2-(4-(((1,4-dioxo-1,4-dihydronaphthalen-2-yl)(3-methoxy-phenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)acetonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-(((1,4-dioxo-1,4-dihydronaphthalen-2-yl)(3-methoxy-phenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)acetonitrile
• 英文别名: 2-[4-[(N-(1,4-dioxonaphthalen-2-yl)-3-methoxyanilino)methyl]triazol-1-yl]acetonitrile
• 化学式: C₂₂H₁₇N₅O₃
• 分子量: 399.409
• InChiKey: UQLXAVXWPCWROP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-(((1,4-dioxo-1,4-dihydronaphthalen-2-yl)(3-methoxy-phenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)acetonitrile 、 水杨醛 在 三乙胺 作用下， 反应 1.0h， 以77%的产率得到2-(((1-(2-imino-2H-chromen-3-yl)-1H-1,2,3-triazol-4-yl)-methyl)(3-methoxyphenyl)amino)naphthalene-1,4-dione
  参考文献：
  名称：

  Sequential synthesis of amino-1,4-naphthoquinone-appended triazoles and triazole-chromene hybrids and their antimycobacterial evaluation

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.08.009
• 作为产物：
  描述：

  azidoacetonitrile 、 2-((3-methoxyphenyl)(prop-2-ynyl)amino)naphthalene-1,4-dione 在 copper(l) iodide 、 三乙胺 作用下， 以 水 为溶剂， 反应 0.02h， 生成 2-(4-(((1,4-dioxo-1,4-dihydronaphthalen-2-yl)(3-methoxy-phenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)acetonitrile
  参考文献：
  名称：

  Sequential synthesis of amino-1,4-naphthoquinone-appended triazoles and triazole-chromene hybrids and their antimycobacterial evaluation

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.08.009

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.