N-(m-tolyl)-2-(4-{[N-(2,2,4-trimethyl-7-phenoxy-1,2-dihydroquinolin-6-yl)methanesulfonamido]methyl}-1H-1,2,3-triazol-1-yl)acetamide | 1601552-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(m-tolyl)-2-(4-{[N-(2,2,4-trimethyl-7-phenoxy-1,2-dihydroquinolin-6-yl)methanesulfonamido]methyl}-1H-1,2,3-triazol-1-yl)acetamide
• 英文别名: N-(3-methylphenyl)-2-[4-[[methylsulfonyl-(2,2,4-trimethyl-7-phenoxy-1H-quinolin-6-yl)amino]methyl]triazol-1-yl]acetamide
• CAS: 1601552-71-9
• 化学式: C₃₁H₃₄N₆O₄S
• 分子量: 586.715
• InChiKey: ONRKPHBGENLQCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  尼美舒利 在 盐酸 、 tin 、 copper(ll) sulfate pentahydrate 、 ammonium cerium (IV) nitrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 26.0h， 生成 N-(m-tolyl)-2-(4-{[N-(2,2,4-trimethyl-7-phenoxy-1,2-dihydroquinolin-6-yl)methanesulfonamido]methyl}-1H-1,2,3-triazol-1-yl)acetamide
  参考文献：
  名称：

  Synthesis of 2,2,4-trimethyl-1,2-dihydroquinolinyl substituted 1,2,3-triazole derivatives: Their evaluation as potential PDE 4B inhibitors possessing cytotoxic properties against cancer cells

  摘要：

  The 2,2,4-trimethyl-1,2-dihydroquinolinyl substituted 1,2,3-triazole derivatives were designed as potential inhibitors of PDE4B. These compounds were synthesized via a multi-step sequence consisting of copper-catalyzed azide-alkyne cycloaddition (CuAAC) as a key step in aqueous media. The required alkynes were prepared from nimesulide via N-propargylation and then nitro group reduction followed by a CAN mediated modified Skraup reaction of the resulting amine. All the synthesized compounds showed PDE4B inhibitory properties in vitro at 30 mu M with two compounds showing >50% inhibition that were supported by the in silico docking results of these compounds at the active site of PDE4B. Three of these PDE4 inhibitors showed promising cytotoxic properties against A549 human lung cancer cells in vitro with IC50 similar to 8-9 mu M. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.12.002

文献信息

• Synthesis of 2,2,4-trimethyl-1,2-dihydroquinolinyl substituted 1,2,3-triazole derivatives: Their evaluation as potential PDE 4B inhibitors possessing cytotoxic properties against cancer cells
  作者：K.S.S. Praveena、Shylaprasad Durgadas、N. Suresh Babu、Surekha Akkenapally、C. Ganesh Kumar、Girdhar Singh Deora、N.Y.S. Murthy、Khagga Mukkanti、Sarbani Pal

  DOI：10.1016/j.bioorg.2013.12.002

  日期：2014.4

  The 2,2,4-trimethyl-1,2-dihydroquinolinyl substituted 1,2,3-triazole derivatives were designed as potential inhibitors of PDE4B. These compounds were synthesized via a multi-step sequence consisting of copper-catalyzed azide-alkyne cycloaddition (CuAAC) as a key step in aqueous media. The required alkynes were prepared from nimesulide via N-propargylation and then nitro group reduction followed by a CAN mediated modified Skraup reaction of the resulting amine. All the synthesized compounds showed PDE4B inhibitory properties in vitro at 30 mu M with two compounds showing >50% inhibition that were supported by the in silico docking results of these compounds at the active site of PDE4B. Three of these PDE4 inhibitors showed promising cytotoxic properties against A549 human lung cancer cells in vitro with IC50 similar to 8-9 mu M. (C) 2013 Elsevier Inc. All rights reserved.