1-(2-amino-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one | 850804-18-1

• 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: 1-(2-amino-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(2-amino-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)propenone
• CAS: 850804-18-1
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: YFVSQULIJASZCA-UHFFFAOYSA-N

物化性质

• 沸点：
  537.9±50.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.78
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(2-amino-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 在 吡啶 、 thallium(III) nitrate trihydrate 作用下， 反应 7.25h， 生成 N-{2-[3,3-dimethoxy-2-(4-methoxyphenyl)propionyl]-3,5-dimethoxyphenyl}acetamide
  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
• 作为产物：
  描述：

  3,5-二甲氧基苯胺 在 aluminum (III) chloride 、 三氯化硼 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 30.5h， 生成 1-(2-amino-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-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

• Synthesis of azaisoflavones and their inhibitory activities of NO production in activated microglia
  作者：Guo Hua Jin、Sang Keun Ha、Hye Min Park、Bomi Kang、Sun Yeou Kim、Hee-Do Kim、Jae-Ha Ryu、Raok Jeon

  DOI：10.1016/j.bmcl.2008.05.106

  日期：2008.7

  A series of azaisoflavones were synthesized and their biological activities were evaluated for nitric oxide (NO) production and inducible NO synthase (iNOS) expression in BV-2 microglia cell lines. Among these compounds, compound 8d was the most potent with IC50 7.83 mu M for inhibition of NO production. Also, compound 8d inhibited expression of iNOS in LPS-induced BV2 cells. This result suggests that compound 8d inhibited the production of NO by suppressing the expression of iNOS. (c) 2008 Elsevier Ltd. All rights reserved.