2-((4-methoxyphenyl)amino)-3-methylnaphthalene-1,4-dione | 70150-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((4-methoxyphenyl)amino)-3-methylnaphthalene-1,4-dione
• 英文别名: 2-(4-methoxyanilino)-3-methylnaphthalene-1,4-dione
• CAS: 70150-74-2
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: WPNNXXUKCCQBMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲萘醌 、 甲氧苯胺 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 以21 %的产率得到2-((4-methoxyphenyl)amino)-3-methylnaphthalene-1,4-dione
  参考文献：
  名称：

  含有 3-N-取代芳香环和哌嗪环的新型维生素 K3 类似物，对 HeLa、U87 MG 和 MCF-7 细胞具有选择性体外抗癌活性

  摘要：

  在这项研究中，首先，通过维生素 K3（2-甲基-1,4-萘醌，也称为甲萘醌）与一些芳香族和杂环取代的亲核试剂（如 2,4-二甲氧基苯胺）的反应合成了新型维生素 K3 类似物，室温下，乙醇/Na 2 CO 3中的 4-甲氧基苯胺、4-苄基哌啶和 1-(2-氨基乙基)哌嗪，以及氯仿/三乙胺 (TEA) 中的 1-(二苯基甲基)哌嗪。它们的结构通过傅立叶变换红外光谱 (FT-IR)、1 H 核磁共振 ( 1H NMR), 附加质子测试核磁共振 (APT-NMR) 和质谱 (MS)。其次，通过 MTT 法研究了维生素 K3 类似物对三种癌细胞系（HeLa、U87 MG 和 MCF-7）的体外细胞毒性作用，以评估其抗癌活性，并通过人胚肾细胞系（HEK-293）检查他们的癌细胞选择性。其中一种化合物，即 2-((2,4-二甲氧基苯基)氨基)-3-甲基萘-1,4-二酮 (5)，被发现可以选择性地抑制 HeLa

  DOI：

  10.1007/s00044-023-03019-9

文献信息

• Reactions of iminodimagnesium reagents with 1,4-quinones: Their structural factors governing the modes of reactions
  作者：Koji Matsuo、Ryuji Shiraki、Masao Okubo

  DOI：10.1002/poc.610071008

  日期：1994.10

  Reactions of benzo-, naphtho- and anthraquinone derivatives (unsubstituted and substituted) with aryliminodimagnesium [ArN(MgBr)2] and aryloxymagnesium of a weak electron-donating ability were studied. In addition to the reduction products (quinhydrones and hydroquinones), nuclear substitution and condensation

  研究了苯醌，萘和蒽醌衍生物（未取代和取代）与电子给体能力弱的芳基二镁[ArN（MgBr）2 ]和芳氧基镁的反应。除还原产物（对苯二酚和对苯二酚）外，核取代和缩合
• INHIBITORS OF THE MITF MOLECULAR PATHWAY
  申请人：THE GENERAL HOSPITAL CORPORATION

  公开号：US20160130222A1

  公开（公告）日：2016-05-12

  Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.

  本文提供的是公式（IV）的化合物及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及其含有的药物组合物可用作MITF抑制剂、MITF通路抑制剂以及治疗癌症的药物。
• 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.
• KALLMEYER H.-J., ARCH. PHARM., 1979, 312, NO 3, 230-239
  作者：KALLMEYER H.-J.

  DOI：——

  日期：——
• BIOMARKERS PREDICTIVE OF CANCER CELL RESPONSE TO ML329 OR A DERIVATIVE THEREOF
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US20220128562A1

  公开（公告）日：2022-04-28

  The present invention is based in part on the identification of biomarkers, including NQO1, NRF2 and KEAP1, predictive of cancer cell responsiveness to treatment with ML 329 or a derivative thereof.