3-O-[(E)-4-(4-(tert-butyl)phenyl)-2-oxobut-3-en-1-yl]kaempferol | 1338577-22-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-O-[(E)-4-(4-(tert-butyl)phenyl)-2-oxobut-3-en-1-yl]kaempferol
• 英文别名: 3-[(E)-4-(4-tert-butylphenyl)-2-oxobut-3-enoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• CAS: 1338577-22-2
• 化学式: C₂₉H₂₆O₇
• 分子量: 486.521
• InChiKey: RKOWFEVJFHRPSH-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-t-butylbenzylideneacetone 在 2-pyrrolidinone hydrotribromide 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 1.5h， 生成 3-O-[(E)-4-(4-(tert-butyl)phenyl)-2-oxobut-3-en-1-yl]kaempferol
  参考文献：
  名称：

  Synthesis and biological activity of novel tiliroside derivants

  摘要：

  A series of new tiliroside derivatives were synthesized and characterized by analytical H-1 NMR, C-13 NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5'-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.059

文献信息

• FLAVONE DERIVATIVES AND THEIR PREPARATIVE METHOD AND MEDICAL USE
  申请人：Duan Hongquan

  公开号：US20130231492A1

  公开（公告）日：2013-09-05

  Flavone derivatives, preparative method of the derivatives and use thereof as medicaments for treating diabetes. The structure of the derivatives is presented by formula 1: In the structure, R 1 and R 2 , which are identical or not, represent hydrogen atom, halogen, cyano, hydroxyl, trifluoromethyl, thio-methyl, benzyloxy, C1-C8 linear chain or branch chain alkyl, C1-C8 linear chain or branch chain alkoxy. The pharmacological test indicates that the flavone derivatives can significantly increase the glucose consumption of Hep-G2 cell with insulin resistance activity, promote translocation of glucose transporter 4 of skeletal muscle cells (L6GLUT4myc) at different level, and significantly increase glucose intake and utilization by cells. The test proves the fact for the first time that the flavone derivatives can significantly promote translocation of glucose transporter 4 of skeletal muscle cells, and one of the mechanisms for treating diabetes is activating the cell AMPK phosphorylation and phosphorylating the downstream ACC.

  黄酮衍生物、其衍生物的制备方法及其用作治疗糖尿病的药物。衍生物的结构由公式1表示：在结构中，R1和R2相同或不相同，代表氢原子、卤素、氰基、羟基、三氟甲基、硫甲基、苄氧基、C1-C8直链或支链烷基、C1-C8直链或支链烷氧基。药理测试表明，黄酮衍生物能显著增加具有胰岛素抵抗活性的Hep-G2细胞的葡萄糖消耗量，以不同水平促进骨骼肌细胞（L6GLUT4myc）的葡萄糖转运蛋白4的转位，并显著增加细胞对葡萄糖的摄取和利用。该测试首次证实了黄酮衍生物能显著促进骨骼肌细胞的葡萄糖转运蛋白4的转位，并且治疗糖尿病的机制之一是通过激活细胞AMPK磷酸化和磷酸化下游的ACC。
• US8946457B2
  申请人：——

  公开号：US8946457B2

  公开（公告）日：2015-02-03
• Synthesis and biological activity of novel tiliroside derivants
  作者：Nan Qin、Chun-Bao Li、Mei-Na Jin、Li-Huan Shi、Hong-Quan Duan、Wen-Yan Niu

  DOI：10.1016/j.ejmech.2011.07.059

  日期：2011.10

  A series of new tiliroside derivatives were synthesized and characterized by analytical H-1 NMR, C-13 NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5'-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes. (C) 2011 Elsevier Masson SAS. All rights reserved.