4-[2,6-Dihydroxy-4-(6,7,8-trihydroxy-2-naphthyl)phenoxy]-3-hydroxy-7-(3,4,5-trihydroxyphenyl)naphthalene-1,2-dione | 1240372-56-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[2,6-Dihydroxy-4-(6,7,8-trihydroxy-2-naphthyl)phenoxy]-3-hydroxy-7-(3,4,5-trihydroxyphenyl)naphthalene-1,2-dione
• 英文别名: 4-[2,6-dihydroxy-4-(6,7,8-trihydroxynaphthalen-2-yl)phenoxy]-3-hydroxy-7-(3,4,5-trihydroxyphenyl)naphthalene-1,2-dione
• CAS: 1240372-56-8
• 化学式: C₃₂H₂₀O₁₂
• 分子量: 596.504
• InChiKey: PTQVGMBSNSFRRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  225
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  7-(3,4,5-trihydroxyphenyl)naphthalene-1,2,3-triol 在 air 作用下， 生成 4-[2,6-Dihydroxy-4-(6,7,8-trihydroxy-2-naphthyl)phenoxy]-3-hydroxy-7-(3,4,5-trihydroxyphenyl)naphthalene-1,2-dione
  参考文献：
  名称：

  New 2-arylnaphthalenediols and triol inhibitors of HIV-1 integrase—Discovery of a new polyhydroxylated antiviral agent

  摘要：

  A series of 13 hydroxylated 2-arylnaphthalenes have been synthesized and evaluated as HIV-1 integrase inhibitors. 7-(3,4,5-Trihydroxyphenyl) naphthalene-1,2,3-triol 1c revealed chemical instability upon storage, leading to the isolation of a dimer 5c which was also tested. In the 2-arylnaphthalene series, all compounds were active against HIV-1 IN with IC50' s within the 1-10 lM range, except for 1c and 5c which displayed submicromolar activity. Antiviral activity against HIV-1 replication was measured on 1b-c and 5c. Amongst the tested molecules, only 5c was found to present antiviral properties with a low cytotoxicity on two different cell lines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.059

文献信息

• New 2-arylnaphthalenediols and triol inhibitors of HIV-1 integrase—Discovery of a new polyhydroxylated antiviral agent
  作者：Cédric Maurin、Cédric Lion、Fabrice Bailly、Nadia Touati、Hervé Vezin、Gladys Mbemba、Jean François Mouscadet、Zeger Debyser、Myriam Witvrouw、Philippe Cotelle

  DOI：10.1016/j.bmc.2010.05.059

  日期：2010.7

  A series of 13 hydroxylated 2-arylnaphthalenes have been synthesized and evaluated as HIV-1 integrase inhibitors. 7-(3,4,5-Trihydroxyphenyl) naphthalene-1,2,3-triol 1c revealed chemical instability upon storage, leading to the isolation of a dimer 5c which was also tested. In the 2-arylnaphthalene series, all compounds were active against HIV-1 IN with IC50' s within the 1-10 lM range, except for 1c and 5c which displayed submicromolar activity. Antiviral activity against HIV-1 replication was measured on 1b-c and 5c. Amongst the tested molecules, only 5c was found to present antiviral properties with a low cytotoxicity on two different cell lines. (C) 2010 Elsevier Ltd. All rights reserved.