2-(2,4-二羟基苯基)-5,7-二羟基-6-(3-甲基丁-2-烯基)苯并吡喃-4-酮 | 3162-09-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-(2,4-二羟基苯基)-5,7-二羟基-6-(3-甲基丁-2-烯基)苯并吡喃-4-酮
• 中文别名: 桂木生黄素
• 英文名称: artocarpesin
• 英文别名: 2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
• CAS: 3162-09-2
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: YWUVFGZTDLJVCR-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  275-276°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2914501900

反应信息

• 作为反应物：
  描述：

  2-(2,4-二羟基苯基)-5,7-二羟基-6-(3-甲基丁-2-烯基)苯并吡喃-4-酮 在 Tween 80 作用下， 以 水 为溶剂， 反应 168.0h， 以8 mg的产率得到4H-1-苯并吡喃-4-酮,6-[(1S,5S,6R)-6-[2,4-二羟基-3-(3-甲基-2-丁烯-1-基)苯甲酰]-5-(2,4-二羟基苯基)-3-甲基-2-环己烯-1-基]-2-(2,4-二羟基苯基)-5,7-二羟基-
  参考文献：
  名称：

  借助桑树细胞培养物的酶系统，一种新的测定青蒿素I（旋光Diels-Alder型加合物）结构的新颖方法

  摘要：

  利用桑树桑树细胞培养物的酶系统，建立了印尼桑树（Artocarpus heterophyllus）的光学活性Diels-Alder型加合物的结构，该酶专门产生天然的Diels-Alder型加合物，并具有光谱学证据。 。

  DOI：

  10.1039/c39920001177
• 作为产物：
  描述：

  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 吡啶 、 盐酸 、 水 、 碘 、 sodium acetate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 72.0h， 生成 2-(2,4-二羟基苯基)-5,7-二羟基-6-(3-甲基丁-2-烯基)苯并吡喃-4-酮
  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

文献信息

• GuA6DT, a Regiospecific Prenyltransferase from<i>Glycyrrhiza uralensis</i>, Catalyzes the 6-Prenylation of Flavones
  作者：Jianhua Li、Ridao Chen、Ruishan Wang、Xiao Liu、Dan Xie、Jianhua Zou、Jungui Dai

  DOI：10.1002/cbic.201402160

  日期：2014.7.21

  Regiospecific prenylation: The flavonoid prenyltransferase GuA6DT from Glycyrrhiza uralensis, is responsible for the prenylation of flavones. Hydroxy groups at both C‐5 and C‐7 positions are critical for the prenylation, and the prenylation regiospecifically occurs at C‐6. GuA6DT would be useful as an environmentally friendly and efficient biocatalyst for the preparation of bioactive prenylflavones

  区域特异性异戊烯基化：来自甘草的黄酮类异戊二烯基戊烯基转移酶GuA6DT负责黄酮的异戊烯基化。在C-5和C-7位置上的羟基对于异戊二烯化至关重要，异戊二烯的区域特异性发生在C-6处。GuA6DT可用作制备生物活性异黄酮的环保和高效生物催化剂。
• Mechanism on One-sided Wessely-Moser Rearrangement Reaction
  作者：Taro Nomura、Kazuki Shinomiya、Yoshio Hano

  DOI：10.3987/com-99-8827

  日期：——
• Pharmacophore identification, virtual screening and biological evaluation of prenylated flavonoids derivatives as PKB/Akt1 inhibitors
  作者：Xiaowu Dong、Xinglu Zhou、Hui Jing、Jianzhong Chen、Tao Liu、Bo Yang、Qiaojun He、Yongzhou Hu

  DOI：10.1016/j.ejmech.2011.10.006

  日期：2011.12

  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.
• A novel way of determining the structure of artonin I, an optically active Diels–Alder type adduct, with the aid of an enzyme system of Morus alba cell cultures
  作者：Yoshio Hano、Miwa Aida、Taro Nomura、Shinichi Ueda

  DOI：10.1039/c39920001177

  日期：——

  The structure of artonin I, an optically active Diels–Alder type adduct from Artocarpus heterophyllus, an Indonesian moraceous plant, was established utilizing the enzyme system of Morus alba cell cultures which specifically produce the natural Diels–Alder type adducts, as well as spectroscopic evidence.

  利用桑树桑树细胞培养物的酶系统，建立了印尼桑树（Artocarpus heterophyllus）的光学活性Diels-Alder型加合物的结构，该酶专门产生天然的Diels-Alder型加合物，并具有光谱学证据。 。