5,7-dimethoxy-3-(4-methoxyphenyl)-1H-quinolin-4-one | 190774-10-8

• 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: 5,7-dimethoxy-3-(4-methoxyphenyl)-1H-quinolin-4-one
• 英文别名: 5,7-dimethoxy-3-(4-methoxyphenyl)quinolin-4(1H)-one；5,7-Dimethoxy-3-(4-methoxyphenyl)-1,4-dihydro-4-quinolinone
• CAS: 190774-10-8
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: FNEUTVQHOSJBOC-UHFFFAOYSA-N

物化性质

• 熔点：
  240-241 °C
• 沸点：
  507.8±50.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-dimethoxy-3-(4-methoxyphenyl)-1H-quinolin-4-one 在 吡啶 、 氢溴酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 [7-Methoxy-3-(4-methoxyphenyl)-1-methyl-4-oxoquinolin-5-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  5-取代的 3-(4-甲氧基苯基)-4(1H)-喹诺酮类化合物的便捷合成路线

  摘要：

  5-取代的 3-(4-甲氧基苯基)-4(1H)-喹诺酮类 5-18 已从相应的 3-(4-甲氧基苯基)-5-三氟甲磺酸盐-4(1H)-喹诺酮类 4 经钯合成，收率良好-介导的交叉偶联反应或芳香亲核取代（SN A r ）反应。

  DOI：

  10.1055/s-2003-40845
• 作为产物：
  描述：

  N-{2-[3,3-dimethoxy-2-(4-methoxyphenyl)propionyl]-3,5-dimethoxyphenyl}acetamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.17h， 以93%的产率得到5,7-dimethoxy-3-(4-methoxyphenyl)-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

• Pharmaceutical compositions comprising 4-quinolones for treating cancers
  申请人：Laboratoire L. Lafon

  公开号：US06645983B1

  公开（公告）日：2003-11-11

  A non-cytotoxic pharmaceutical composition acting on the proliferation of clonogenic cells in malignant tumors and including an efficient amount of a compound selected among the compounds of formula (I) and (Ia).

  一种非细胞毒性药物组合物，对恶性肿瘤中克隆细胞的增殖起作用，包括在式(I)和(Ia)的化合物中选择的有效量的化合物。
• Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones
  作者：Santosh Rajput、Christopher R. Gardner、Timothy W. Failes、Greg M. Arndt、David StC. Black、Naresh Kumar

  DOI：10.1016/j.bmc.2013.11.047

  日期：2014.1

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.
• Croisy, Martine; Huel, Christiane; Bisagni, Emile, Heterocycles, 1997, vol. 45, # 4, p. 683 - 690
  作者：Croisy, Martine、Huel, Christiane、Bisagni, Emile

  DOI：——

  日期：——
• COMPOSITIONS PHARMACEUTIQUES COMPRENANT DES 4-QUINOLONES POUR LE TRAITEMENT DES CANCERS
  申请人：LABORATOIRE L. LAFON

  公开号：EP1202971A2

  公开（公告）日：2002-05-08