甘草宁O | 129145-53-5

• 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: 甘草宁O
• 英文名称: 2-[3,4-dihydroxyphenyl]-5,7-dihydroxy-6-[3-methylbut-2-enyl]chromone
• 英文别名: 3',4',5,7-tetrahydroxy-6-(3,3-dimethylallyl)flavone；6-dimethylallylluteolin；demethyltorosaflavone D；6-C-prenyl luteolin；6-C-prenylluteolin；Gancaonin O；2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
• CAS: 129145-53-5
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: AFJYQKPCJLMHCC-UHFFFAOYSA-N

物化性质

• 熔点：
  245-248 °C
• 沸点：
  633.4±55.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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

反应信息

• 作为产物：
  描述：

  3,4-双(甲氧基甲氧基)苯甲醛 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 甘草宁O
  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。
• Catalytic prenylation of natural polyphenols
  作者：Yi Du、Iman Korchi、Aleksandr E. Rubtsov、Andrei V. Malkov

  DOI：10.1039/d3nj04371a

  日期：——

  Prenylated polyphenols occur naturally and exhibit biological activity superior to the ubiquitous parent polyphenols. However, their low abundance limits the wider application of these derivatives. In this work, we present an expedient, single-step catalytic protocol for introducing terpene fragments into the aromatic rings of the widely available natural stilbenoids and flavonoids to upgrade their

  异戊二烯化多酚天然存在，并表现出优于普遍存在的母体多酚的生物活性。然而，它们的低丰度限制了这些衍生物的更广泛应用。在这项工作中，我们提出了一种便捷的单步催化方案，用于将萜烯片段引入广泛使用的天然二苯乙烯类化合物和黄酮类化合物的芳环中，以提高其治疗潜力。
• Treatment of bladder and urinary tract cancers
  申请人：The Regents of the University of California

  公开号：US20040259813A1

  公开（公告）日：2004-12-23

  Compositions of matter and methods wherein chalcone and flavone derivatives are administered to human or veterinary patients for the treatment of bladder or urinary tract cancer. Compounds of the invention include 2′-hydroxy-4,4′,6′-trimethoxychalcone (Flavokawain A).

  向人类或兽类患者施用查尔酮和黄酮衍生物治疗膀胱癌或尿道癌的物质组合物和方法。本发明的化合物包括 2′-羟基-4,4′,6′-三甲氧基查尔酮（Flavokawain A）。
• US7326734B2
  申请人：——

  公开号：US7326734B2

  公开（公告）日：2008-02-05
• 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.