7-hydroxy-2-imino-2H-chromene-3-carboxylic acid benzylamide | 313497-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-hydroxy-2-imino-2H-chromene-3-carboxylic acid benzylamide
• 英文别名: N-benzyl-7-hydroxy-2-imino-2H-chromene-3-carboxamide；N-Benzyl-7-hydroxy-2-imino-2H-chromene-3-carboxamide；N-benzyl-7-hydroxy-2-iminochromene-3-carboxamide
• CAS: 313497-19-7
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: WNMOXELIHBLDDF-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  82.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxy-2-imino-2H-chromene-3-carboxylic acid benzylamide 、 1-(1-溴乙基)-2-硝基苯 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以53%的产率得到N-benzyl-2-imino-7-(1-(2-nitrophenyl)ethoxy)-2H-chromene-3-carboxamide
  参考文献：
  名称：

  Cell-Permeable Iminocoumarine-Based Fluorescent Dyes for Mitochondria

  摘要：

  A class of small molecule fluorophores, 2-iminocoumarin-3-carboxamide derivatives, has been developed by a rapid microwave-assisted process. These fluorescent probes are cell membrane permeable with low cytotoxicity and able to selectively stain organelles in living cells.

  DOI：

  10.1021/ol200908r
• 作为产物：
  描述：

  苄胺 在 哌啶 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 7-hydroxy-2-imino-2H-chromene-3-carboxylic acid benzylamide
  参考文献：
  名称：

  Cell-Permeable Iminocoumarine-Based Fluorescent Dyes for Mitochondria

  摘要：

  A class of small molecule fluorophores, 2-iminocoumarin-3-carboxamide derivatives, has been developed by a rapid microwave-assisted process. These fluorescent probes are cell membrane permeable with low cytotoxicity and able to selectively stain organelles in living cells.

  DOI：

  10.1021/ol200908r

文献信息

• Synthesis and structure–activity relationship of 2-phenyliminochromene derivatives as inhibitors for aldo–keto reductase (AKR) 1B10
  作者：Satoshi Endo、Dawei Hu、Miho Suyama、Toshiyuki Matsunaga、Kenji Sugimoto、Yuji Matsuya、Ossama El-Kabbani、Kazuo Kuwata、Akira Hara、Yukio Kitade、Naoki Toyooka

  DOI：10.1016/j.bmc.2013.08.059

  日期：2013.11

  Inhibitors of a human member (AKR1B10) of the aldo-keto reductase superfamily are regarded as promising therapeutics for the treatment of cancer. Recently, we have discovered (Z)-2(4-methoxyphenylimino)-7-hydroxy-N-(pyridin-2-yl)-2H-chromene-3-carboxamide (1) as the potent competitive inhibitor using the virtual screening approach, and proposed its 4-methoxy group on the 2-phenylimino moiety as an essential structural prerequisite for the inhibition. In this study, 18 derivatives of 1 were synthesized and their inhibitory potency against AKR1B10 evaluated. Among them, 7-hydroxy-2-(4-methoxyphenylimino)-2H-chromene-3-carboxylic acid benzylamide (5n) was the most potent inhibitor showing a K-i value of 1.3 nM. The structure-activity relationship of the derivatives indicated that the 7-hydroxyl group on the chromene ring, but not the 4-methoxy group, was absolutely required for inhibitory activity, The molecular docking of 5n in AKR1B10 and site-directed mutagenesis of the enzyme residues suggested that the hydrogen-bond interactions between the 7-hydroxyl group of 5n and the catalytic residues (Tyr49 and His111) of the enzyme, together with a pi-stacking interaction of the benzylamide moiety of 5n with Trp220, are important for the potent inhibition. (C) 2013 Elsevier Ltd. All rights reserved.
• Cell-Permeable Iminocoumarine-Based Fluorescent Dyes for Mitochondria
  作者：Diliang Guo、Tao Chen、Deju Ye、Jinyi Xu、Hualiang Jiang、Kaixian Chen、Hui Wang、Hong Liu

  DOI：10.1021/ol200908r

  日期：2011.6.3

  A class of small molecule fluorophores, 2-iminocoumarin-3-carboxamide derivatives, has been developed by a rapid microwave-assisted process. These fluorescent probes are cell membrane permeable with low cytotoxicity and able to selectively stain organelles in living cells.