3',5'-bis-(3,5-dichlorobenzyloxy)-7-(2,3-epoxypropoxy)flavone | 1374792-16-1

• 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',5'-bis-(3,5-dichlorobenzyloxy)-7-(2,3-epoxypropoxy)flavone
• 英文别名: 2-[3,5-Bis[(3,5-dichlorophenyl)methoxy]phenyl]-7-(oxiran-2-ylmethoxy)chromen-4-one
• CAS: 1374792-16-1
• 化学式: C₃₂H₂₂Cl₄O₆
• 分子量: 644.335
• InChiKey: YKVPYGTYJQPQGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3',5'-bis-(3,5-dichlorobenzyloxy)-7-(2,3-epoxypropoxy)flavone 、 异丙胺 以 甲醇 为溶剂， 反应 6.0h， 以52%的产率得到3',5'-bis(3,5-dichlorobenzyloxy)-7-[2-hydroxy-3-(iso-propylamino)propoxy]flavone
  参考文献：
  名称：

  Flavone-Based Novel Antidiabetic and Antidyslipidemic Agents

  摘要：

  The hybrid congeners 62-90 of 6- and 7-hydroxyflavones with aminopropanol have been synthesized and evaluated for their antidiabetic activity in sucrose-challenged low-dosed streptozotocin (STZ)-induced diabetic rats and db/db mice. The optical enantiomers 70a, 706, 90a, and 906 of two congeners 70 and 90 exhibiting consistent antidiabetic and antidyslipidemic activities were also prepared, and their antidiabetic activity results indicate its association mainly with S isomers. These compounds also lower cholesterol and TG profiles while improving high-density lipoprotein cholesterol to CHOL ratio in db/db mice. The bioavailability of compound 70 and its isomer varies between 27 and 29% whereas that of the more polar compound 90a is poor as determined in rat by oral and intraperitoneal administrations.

  DOI：

  10.1021/jm201107g
• 作为产物：
  描述：

  二羟基苯甲酸乙酯 在 potassium carbonate 、 sodium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 异丙醇 、 丙酮 为溶剂， 反应 3.0h， 生成 3',5'-bis-(3,5-dichlorobenzyloxy)-7-(2,3-epoxypropoxy)flavone
  参考文献：
  名称：

  Flavone-Based Novel Antidiabetic and Antidyslipidemic Agents

  摘要：

  The hybrid congeners 62-90 of 6- and 7-hydroxyflavones with aminopropanol have been synthesized and evaluated for their antidiabetic activity in sucrose-challenged low-dosed streptozotocin (STZ)-induced diabetic rats and db/db mice. The optical enantiomers 70a, 706, 90a, and 906 of two congeners 70 and 90 exhibiting consistent antidiabetic and antidyslipidemic activities were also prepared, and their antidiabetic activity results indicate its association mainly with S isomers. These compounds also lower cholesterol and TG profiles while improving high-density lipoprotein cholesterol to CHOL ratio in db/db mice. The bioavailability of compound 70 and its isomer varies between 27 and 29% whereas that of the more polar compound 90a is poor as determined in rat by oral and intraperitoneal administrations.

  DOI：

  10.1021/jm201107g

文献信息

• Flavone-Based Novel Antidiabetic and Antidyslipidemic Agents
  作者：Alok K. Verma、Himanshu Singh、Mavurapu Satyanarayana、Swayam P. Srivastava、Priti Tiwari、Amar B. Singh、Anil K. Dwivedi、Shio K. Singh、Mukesh Srivastava、Chandishwar Nath、Ram Raghubir、Arvind K. Srivastava、Ram Pratap

  DOI：10.1021/jm201107g

  日期：2012.5.24

  The hybrid congeners 62-90 of 6- and 7-hydroxyflavones with aminopropanol have been synthesized and evaluated for their antidiabetic activity in sucrose-challenged low-dosed streptozotocin (STZ)-induced diabetic rats and db/db mice. The optical enantiomers 70a, 706, 90a, and 906 of two congeners 70 and 90 exhibiting consistent antidiabetic and antidyslipidemic activities were also prepared, and their antidiabetic activity results indicate its association mainly with S isomers. These compounds also lower cholesterol and TG profiles while improving high-density lipoprotein cholesterol to CHOL ratio in db/db mice. The bioavailability of compound 70 and its isomer varies between 27 and 29% whereas that of the more polar compound 90a is poor as determined in rat by oral and intraperitoneal administrations.