(E)-1-(3-bromophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one | 1002798-51-7

• 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: (E)-1-(3-bromophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• CAS: 1002798-51-7
• 化学式: C₁₆H₁₃BrO₃
• 分子量: 333.181
• InChiKey: NDMIUEXMLAKNRS-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-bromophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one 、 3-氟苯基硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.33h， 以76.58%的产率得到(E)-1-(3′-fluoro-[1,1′-biphenyl]-3-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of biaryl-based chalcones and their potential in TNFα-induced nuclear factor-κB activation inhibition

  摘要：

  A series of biaryl-based chalcones were designed as a combination of the natural chalcone and biphenyl moieties, and synthesized by two step chemistry involving Knoevenagel reaction and microwave assistant Suzuki coupling. Sulforhodamine B (SRB) assay was performed to evaluate the cell viability inhibitory abilities of these compounds against five cancer cell lines (A549, CNE2, SW480, MCF-7, and HepG2) from different tissues. Their Nuclear Factor-kappa B (NF-kappa B) nuclear translocation inhibitory activities were further investigated by High Content Analysis (HCA) based assay. Most of the compounds showed moderate to strong anticancer and NF-kappa B nuclear translocation inhibition activities and potent compounds were found. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.023
• 作为产物：
  描述：

  异香兰素 、 3'-溴苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以85.62%的产率得到(E)-1-(3-bromophenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of biaryl-based chalcones and their potential in TNFα-induced nuclear factor-κB activation inhibition

  摘要：

  A series of biaryl-based chalcones were designed as a combination of the natural chalcone and biphenyl moieties, and synthesized by two step chemistry involving Knoevenagel reaction and microwave assistant Suzuki coupling. Sulforhodamine B (SRB) assay was performed to evaluate the cell viability inhibitory abilities of these compounds against five cancer cell lines (A549, CNE2, SW480, MCF-7, and HepG2) from different tissues. Their Nuclear Factor-kappa B (NF-kappa B) nuclear translocation inhibitory activities were further investigated by High Content Analysis (HCA) based assay. Most of the compounds showed moderate to strong anticancer and NF-kappa B nuclear translocation inhibition activities and potent compounds were found. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.023

文献信息

• Synthesis and cytotoxicity evaluation of biaryl-based chalcones and their potential in TNFα-induced nuclear factor-κB activation inhibition
  作者：Yinglin Zuo、Yi Yu、Shuni Wang、Weiyan Shao、Binhua Zhou、Li Lin、Zhuoyu Luo、Ruogu Huang、Jun Du、Xianzhang Bu

  DOI：10.1016/j.ejmech.2012.02.023

  日期：2012.4

  A series of biaryl-based chalcones were designed as a combination of the natural chalcone and biphenyl moieties, and synthesized by two step chemistry involving Knoevenagel reaction and microwave assistant Suzuki coupling. Sulforhodamine B (SRB) assay was performed to evaluate the cell viability inhibitory abilities of these compounds against five cancer cell lines (A549, CNE2, SW480, MCF-7, and HepG2) from different tissues. Their Nuclear Factor-kappa B (NF-kappa B) nuclear translocation inhibitory activities were further investigated by High Content Analysis (HCA) based assay. Most of the compounds showed moderate to strong anticancer and NF-kappa B nuclear translocation inhibition activities and potent compounds were found. (C) 2012 Elsevier Masson SAS. All rights reserved.