3-(3,4-bis(methoxymethoxy)phenyl)-1-(6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one | 1351279-85-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(3,4-bis(methoxymethoxy)phenyl)-1-(6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one
• 英文别名: 3-[3,4-bis(methoxymethoxy)phenyl]-1-[6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
• CAS: 1351279-85-0
• 化学式: C₂₈H₃₆O₁₀
• 分子量: 532.588
• InChiKey: GIRSVCQGTNAZGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  38.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  111.14
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-(3,4-bis(methoxymethoxy)phenyl)-1-(6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one 在 水 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以45%的产率得到3',4',5,7-tetramethoxymethoxy-6-(3,3-dimethylallyl)flavanone
  参考文献：
  名称：

  Pharmacophore identification, virtual screening and biological evaluation of prenylated flavonoids derivatives as PKB/Akt1 inhibitors

  摘要：

  A total of 24 well-defined PKB/Akt1 inhibitors were used to generate pharmacophore models applying Catalyst/HypoGen program. The best ranked model (Hypo_1) was then validated by cost analysis, prediction capability, Cat-Scramble and receiver operating characteristic (ROC) studies. Then, pharmacophore-based virtual screening combined with docking study was performed to search an in-house compound database. Nine preferable hits 75-80, HTS-02143, BTB-14740 and HTS-08006 were prepared and biologically evaluated. Several compounds were identified as good PKB/Akt1 inhibitors, suggesting that Hypo_l would be reliable and useful in virtual screening. Flow cytometric and western blotting analysis on compounds 79 and 80 further demonstrated that the inhibition of phosphorylation of PKB/Akt1 and its substrates (such as GSK beta) was responsible for their cytotoxic activities. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.006
• 作为产物：
  描述：

  3,4-双(甲氧基甲氧基)苯甲醛 、 1-[6-羟基-2,4-二(甲氧基甲氧基)-3-(3-甲基丁-2-烯-1-基)苯基]乙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 36.0h， 以65%的产率得到3-(3,4-bis(methoxymethoxy)phenyl)-1-(6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Pharmacophore identification, virtual screening and biological evaluation of prenylated flavonoids derivatives as PKB/Akt1 inhibitors

  摘要：

  A total of 24 well-defined PKB/Akt1 inhibitors were used to generate pharmacophore models applying Catalyst/HypoGen program. The best ranked model (Hypo_1) was then validated by cost analysis, prediction capability, Cat-Scramble and receiver operating characteristic (ROC) studies. Then, pharmacophore-based virtual screening combined with docking study was performed to search an in-house compound database. Nine preferable hits 75-80, HTS-02143, BTB-14740 and HTS-08006 were prepared and biologically evaluated. Several compounds were identified as good PKB/Akt1 inhibitors, suggesting that Hypo_l would be reliable and useful in virtual screening. Flow cytometric and western blotting analysis on compounds 79 and 80 further demonstrated that the inhibition of phosphorylation of PKB/Akt1 and its substrates (such as GSK beta) was responsible for their cytotoxic activities. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.006