9-Hydroxy-8-(3-iodo-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3,3-dimethyl-3H-benzo[f]chromene-7,10-dione | 908128-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 9-Hydroxy-8-(3-iodo-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3,3-dimethyl-3H-benzo[f]chromene-7,10-dione
• CAS: 908128-13-2
• 化学式: C₂₅H₁₅IO₆
• 分子量: 538.295
• InChiKey: USBVLRNIRJCCKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  32.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  97.74
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  9-Hydroxy-8-(3-iodo-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3,3-dimethyl-3H-benzo[f]chromene-7,10-dione 、 trimethoxonium tetrafluoroborate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以93%的产率得到8-(3-Iodo-1,4-dioxo-2-naphthyl)-9-methoxy-3,3-dimethyl-benzo[f]chromene-7,10-dione
  参考文献：
  名称：

  Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone

  摘要：

  Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.04.034
• 作为产物：
  描述：

  2-hydroxy-3-iodo-1,4-naphthoquinone 在 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 168.5h， 生成 9-Hydroxy-8-(3-iodo-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3,3-dimethyl-3H-benzo[f]chromene-7,10-dione
  参考文献：
  名称：

  Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone

  摘要：

  Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.04.034