2-hydroxy-3-(3'-(2''-hydroxy-6'',7''-dimethoxy-1'',4''-dioxodihydronaphthalene-3''-yl)-1',4'-dioxo-6',7'-dimethoxy-naphthalene-2'-yl)-6,7-dimethoxy-1,4-naphthoquinone | 1251860-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-3-(3'-(2''-hydroxy-6'',7''-dimethoxy-1'',4''-dioxodihydronaphthalene-3''-yl)-1',4'-dioxo-6',7'-dimethoxy-naphthalene-2'-yl)-6,7-dimethoxy-1,4-naphthoquinone
• 英文别名: 2,3-Bis(3-hydroxy-6,7-dimethoxy-1,4-dioxo-2-naphthyl)-6,7-dimethoxy-naphthalene-1,4-dione；2,3-bis(3-hydroxy-6,7-dimethoxy-1,4-dioxonaphthalen-2-yl)-6,7-dimethoxynaphthalene-1,4-dione
• CAS: 1251860-74-8
• 化学式: C₃₆H₂₆O₁₄
• 分子量: 682.594
• InChiKey: MSAYOCFUVKIQDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  50
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  198
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  4-hydroxy-6,7-dimethoxynaphthalene-1,2-dione 、 2-bromo-3-(4'-toluenesulfonyloxy)-6,7-dimethoxy-1,4-naphthoquinone 在 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 96.0h， 以4%的产率得到2-hydroxy-3-(3'-(2''-hydroxy-6'',7''-dimethoxy-1'',4''-dioxodihydronaphthalene-3''-yl)-1',4'-dioxo-6',7'-dimethoxy-naphthalene-2'-yl)-6,7-dimethoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Antiviral agents 2. Synthesis of trimeric naphthoquinone analogues of conocurvone and their antiviral evaluation against HIV

  摘要：

  The synthesis of a new series of conocurvone analogues is presented that explores the importance of the pyran rings of conocurvone, their degree of unsaturation as well as the role of alkoxy functionalities as pyran ring replacements, for the inhibition of the HIV-1 integrase (IN) enzyme. Difficulties in synthesising a trimeric naphthoquinone where the central quinone bears a peri-dihydropyran ring was attributed to distortion of the electrophilic dihaloquinone successfully utilised in the past. Increased electron density could also be a factor in reducing reactivity. The desired central dihydropyran bearing trimeric naphthoquinone was successfully synthesised by using a more reactive bromo-tosyloxyquinone intermediate. A maleimide derivative, where the central quinone between the pendant hydroxyquinones was replaced, was successfully synthesised and although it exhibited comparable enzyme inhibitory activity it had negligible HIV inhibitory cellular activity. Compounds were assessed for activity in both in vitro assays using purified recombinant HIV-1 IN and demonstrated superior or comparable activity to conocurvone derivatives previously reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.105

文献信息

• Antiviral agents 2. Synthesis of trimeric naphthoquinone analogues of conocurvone and their antiviral evaluation against HIV
  作者：Ian T. Crosby、David G. Bourke、Eric D. Jones、Paula J. de Bruyn、David Rhodes、Nick Vandegraaff、Susan Cox、Jonathan A.V. Coates、Alan D. Robertson

  DOI：10.1016/j.bmc.2010.06.105

  日期：2010.9

  The synthesis of a new series of conocurvone analogues is presented that explores the importance of the pyran rings of conocurvone, their degree of unsaturation as well as the role of alkoxy functionalities as pyran ring replacements, for the inhibition of the HIV-1 integrase (IN) enzyme. Difficulties in synthesising a trimeric naphthoquinone where the central quinone bears a peri-dihydropyran ring was attributed to distortion of the electrophilic dihaloquinone successfully utilised in the past. Increased electron density could also be a factor in reducing reactivity. The desired central dihydropyran bearing trimeric naphthoquinone was successfully synthesised by using a more reactive bromo-tosyloxyquinone intermediate. A maleimide derivative, where the central quinone between the pendant hydroxyquinones was replaced, was successfully synthesised and although it exhibited comparable enzyme inhibitory activity it had negligible HIV inhibitory cellular activity. Compounds were assessed for activity in both in vitro assays using purified recombinant HIV-1 IN and demonstrated superior or comparable activity to conocurvone derivatives previously reported. (C) 2010 Elsevier Ltd. All rights reserved.