6-Methyl-5-(3-methylbut-2-enyl)-5,8-dihydronaphthalene-1,4-diol | 1529815-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-Methyl-5-(3-methylbut-2-enyl)-5,8-dihydronaphthalene-1,4-diol
• 英文别名: 6-methyl-5-(3-methylbut-2-enyl)-5,8-dihydronaphthalene-1,4-diol
• CAS: 1529815-53-9
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: DNRTVBBBBIIOHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  罗勒烯 、 2,5-二羟基苯甲酸 在 碘苯二乙酸 作用下， 以 异丙醚 、 乙腈 为溶剂， 反应 1.0h， 以64.28%的产率得到6-Methyl-5-(3-methylbut-2-enyl)-5,8-dihydronaphthalene-1,4-diol
  参考文献：
  名称：

  Synthesis, anti-HIV activity, integrase enzyme inhibition and molecular modeling of catechol, hydroquinone and quinol labdane analogs

  摘要：

  Labdane analogs with o-quinol, catechol and hydroquinone moiety have been synthesized using Diels-Alder reaction of methyl 3,4-dioxocyclohexa-1,5-diene-carboxylate, 3,4-dioxocyclohexa-1,5-dienecarboxylic acid and 3,6-dioxocyclohexa-1,4-dienecarboxylic acid with mono terpene 1,3-dienes, namely ocimene and myrcene. The resulting molecules and their derivatives were evaluated for their anti-HIV-1 activity using TZM-bl cell based virus infectivity assay. Two molecules 13 and 18 showed anti-HIV activity with IC50 values 5.0 (TI = 11) and 4.6 (TI = 46) mu M, respectively. The compounds 17, 18 and 20 showed efficacy against HIV-1 integrase activity and showed inhibition with IC50 13.4, 11.1 and 11.5 mu M, respectively. The HIV-1 integrase inhibition activity of these synthetic molecules was comparable with integric acid, the natural fungal metabolite. Molecular modeling studies for the HIV-1 integrase inhibition of these active synthetic molecules indicated the binding to the active site residues of the enzyme. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.014