1-甲基-3-(4-羟基苯基)-1H-喹啉-4-酮 | 1053190-07-0

• 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
• 中文名称: 1-甲基-3-(4-羟基苯基)-1H-喹啉-4-酮
• 英文名称: 1-methyl-3-(4-hydroxyphenyl)-1H-quinolin-4-one
• 英文别名: 3-(4-hydroxyphenyl)-1-methyl-1H-quinolin-4-one；3-(4-hydroxyphenyl)-1-methylquinolin-4(1H)-one；3-(4-Hydroxyphenyl)-1-methylquinolin-4-one
• CAS: 1053190-07-0
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: RCNGXVPUFFXTGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-[2-[3-(4-methoxyphenyl)-1-oxo-2-propenyl]phenyl]acetamide 在 盐酸 、 thallium(III) nitrate trihydrate 、 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 81.42h， 生成 1-甲基-3-(4-羟基苯基)-1H-喹啉-4-酮
  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.
• Ohmic Heating-Assisted Synthesis of 3-Arylquinolin-4(1<i>H</i>)-ones by a Reusable and Ligand-Free Suzuki–Miyaura Reaction in Water
  作者：Joana Pinto、Vera L. M. Silva、Ana M. G. Silva、Luís M. N. B. F. Santos、Artur M. S. Silva

  DOI：10.1021/acs.joc.5b00793

  日期：2015.7.2

  Potential bioactive 3-arylquinolin-4(1H)-ones were synthesized under ohmic heating using an efficient, reusable, and ligand-free protocol developed for the Suzuki-Miyaura coupling of 1-substituted-3-iodoquinolin-4(1H)-ones with several boronic acids in water using Pd(OAc)(2) as a catalyst and tetrabutylammonium bromide (TBAB) as the phase transfer catalyst. Good substrate generality, ease of execution, short reaction time, and practicability make this method exploitable for the generation of libraries of B ring-substituted 3-arylquinolin-4(1H)-ones. After a simple workup, the Pd/catalyst-H2O-TBAB system could be reused for at least seven cycles without significant loss of activity.
• 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.