2-((3-methoxyphenyl)(prop-2-ynyl)amino)naphthalene-1,4-dione | 1445727-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((3-methoxyphenyl)(prop-2-ynyl)amino)naphthalene-1,4-dione
• CAS: 1445727-23-0
• 化学式: C₂₀H₁₅NO₃
• 分子量: 317.344
• InChiKey: BKBWUYCKOWHBDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-((3-methoxyphenyl)(prop-2-ynyl)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-(3-methoxyphenyl)-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-羟基-1,4-萘醌 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 20.0~100.0 ℃ 、100.0 kPa 条件下， 反应 1.05h， 生成 2-((3-methoxyphenyl)(prop-2-ynyl)amino)naphthalene-1,4-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

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.