3-(2,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-4-(methoxymethoxy)-5-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one | 1186018-78-9

• 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-(2,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-4-(methoxymethoxy)-5-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one
• 英文别名: 2-hydroxy-2',4,4'-tri(methoxymethoxy)-5-(3,3-dimethylallyl)chalcone
• CAS: 1186018-78-9
• 化学式: C₂₆H₃₂O₈
• 分子量: 472.535
• InChiKey: OWUHROFJNWHCHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  34.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(2,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-4-(methoxymethoxy)-5-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one 在 吡啶 、 水 、 碘 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成
  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：

  苯(甲)醛,2,4-二(甲氧基甲氧基)- 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 57.0h， 生成 3-(2,4-bis(methoxymethoxy)phenyl)-1-(2-hydroxy-4-(methoxymethoxy)-5-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Kuwanons I和J和Brosimones A和B的对映仿生全合成。

  摘要：

  异戊二烯类黄酮Diels-Alder天然产物（-）-kuwanon I，（+）-kuwanon J，（-）-溴亚砜A和（-）-溴亚砜B的首个对映选择性全合成是基于一种基于简洁的综合策略。合成的关键元素包括由手性配体/硼路易斯酸介导的生物合成启发的不对称Diels-Alder环加成反应，以及涉及区域选择性Schenck烯反应，还原和脱水的过程，以实现仿生脱氢反应，从而产生所需的仿生氢。二烯前体。此外，非凡的串联分子间/分子间不对称Diels-Alder环加成反应过程被用于合成（-）-溴亚砜A。

  DOI：

  10.1002/anie.201404499

文献信息

• Design, Synthesis, and Biological Evaluation of Prenylated Chalcones as Vasorelaxant Agents
  作者：Xiaowu Dong、Jing Chen、Chaoyi Jiang、Tao Liu、Yongzhou Hu

  DOI：10.1002/ardp.200800229

  日期：2009.7

  Five prenylated chalcones and one allylated chalcone were prepared according to the analysis based on support vector machine (SVM) classification model. Most of the synthesized chalcones showed potent vasorelaxant activities through evaluation in aortic rings with the endothelium pre‐contracted by phenylephrine (PE), indicating that the experimental activities were in good agreement with the theoretical

  根据基于支持向量机(SVM)分类模型的分析，制备了5个异戊二烯化查耳酮和1个烯丙基化查耳酮。大多数合成的查尔酮通过评估主动脉环与去氧肾上腺素（PE）预收缩的内皮显示出有效的血管舒张活性，表明实验活性与理论活性非常吻合。这些化合物的构效关系表明，取代基模式和羟基的数量对其血管舒张活性至关重要，并且用烯丙基取代异戊二烯基保留了有效的活性。