2-iodo-3-[(trifluoromethanesulfonyl)oxy]-1,4-naphthoquinone | 908128-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-iodo-3-[(trifluoromethanesulfonyl)oxy]-1,4-naphthoquinone
• 英文别名: (3-Iodo-1,4-dioxonaphthalen-2-yl) trifluoromethanesulfonate
• CAS: 908128-28-9
• 化学式: C₁₁H₄F₃IO₅S
• 分子量: 432.115
• InChiKey: KBJLXGSXBQJIRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-iodo-3-[(trifluoromethanesulfonyl)oxy]-1,4-naphthoquinone 在 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 171.0h， 生成 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：

  三氟甲磺酸酐 、 2-hydroxy-3-iodo-1,4-naphthoquinone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以77%的产率得到2-iodo-3-[(trifluoromethanesulfonyl)oxy]-1,4-naphthoquinone
  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