3',4'-dibenzyloxy-6-(2,3-epoxypropoxy)flavone | 883242-56-6

• 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',4'-dibenzyloxy-6-(2,3-epoxypropoxy)flavone
• 英文别名: 3',4'-Dibenzyloxy-6-(2,3-epoxy-propoxy)-flavone；2-[3,4-bis(phenylmethoxy)phenyl]-6-(oxiran-2-ylmethoxy)chromen-4-one
• CAS: 883242-56-6
• 化学式: C₃₂H₂₆O₆
• 分子量: 506.555
• InChiKey: ONUYWAXFCBKIJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  38
• 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',4'-dibenzyloxy-6-(2,3-epoxypropoxy)flavone 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 3',4'-dihydroxy-6-[3-(tert-butylamino)-2-hydroxy-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：

  原儿茶酸 在 硫酸 、 sodium hydride 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 、 丙酮 为溶剂， 反应 20.5h， 生成 3',4'-dibenzyloxy-6-(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

• [EN] OXY SUBSTITUTED FLAVONES AS ANTIHYPERGLYCEMIC AND ANTIDYSLIPIDEMIC AGENTS<br/>[FR] FLAVONES SUBSTITUES PAR HYDROXY UTILISES EN TANT QU'AGENTS ANTI-HYPERGLYCEMIQUES ET ANTI-DYSLIPIDEMIQUES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2006040621A1

  公开（公告）日：2006-04-20

  The present invention provides novel substituted flavone derivatives which exhibit anti­ hyperglycemic and antidyslipedemic activity. The invention also provides a method for controlling type ii diabetes and associated hyperlipidemic conditions in a mammal by administering compound of the present invention and compositions containing these derivatives.

  本发明提供了新颖的取代黄酮衍生物，表现出抗高血糖和抗血脂异常活性。该发明还提供了一种通过给予本发明化合物和含有这些衍生物的组合物来控制哺乳动物中II型糖尿病和相关高血脂症状的方法。
• Oxy substituted flavones as antihyperglycemic and antidyslipidemic agents
  申请人：Pratap Ram

  公开号：US20060178373A1

  公开（公告）日：2006-08-10

  The present invention provides novel substituted flavone derivatives which exhibit anti-hyperglycemic and antidyslipedemic activity. The invention also provides a method for controlling type II diabetes and associated hyperlipidemic conditions in a mammal by administering compound of the present invention and compositions containing these derivatives.

  本发明提供了一种新型的取代黄酮衍生物，该衍生物表现出抗高血糖和抗血脂异常的活性。本发明还提供了一种通过给予本发明化合物和含有这些衍生物的组合物来控制哺乳动物的II型糖尿病和相关高脂血症状的方法。
• OXY SUBSTITUTED FLAVONES AS ANTIHYPERGLYCEMIC AND ANTIDYSLIPIDEMIC AGENTS
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：EP1807408A1

  公开（公告）日：2007-07-18
• US7635779B2
  申请人：——

  公开号：US7635779B2

  公开（公告）日：2009-12-22