2-((2,4-dichlorophenyl)amino)naphthalene-1,4-dione | 94429-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((2,4-dichlorophenyl)amino)naphthalene-1,4-dione
• 英文别名: 2-(2,4-dichloro-anilino)-[1,4]naphthoquinone；2-(2,4-Dichlor-anilino)-[1,4]naphthochinon；2-(2,4-Dichloroanilino)naphthalene-1,4-dione
• CAS: 94429-14-8
• 化学式: C₁₆H₉Cl₂NO₂
• 分子量: 318.159
• InChiKey: IWECZBRIWCRGJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((2,4-dichlorophenyl)amino)naphthalene-1,4-dione 在 四丁基溴化铵 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 2.5h， 生成 1-(2,4-dichlorophenyl)-1,2-dihydrobenzo[g]quinoline-5,10-dione
  参考文献：
  名称：

  An expedient synthesis of 1,2-dihydrobenzo[g]quinoline-5,10-diones via copper(II) triflate-catalyzed intramolecular cyclization of N-propargylaminonaphthoquinones

  摘要：

  An expedient synthesis of a series of 1,2-dihydrobenzo[g]quinoline-5,10-diones in good yields has been accomplished via three-component one pot sequential reactions of 2-hydroxynaphthalene-1,4-dione, substituted anilines and propargyl as well as 3-ethylpropargyl bromides furnishing N-propargylaminonaphthoquinones, and their concomitant copper(II) triflate-catalyzed intramolecular 6-endo-dig cyclization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.125
• 作为产物：
  描述：

  2,4-二氯苯胺 在 potassium carbonate 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 2-((2,4-dichlorophenyl)amino)naphthalene-1,4-dione
  参考文献：
  名称：

  Novel 2-Amino-1,4-Naphthoquinone Derivatives Induce A549 Cell Death through Autophagy

  摘要：

  合成了一系列可用作抗癌剂的 1,4-萘醌衍生物，并通过 X 射线衍射证实了化合物 5a 的晶体结构。化合物 5i 对 A549 细胞株具有显著的细胞毒性，IC50 为 6.15 μM。令人惊讶的是，在接下来的初步生物学实验中，我们发现化合物 5i 通过促进表皮生长因子受体（EGFR）的循环和信号转导，诱导了 A549 细胞的自噬，从而激活了 EGFR 信号通路。分子对接还确定了化合物 5i 与表皮生长因子受体酪氨酸激酶（PDB ID：1M17）的潜在结合模式。我们的研究为进一步研究和开发新型强效抗癌药物铺平了道路。

  DOI：

  10.3390/molecules28083289

文献信息

• 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。
• Manganese(III) Acetate Initiated Oxidative Free Radical Reaction between 2-Anilino-1,4-naphthoquinones and Diethyl Malonate
  作者：Che-Ping Chuang、Sheow-Fong Wang

  DOI：10.1002/jccs.199700042

  日期：1997.6

  AbstractA free radical reaction between 2‐anilino‐1,4‐naphthoquinones and diethyl malonate initiated by manganese (III) acetate is described. This reaction provides a novel method for the synthesis of 5,6,11,12‐tetra‐hydro‐6,11‐dioxo‐benzo[b]acridines. With a meta substituent on the anilino group, this reaction shows poor to high regioselectivity depending on the steric effect of the substituents on the anilino group and malonate.
• 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.
• US9745261B2
  申请人：——

  公开号：US9745261B2

  公开（公告）日：2017-08-29
• [EN] INHIBITORS OF THE MITF MOLECULAR PATHWAY<br/>[FR] INHIBITEURS DE LA VOIE MOLÉCULAIRE MITF
  申请人：GEN HOSPITAL CORP

  公开号：WO2014201016A2

  公开（公告）日：2014-12-18

  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.