4]naphthoquinone
  参考文献：
  名称：

  .beta.-Lapachone: synthesis of derivatives and activities in tumor models

  摘要：

  In order to find a 3,4-dihydro-2H-naphtho[1,2-b]pyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative [beta-lapachone (10a)], we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring. Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity. Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a. However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as the 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.

  DOI：

  10.1021/jm00374a010