9-hydroxy-8-(3'-(9'-hydroxy-3',3'-dimethyl-7',10'-dioxo-7',10'-dihydro-3'H-naphtho[2,1-b]pyran-8'-yl)-1',4'-dioxo-6'-n-propoxy-1',4'-dihydronaphthalen-2'-yl)-3,3-dimethyl-3H-naphtho[2,1-b]pyran-7,10-dione | 1146942-99-5

• 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'-(9'-hydroxy-3',3'-dimethyl-7',10'-dioxo-7',10'-dihydro-3'H-naphtho[2,1-b]pyran-8'-yl)-1',4'-dioxo-6'-n-propoxy-1',4'-dihydronaphthalen-2'-yl)-3,3-dimethyl-3H-naphtho[2,1-b]pyran-7,10-dione
• 英文别名: 9-Hydroxy-8-[3-(9-hydroxy-3,3-dimethyl-7,10-dioxo-benzo[f]chromen-8-yl)-1,4-dioxo-6-propoxy-2-naphthyl]-3,3-dimethyl-benzo[f]chromene-7,10-dione；9-hydroxy-8-[3-(9-hydroxy-3,3-dimethyl-7,10-dioxobenzo[f]chromen-8-yl)-1,4-dioxo-6-propoxynaphthalen-2-yl]-3,3-dimethylbenzo[f]chromene-7,10-dione
• CAS: 1146942-99-5
• 化学式: C₄₃H₃₂O₁₁
• 分子量: 724.72
• InChiKey: JWUJBFUGUHYSJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  54
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  171
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  9-hydroxy-3,3-dimethyl-3H-naphtho[2,1-b]pyran-7,10-dione 、 2,3-dichloro-6-n-propyloxy-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 8.0h， 以18%的产率得到9-hydroxy-8-(3'-(9'-hydroxy-3',3'-dimethyl-7',10'-dioxo-7',10'-dihydro-3'H-naphtho[2,1-b]pyran-8'-yl)-1',4'-dioxo-6'-n-propoxy-1',4'-dihydronaphthalen-2'-yl)-3,3-dimethyl-3H-naphtho[2,1-b]pyran-7,10-dione
  参考文献：
  名称：

  Antiviral Agents. I. Synthesis and Antiviral Evaluation of Trimeric Naphthoquinone Analogues of Conocurvone

  摘要：

  Conocurvone 是一种从澳大利亚特有灌木 Conosperum sp.（原生植物科）中分离出来的新型天然产物，具有抗艾滋病毒的活性，但它是一种高亲脂性化合物，这表明它的水溶性和生物利用度可能存在问题。本文介绍了一种利用 2-羟基萘醌和 2,3-二卤醌缩合合成三聚萘醌的通用简便方法。报告还介绍了应用这种方法合成一系列更简单、亲油性更低的三聚萘醌简单类似物 conocurvone 及其抗 HIV 活性。

  DOI：

  10.1071/ch08177

文献信息

• Antiviral Agents. I. Synthesis and Antiviral Evaluation of Trimeric Naphthoquinone Analogues of Conocurvone
  作者：Ian T. Crosby、Mark L. Rose、Maree P. Collis、Paula J. de Bruyn、Philip L. C. Keep、Alan D. Robertson

  DOI：10.1071/ch08177

  日期：——

  Conocurvone, a novel natural product isolated from the endemic Australian shrub Conosperum sp. (Proteaceae), exhibits anti-HIV activity but is a highly lipophilic compound, which suggests that there may be problems with its aqueous solubility and bioavailability. A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity.

  Conocurvone 是一种从澳大利亚特有灌木 Conosperum sp.（原生植物科）中分离出来的新型天然产物，具有抗艾滋病毒的活性，但它是一种高亲脂性化合物，这表明它的水溶性和生物利用度可能存在问题。本文介绍了一种利用 2-羟基萘醌和 2,3-二卤醌缩合合成三聚萘醌的通用简便方法。报告还介绍了应用这种方法合成一系列更简单、亲油性更低的三聚萘醌简单类似物 conocurvone 及其抗 HIV 活性。