8-hydroxy-2-((3-methoxyphenyl)amino)naphthalene-1,4-dione | 1446306-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-hydroxy-2-((3-methoxyphenyl)amino)naphthalene-1,4-dione
• 英文别名: 8-Hydroxy-2-(3-methoxyanilino)naphthalene-1,4-dione；8-hydroxy-2-(3-methoxyanilino)naphthalene-1,4-dione
• CAS: 1446306-89-3
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: UXRPINUQVDPAPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-羟基对萘醌 、 间氨基苯甲醚 以 乙醇 为溶剂， 以27%的产率得到8-hydroxy-2-((3-methoxyphenyl)amino)naphthalene-1,4-dione
  参考文献：
  名称：

  Anticancer activity and SAR studies of substituted 1,4-naphthoquinones

  摘要：

  In this paper, we report the structure-activity relationship studies of substituted 1,4-naphthoquinones for its anticancer properties. 1,4-Naphthoquinone, Juglone, Menadione, Plumbagin and LLL12.1 were used as lead molecules to design PD compounds. Most of the PD compounds showed improved antiproliferative activity in comparison to the lead molecule in prostate (DU-145), breast (MDA-MB-231) and colon (HT-29) cancer cell lines. PD9, PD10, PD11, PD13, PD14 and PD15 were found to be the most potent compound with an IC50 value of 1-3 mu M in all cancer cell lines. Fluorescent polarization assay was employed to study the inhibition of STAT3 dimerization by PD compounds. PD9 and PD18 were found to be potent STAT3 dimerization inhibitors. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.05.017

文献信息

• <i>In Vitro</i>Inhibition of<i>Helicobacter pylori</i>Growth by Redox Cycling Phenylaminojuglones
  作者：Julio Benites、Héctor Toledo、Felipe Salas、Angélica Guerrero、David Rios、Jaime A. Valderrama、Pedro Buc Calderon

  DOI：10.1155/2018/1618051

  日期：——

  Infection by Helicobacter pylori increases 10 times the risk of developing gastric cancer. Juglone, a natural occurring 1,4-naphthoquinone, prevents H. pylori growth by interfering with some of its critical metabolic pathways. Here, we report the design, synthesis, and in vitro evaluation of a series of juglone derivatives, namely, 2/3-phenylaminojuglones, as potential H. pylori growth inhibitors. Results

  幽门螺杆菌感染会使患胃癌的风险增加10倍。Juglone是一种天然存在的1,4-萘醌，可通过干扰幽门螺杆菌的某些关键代谢途径来阻止幽门螺杆菌的生长。在这里，我们报告设计，合成和体外评估一系列juglone衍生物，即2 / 3-苯基氨基juglones，作为潜在的幽门螺杆菌生长抑制剂。结果表明，5超过了12 phenylaminojuglones（在1.5  μ克/毫升）是1.5-2.2倍胡桃醌更活跃。有趣的是，大多数苯氨基聚醚（12个中的10个）的活性是甲硝唑（一种已知的幽门螺杆菌）的1.1-2.8倍。生长抑制剂。活性最高的化合物2-（（（3,4,5-三甲氧基苯基）氨基）-5-羟基萘-1,4-二酮7]的生长抑制晕环（HGI = 32.25 mm）明显高于juglone和甲硝唑（HGI = 14.50和11.67 mm）。该系列的结构活性关系表明，Juglone支架中氮取代基的性质和位置可能
• Anticancer activity and SAR studies of substituted 1,4-naphthoquinones
  作者：Deepak Bhasin、Somsundaram N. Chettiar、Jonathan P. Etter、May Mok、Pui-Kai Li

  DOI：10.1016/j.bmc.2013.05.017

  日期：2013.8

  In this paper, we report the structure-activity relationship studies of substituted 1,4-naphthoquinones for its anticancer properties. 1,4-Naphthoquinone, Juglone, Menadione, Plumbagin and LLL12.1 were used as lead molecules to design PD compounds. Most of the PD compounds showed improved antiproliferative activity in comparison to the lead molecule in prostate (DU-145), breast (MDA-MB-231) and colon (HT-29) cancer cell lines. PD9, PD10, PD11, PD13, PD14 and PD15 were found to be the most potent compound with an IC50 value of 1-3 mu M in all cancer cell lines. Fluorescent polarization assay was employed to study the inhibition of STAT3 dimerization by PD compounds. PD9 and PD18 were found to be potent STAT3 dimerization inhibitors. (C) 2013 Published by Elsevier Ltd.