(S)-3',5'-dibenzyloxy-7-(2,3-epoxy-propoxy)-flavone | 1006392-15-9

• 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: (S)-3',5'-dibenzyloxy-7-(2,3-epoxy-propoxy)-flavone
• 英文别名: (S)-(+)-7-(2,3-epoxy-propoxy)-3',5'-dibenzyloxy flavone；2-[3,5-bis(phenylmethoxy)phenyl]-7-[[(2S)-oxiran-2-yl]methoxy]chromen-4-one
• CAS: 1006392-15-9
• 化学式: C₃₂H₂₆O₆
• 分子量: 506.555
• InChiKey: GOUCKLACVIBWAJ-MUUNZHRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 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：

  (S)-3',5'-dibenzyloxy-7-(2,3-epoxy-propoxy)-flavone 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (S)-(-)-3',5'-dihydroxy-7-[3-(iso-propylamino)-2-hydroxypropoxy]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 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 异丙醇 、 丙酮 为溶剂， 反应 16.0h， 生成 (S)-3',5'-dibenzyloxy-7-(2,3-epoxy-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

文献信息

• R-(-) / S-(+)-7-[3-N SUBSTITUTED AMINO-2 HYDROXYPROPOXY] FLAVONES
  申请人：Pratap Ram

  公开号：US20110077294A1

  公开（公告）日：2011-03-31

  The present invention provides an optically active compound of general formula (I) and salts thereof: wherein R′ is selected from a group consisting of t-butyl amine, n-butylamine, iso-butylamine, iso-propyl amine, 4-phenyl-piperazine-1-ylamine, 4-(2-methoxyphenyl)-piperazin-1-ylamine, and 3,4-dimethoxy phenethyl amine; wherein R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, methyl or iso pentenyl; R 4 , R 5 and R 6 are selected from the group consisting of Oil, O-alkyl, O-benzyl, O-substituted phenyl or combination thereof.

  本发明提供了一种具有通式（I）的光学活性化合物及其盐：其中R′选自由t-丁基胺、正丁胺、异丁胺、异丙基胺、4-苯基哌嗪-1-胺、4-(2-甲氧基苯基)-哌嗪-1-胺和3,4-二甲氧基苯乙基胺组成的群体；其中R1、R2和R3选自由氢、甲基或异戊烯基组成的群体；R4、R5和R6选自由Oil、O-烷基、O-苯甲基、O-取代苯基或其组合。
• WO2008/18089
  申请人：——

  公开号：——

  公开（公告）日：——
• S-(+)-7-[3-N-SUBSTITUTED AMINO-2-HYDROXYPROPOXY]FLAVONES
  申请人：Council of Scientific and Industrial Research

  公开号：EP2057137B1

  公开（公告）日：2013-10-23
• R-(-) / S-(+)-7-[3-N-SUBSTITUTED AMINO-2-HYDROXYPROPOXY]FLAVONES
  申请人：Council of Scientific and Industrial Research

  公开号：EP2057137A1

  公开（公告）日：2009-05-13
• [EN] R-(-) / S-(+)-7-[3-N-SUBSTITUTED AMINO-2-HYDROXYPROPOXY] FLAVONES<br/>[FR] R-(-) OU S-(+)-7-[3-N-(AMINO SUBSTITUÉ)-2-HYDROXYPROPOXY]FLAVONES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2008018089A1

  公开（公告）日：2008-02-14

  [EN] The present invention provides an optically active compound of general formula (I) and salts thereof: wherein R' is selected from a group consisting of t-butyl amine, n-butylamine, iso- butylamine, iso-propyl amine, 4-phenyl-piperazine-1-ylamine, 4-(2-methoxyphenyl)- piperazin-1-ylamine, and 3, 4-dimethoxy phenethyl amine; wherein R₁, R₂ and R₃ are selected from the group consisting of hydrogen, methyl or iso pentenyl; R₄, R₅ and R₆ are selected from the group consisting of OH, O-alkyl, O-benzyl, O-substituted phenyl or combination thereof.
  [FR] La présente invention concerne un composé optiquement actif de formule générale (I) et des sels dudit composé. Dans la formule (I), R' est choisi dans le groupe comprenant la t-butylamine, la n-butylamine, l'isobutylamine, l'isopropylamine, la 4-phénylpipérazine-1-ylamine, la 4-(2-méthoxyphényl)pipérazin-1-ylamine et la 3,4-diméthoxyphénéthylamine; R₁, R₂ et R₃ représentent un atome d'hydrogène, un groupe méthyle ou un groupe isopentényle; R₄, R₅ et R₆ représentent un groupe OH, O-alkyle, O-benzyle, O-(phényle substitué) ou une de leurs combinaisons.