2'-hydroxy-5'-methoxymethoxy-3-bromo-chalcone | 1134396-10-3

• 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'-hydroxy-5'-methoxymethoxy-3-bromo-chalcone
• CAS: 1134396-10-3
• 化学式: C₁₇H₁₅BrO₄
• 分子量: 363.208
• InChiKey: JRXKWNCVZFPPEY-UHFFFAOYSA-N

物化性质

• 熔点：
  101-103 °C
• 沸点：
  530.1±50.0 °C(predicted)
• 密度：
  1.445±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-5'-methoxymethoxy-3-bromo-chalcone 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以55%的产率得到(+/-)-6-methoxymethoxy-3'-bromo-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
• 作为产物：
  描述：

  间溴苯甲醛 、 2'-hydroxy-5'-methoxymethoxyacetophenone 在 氢氧化钾 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以67%的产率得到2'-hydroxy-5'-methoxymethoxy-3-bromo-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

• Microwave-Assisted Mannich Reaction of 2-Hydroxy-chalcones
  作者：Xiaowu Dong、Tao Liu、Jing Chen、Huazhou Ying、Yongzhou Hu

  DOI：10.1080/00397910802431107

  日期：2009.1.28

  A series of Mannich base derivatives of 2-hydroxy-chalcones were obtained expediently in good to excellent yields by microwave-assisted Mannich reaction. The regioselectivity of the reaction occurred preferentially at the C-3 position of the 2-hydroxy-chalcone backbone. In comparison with conventional results, results from microwave possesses give better yields in shorter times. Further vasorelaxation assay showed that 2-hydroxy-3-((4-methylpiperazin-1-yl)methyl)-4,6-dimethoxymethoxy-3'-bromo-chalcone 8 significantly decreased maximal PE-induced contraction (Emax=1005.97%, EC50=10.20.51M).