4',5,7-tri(3-bromopropoxy)isoflavone | 862255-04-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4',5,7-tri(3-bromopropoxy)isoflavone
• 英文别名: 5,7-Bis(3-bromopropoxy)-3-[4-(3-bromopropoxy)phenyl]chromen-4-one
• CAS: 862255-04-7
• 化学式: C₂₄H₂₅Br₃O₅
• 分子量: 633.172
• InChiKey: DAVAPYJHDNEHRC-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C(Solv: acetone (67-64-1))
• 沸点：
  703.7±60.0 °C(Predicted)
• 密度：
  1.624±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4',5,7-tri(3-bromopropoxy)isoflavone 在 sodium hydroxide 作用下， 生成 1-[2,4-Bis(3-bromopropoxy)-6-hydroxyphenyl]-2-[4-(3-bromopropoxy)phenyl]ethanone
  参考文献：
  名称：

  Synthesis, crystal structure and antimicrobial activity of deoxybenzoin derivatives from genistein

  摘要：

  A series of deoxybenzoin derivatives from genistein were synthesized and their structures were elucidated by H-1 NMR, mass spectral data and micro analyses. The structures of 2, 7 and 10 were determined by single-crystal X-ray analysis. These obtained compounds were evaluated for their assayed antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescence and Staphylococcus aureus) and antifungal (Aspergillus niger, Candida albicans and Trichophyton rubrum) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium. bromide) method. Most compounds have displayed comparable antibacterial activity against bacterial. On the basis of the biological results, structure-activity relationships are discussed. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.05.013
• 作为产物：
  描述：

  染料木素 、 1,3-二溴丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以90%的产率得到4',5,7-tri(3-bromopropoxy)isoflavone
  参考文献：
  名称：

  Genistein derivatives as selective estrogen receptor modulators: Sonochemical synthesis and in vivo anti-osteoporotic action

  摘要：

  Genistein derivatives were synthesized from genistein through a facile sonochemical approach in high yields. The bioassay was performed on ovariectomized (OVX) rats in terms of bone mineral density (BMD) and the weight of bone ash (WBA) to lead to the discovery of eight novel genistein-based selective estrogen receptor modulators. Attention to the structure activity relationship disclosed that the newly introduced 2-hydroxyethylthio scaffolds were essential for the anti-ostcoporotic activity. Moreover, the anti-osteoporotic action of genistein, deprivable by methylation, could be restored and enhanced by subsequent sulfonation. The most promising compound was 4',5.7-tri[3-(2-hydroxyethylthio)propoxy]isoflavone displaying 24% (or 8%) increment in BMD and 31% (or 11%) increase in WBA of the femora relative to those discerned with the OVX (Or genistein) group. Acute toxicity test showed that none of the active compounds was acutely toxic. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.082