(+/-)-7-methoxymethoxy-3',4'-methylenedioxy-flavanone | 1134396-29-4

• 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: (+/-)-7-methoxymethoxy-3',4'-methylenedioxy-flavanone
• CAS: 1134396-29-4
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: GHBQEDHGMLYFRR-UHFFFAOYSA-N

物化性质

• 沸点：
  514.9±50.0 °C(predicted)
• 密度：
  1.334±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+/-)-7-methoxymethoxy-3',4'-methylenedioxy-flavanone 在 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 以78%的产率得到7-Hydroxy-3',4'-methylendioxyflavanon
  参考文献：
  名称：

  Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents

  摘要：

  A series of flavonoid derivatives were designed, synthesized. Their vasorelaxant activities were evaluated experimentally against rat aorta rings pretreated with phenylephrine (PE). Among them, 6-hydroxy-8-allyl- 4'-chloro-flavanone 8q exhibited the highest vasodilatory activity (EC50 = 4.6 mu M, E-max = 95.1%). The 3D-QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method, and a statistically reliable model with good predictive power (r(2) = 0.872 and q(cv)(2) = 0.496) was established. The contour plots of CoMFA model provide a good insight into the structure-activity relationships of these compounds and may be used to design more potent flavonoids derivatives as vasorelaxant agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.052
• 作为产物：
  描述：

  2'-hydroxy-4'-methoxymethoxy-3,4-methylenedioxy-chalcone 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以68%的产率得到(+/-)-7-methoxymethoxy-3',4'-methylenedioxy-flavanone
  参考文献：
  名称：

  Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents

  摘要：

  A series of flavonoid derivatives were designed, synthesized. Their vasorelaxant activities were evaluated experimentally against rat aorta rings pretreated with phenylephrine (PE). Among them, 6-hydroxy-8-allyl- 4'-chloro-flavanone 8q exhibited the highest vasodilatory activity (EC50 = 4.6 mu M, E-max = 95.1%). The 3D-QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method, and a statistically reliable model with good predictive power (r(2) = 0.872 and q(cv)(2) = 0.496) was established. The contour plots of CoMFA model provide a good insight into the structure-activity relationships of these compounds and may be used to design more potent flavonoids derivatives as vasorelaxant agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.052