2',4',6'-trihydroxy-3,4-methylenedioxy-chalcone | 58344-59-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2',4',6'-trihydroxy-3,4-methylenedioxy-chalcone
• 英文别名: 3-(1,3-benzodioxol-5-yl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• CAS: 58344-59-5
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: HYSPKAWQLSPCMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  96.22
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2',4',6'-trihydroxy-3,4-methylenedioxy-chalcone 、 1,2-二溴乙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以67%的产率得到3-(benzo[d][1,3]dioxol-5-yl)-1-(2,4,6-tris(2-bromoethoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  新型杂化查尔酮衍生物作为血管舒张剂的合成及生物学评价

  摘要：

  为了进一步改善查尔酮的血管舒张活性，基于分子杂交策略设计合成了九种杂化查尔酮衍生物，它们与一氧化氮（NO）供体或1,4-二氢吡啶基（1,4-DHP）部分共轭。他们的血管舒张活性被评估在主动脉环与苯肾上腺素（PE）预收缩的内皮细胞。所有这些化合物均表现出优选的血管舒张活性，比其母体化合物更有效。化合物8c和15c是最有效的化合物，将成为开发新型血管松弛剂的有前途的结构模板。

  DOI：

  10.1016/j.ejmech.2010.05.054
• 作为产物：
  描述：

  2'-hydroxy-4',6'-dimethoxymethoxy-3,4-methylenedioxy-chalcone 在 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 以74%的产率得到2',4',6'-trihydroxy-3,4-methylenedioxy-chalcone
  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

• Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents
  作者：Xiaowu Dong、Tao Liu、Jingying Yan、Peng Wu、Jing Chen、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.11.052

  日期：2009.1

  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.
• Synthesis and biological evaluation of novel hybrid chalcone derivatives as vasorelaxant agents
  作者：Xiaowu Dong、Lilin Du、Zhichao Pan、Tao Liu、Bo Yang、Yongzhou Hu

  DOI：10.1016/j.ejmech.2010.05.054

  日期：2010.9

  the vasorelaxant activities of chalcones, nine hybrid chalcone derivatives conjugated with nitric oxide (NO) donor or 1,4-dihydropyridyl (1,4-DHP) moiety were designed and synthesized based on molecular hybridization strategy. Their vasorelaxant activities were evaluated in aortic rings with endothelium pre-contracted with phenylephrine (PE). All of these compounds showed preferable vasorelaxant activities

  为了进一步改善查尔酮的血管舒张活性，基于分子杂交策略设计合成了九种杂化查尔酮衍生物，它们与一氧化氮（NO）供体或1,4-二氢吡啶基（1,4-DHP）部分共轭。他们的血管舒张活性被评估在主动脉环与苯肾上腺素（PE）预收缩的内皮细胞。所有这些化合物均表现出优选的血管舒张活性，比其母体化合物更有效。化合物8c和15c是最有效的化合物，将成为开发新型血管松弛剂的有前途的结构模板。