2-(prop-2-ynyl(p-tolyl)amino)naphthalene-1,4-dione | 1445727-17-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(prop-2-ynyl(p-tolyl)amino)naphthalene-1,4-dione
• 英文别名: 2-(4-methyl-N-prop-2-ynylanilino)naphthalene-1,4-dione
• CAS: 1445727-17-2
• 化学式: C₂₀H₁₅NO₂
• 分子量: 301.345
• InChiKey: ZBHKDFPLMZRUBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(prop-2-ynyl(p-tolyl)amino)naphthalene-1,4-dione 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以71%的产率得到1-p-tolyl-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：

  1,4-萘醌 在 copper(II) acetate monohydrate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 2-(prop-2-ynyl(p-tolyl)amino)naphthalene-1,4-dione
  参考文献：
  名称：

  探戈需要两个人：合成含有两个具有潜在抗肿瘤活性的氧化还原活性中心的细胞毒性醌

  摘要：

  我们报告了通过点击化学合成 47 种新的基于醌的衍生物及其随后对癌细胞系和对照 L929 鼠成纤维细胞系的评估。这些化合物结合了两个氧化还原中心，例如邻-醌/对-醌或醌/硒与 1,2,3-三唑核。其中几种化合物在癌细胞系中的IC 50值低于 0.5 μM，在对照细胞系 L929 中的细胞毒性显着降低，选择性指数良好。因此，我们的研究证实了使用完整且非常多样化的醌类化合物，这些化合物具有针对某些癌细胞系的潜在应用。

  DOI：

  10.1039/d1md00168j

文献信息

• Sequential synthesis of amino-1,4-naphthoquinone-appended triazoles and triazole-chromene hybrids and their antimycobacterial evaluation
  作者：Balasubramanian Devi Bala、Sivasubramanian Muthusaravanan、Tan Soo Choon、Mohamed Ashraf Ali、Subbu Perumal

  DOI：10.1016/j.ejmech.2014.08.009

  日期：2014.10

  A general method for the synthesis of a library of hitherto unreported amino-1,4-naphthoquinone-appended triazoles was accomplished via a sequential three-component reaction of substituted N-propargylaminonaphthoquinones with variously substituted alkyl bromides/2-bromonaphthalene-1,4-dione and sodium azide in the presence of Et3N/CuI in water. Aminonaphthoquinone-appended iminochromene-triazole hybrid heterocycles were also synthesized from the amino-1,4-naphthoquinone-appended-1,2,3-triazolylacetonitriles. All the triazole hybrids were screened for their in vitro activity against Mycobacterium tuberculosis H(37)Rv (MTB). Among the triazoles, 2-(((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)(4-(trifluoromethyl)phenyl)amino)naphthalene-1,4-dione (7d) emerged as the most active one with IC50 = 1.87 mu M, being more potent than the anti-TB drugs, cycloserine (6 times), pyrimethamine (20 times) and equipotent as the drug ethambutol (IC50 < 1.56 mu M). (C) 2014 Elsevier Masson SAS. All rights reserved.