7-hydroxy-3-(4-hydroxyphenyl)-1-(3-methylbutyl)-1H-quinolin-4-one | 1621002-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-hydroxy-3-(4-hydroxyphenyl)-1-(3-methylbutyl)-1H-quinolin-4-one
• 英文别名: 7-Hydroxy-3-(4-hydroxyphenyl)-1-(3-methylbutyl)quinolin-4-one；7-hydroxy-3-(4-hydroxyphenyl)-1-(3-methylbutyl)quinolin-4-one
• CAS: 1621002-95-6
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: GCCLXYLUUWWFPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2’-氨基-4’-甲氧基苯乙酮 在 吡啶 、 盐酸 、 thallium(III) nitrate trihydrate 、 氢溴酸 、 甲酸铵 、 palladium(II) hydroxide 、 sodium hydride 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 39.42h， 生成 7-hydroxy-3-(4-hydroxyphenyl)-1-(3-methylbutyl)-1H-quinolin-4-one
  参考文献：
  名称：

  Design and synthesis of azaisoflavone analogs as phytoestrogen mimetics

  摘要：

  A series of azaisoflavone analogs were designed and synthesized and their transactivation activities and binding affinities for ER alpha and ER beta were investigated. Among these compounds, 2b and 3a were the most potent with 6.5 and 1.1 mu M of EC50, respectively. Molecular modeling study showed putative binding modes of the compound 3a in the active site of ER alpha and ER beta, which were similar with that of genistein and provided insight of the effect of N-alkyl substitution of azaisoflavones on ER beta activity. Also, a biphasic effect of azaisoflavone analogs on MCF-7 cell growth depending on their concentrations was investigated. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.030

文献信息

• Design and synthesis of azaisoflavone analogs as phytoestrogen mimetics
  作者：Hyo Jin Gim、Hua Li、So Ra Jung、Yong Joo Park、Jae-Ha Ryu、Kyu Hyuck Chung、Raok Jeon

  DOI：10.1016/j.ejmech.2014.07.030

  日期：2014.10

  A series of azaisoflavone analogs were designed and synthesized and their transactivation activities and binding affinities for ER alpha and ER beta were investigated. Among these compounds, 2b and 3a were the most potent with 6.5 and 1.1 mu M of EC50, respectively. Molecular modeling study showed putative binding modes of the compound 3a in the active site of ER alpha and ER beta, which were similar with that of genistein and provided insight of the effect of N-alkyl substitution of azaisoflavones on ER beta activity. Also, a biphasic effect of azaisoflavone analogs on MCF-7 cell growth depending on their concentrations was investigated. (C) 2014 Elsevier Masson SAS. All rights reserved.