8-(3-Chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-9-methoxy-3,3-dimethyl-3H-benzo[f]chromene-7,10-dione | 685552-48-1

• 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: 8-(3-Chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-9-methoxy-3,3-dimethyl-3H-benzo[f]chromene-7,10-dione
• 英文别名: 8-(3-Chloro-1,4-dioxo-2-naphthyl)-9-methoxy-3,3-dimethyl-benzo[f]chromene-7,10-dione；8-(3-chloro-1,4-dioxonaphthalen-2-yl)-9-methoxy-3,3-dimethylbenzo[f]chromene-7,10-dione
• CAS: 685552-48-1
• 化学式: C₂₆H₁₇ClO₆
• 分子量: 460.87
• InChiKey: BTGMEIJRTFFYSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-(3-Chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-9-methoxy-3,3-dimethyl-3H-benzo[f]chromene-7,10-dione 、 2-hydroxy-1,4-naphthoquinone potassium salt 在 18-冠醚-6 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 48.0h， 以14%的产率得到3-hydroxy-3'-(9-methoxy-3,3-dimethyl-7,10dioxo-7,10-dihydro-3H-benzo[f]chromen-8-yl)-2,2'-binaphthalenyl-1,4,1',4'-tetraone
  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：

  2,3-二氯-1,4-萘醌 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 173.0h， 生成 8-(3-Chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-9-methoxy-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

文献信息

• Anti-viral multi-quinone compounds and regiospecific synthesis thereof
  申请人：——

  公开号：US20040087663A1

  公开（公告）日：2004-05-06

  This invention provides various biquinone and trimeric quinone derivatives. The invention also provides a method for synthesis of a multi-quinone compound including reacting a hydroxyquinone anion with a first quinone possessing a first directing group at a C-2 of the first quinone and a second directing group at a C-3 of the first quinone and obtaining a biquinone having one of the first and second directing groups at a C-3 of a first quinone monomer and a hydroxyl group at a C-3′ of a second quinone monomer. The biquinone can be further reacted to obtain various biquinone derivatives or with a second hydroxyquinone anion to obtain trimeric quinone derivatives, including trimeric naphthoquinone derivatives. The biquinones and trimeric quinones of this invention demonstrate antiviral activity and can be used to treat viral infections, particularly HIV infections.

  本发明提供了各种二醌和三聚醌衍生物。本发明还提供了一种合成多醌化合物的方法，包括将羟基醌负离子与具有第一定向基位于第一醌的C-2处和第二定向基位于第一醌的C-3处的第一醌反应，并获得一种二醌，其中第一和第二定向基之一位于第一醌单体的C-3处，而羟基位于第二醌单体的C-3′处。二醌可以进一步反应以获得各种二醌衍生物，或与第二个羟基醌负离子反应以获得三聚醌衍生物，包括三聚萘醌衍生物。本发明的二醌和三聚醌表现出抗病毒活性，可用于治疗病毒感染，特别是HIV感染。
• US6828347B2
  申请人：——

  公开号：US6828347B2

  公开（公告）日：2004-12-07
• Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone
  作者：Kenneth W. Stagliano、Ashkan Emadi、Zhenhai Lu、Helena C. Malinakova、Barry Twenter、Min Yu、Louis E. Holland、Amanda M. Rom、John S. Harwood、Ronak Amin、Allison A. Johnson、Yves Pommier

  DOI：10.1016/j.bmc.2006.04.034

  日期：2006.8

  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.