(+/-)-4',5,7-trimethoxymethoxy-8-allyl-flavanone | 1134396-38-5

• 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: (+/-)-4',5,7-trimethoxymethoxy-8-allyl-flavanone
• 英文别名: 5,7-Bis(methoxymethoxy)-2-[4-(methoxymethoxy)phenyl]-8-prop-2-enyl-2,3-dihydrochromen-4-one
• CAS: 1134396-38-5
• 化学式: C₂₄H₂₈O₈
• 分子量: 444.482
• InChiKey: ABPWXBYBLGZHSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+/-)-4',5,7-trimethoxymethoxy-8-allyl-flavanone 在 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 以68%的产率得到8-allylnaringenin
  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-4,4',6'-trimethoxymethoxy-3'-allyl-chalcone 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以52%的产率得到(+/-)-4',5,7-trimethoxymethoxy-8-allyl-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

文献信息

• [EN] NARINGENIN DERIVATIVES WITH SELECTIVITY ON ERS<br/>[FR] DERIVES DE NARINGENINE PRESENTANT UNE SELECTIVITE SUR DES ERS
  申请人：UNIV GENT

  公开号：WO2007053915A2

  公开（公告）日：2007-05-18

  [EN] The present invention relates to naringenin derivatives with selective anti¬ estrogenic activity and their use in the treatment of diseases or disorders estrogen- deficiency dependent disorders, diseases with excessive estrogen production or conditions benefiting from modulated estrogen production.
  [FR] L'invention concerne des dérivés de naringénine à activité anti-oestrogène sélective, et leur utilisation dans le traitement de maladies ou de troubles liés à des déficiences en oestrogène, de maladies à production excessive en oestrogène, ou d'états résultant d'une production d'oestrogène modulée.