Methyl 8-hydroxy-3-methyl-4-(3-methylbut-2-enyl)-7-oxo-1,4-dihydronaphthalene-4a-carboxylate | 1529815-47-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Methyl 8-hydroxy-3-methyl-4-(3-methylbut-2-enyl)-7-oxo-1,4-dihydronaphthalene-4a-carboxylate
• 英文别名: methyl 8-hydroxy-3-methyl-4-(3-methylbut-2-enyl)-7-oxo-1,4-dihydronaphthalene-4a-carboxylate
• CAS: 1529815-47-1
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: PTVBOWUZKWSBCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 8-hydroxy-3-methyl-4-(3-methylbut-2-enyl)-7-oxo-1,4-dihydronaphthalene-4a-carboxylate 、 乙酸酐 在 吡啶 作用下， 反应 18.0h， 以65.9%的产率得到Methyl 8-acetoxy-3-methyl-4-(3-methylbut-2-enyl)-7-oxo-1,4-dihydronaphthalene-4a-carboxylate
  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
• 作为产物：
  描述：

  3,4-二羟基苯甲酸甲酯 、 罗勒烯 在 silver(l) oxide 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 23.0h， 以80.5%的产率得到Methyl 8-hydroxy-3-methyl-4-(3-methylbut-2-enyl)-7-oxo-1,4-dihydronaphthalene-4a-carboxylate
  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

文献信息

• Synthesis, anti-HIV activity, integrase enzyme inhibition and molecular modeling of catechol, hydroquinone and quinol labdane analogs
  作者：Rohan Pawar、Tiyasa Das、Sanjay Mishra、Nutan、Boskey Pancholi、Satish K. Gupta、Sujata V. Bhat

  DOI：10.1016/j.bmcl.2013.11.014

  日期：2014.1

  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.