N-benzyl-4-(hydroxyamino)-6-(4-methoxyphenyl)-2-oxo-2H-pyran-3-carboxamide | 1512807-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-benzyl-4-(hydroxyamino)-6-(4-methoxyphenyl)-2-oxo-2H-pyran-3-carboxamide
• 英文别名: N-benzyl-4-(hydroxyamino)-6-(4-methoxyphenyl)-2-oxopyran-3-carboxamide
• CAS: 1512807-99-6
• 化学式: C₂₀H₁₈N₂O₅
• 分子量: 366.373
• InChiKey: ZVCCPFBEESJILL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-(p-methoxyphenyl)-4-methylthio-2-oxo-2H-pyran-3-carboxylic acid 在 盐酸羟胺 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-benzyl-4-(hydroxyamino)-6-(4-methoxyphenyl)-2-oxo-2H-pyran-3-carboxamide
  参考文献：
  名称：

  Synthesis and Anti-HCV Activity of 4-Hydroxyamino α-Pyranone Carboxamide Analogues

  摘要：

  High genetic variability in hepatitis C virus (HCV), emergence of drug resistant viruses and side effects demand the requirement for development of new scaffolds to show an alternate mechanism. Herein, we report discovery of new scaffold I based on 4-hydroxyamino alpha-pyranone carboxamide as promising anti-HCV agents. A comprehensive structure activity relationship (SAR) was explored with several newly synthesized compounds. In all promising compounds (17-19, 21-22, 24-25, and 49) with EC50 ranging 0.15 to 0.40 mu M, the aryl group at C-6 position of alpha-pyranone were unsubstituted. In particular, 25 demonstrated potential anti-HCV activity with EC50 of 0.18 mu M in cell based HCV replicon system with lower cytotoxicity (CC50 > 20 mu M) and provided a new scaffold for anti-HCV drug development. Further investigations, including biochemical characterization, are yet to be performed to elucidate its possible mode of action.

  DOI：

  10.1021/ml400432f

文献信息

• [EN] NOVEL PYRANONE CARBOXAMIDE DERIVATIVE AND USE THEREOF AS ANTI-HEPATITIS C VIRUS AGENT<br/>[FR] NOUVEAU DÉRIVÉ DE PYRANONE-CARBOXAMIDE ET UTILISATION CORRESPONDANTE COMME AGENT ANTI-VIRUS D'HÉPATITE C
  申请人：UNIV KAGOSHIMA

  公开号：WO2015008779A1

  公开（公告）日：2015-01-22

  　本発明は、下記式（Ｉ）：（式中、Ａｒは置換又は無置換の芳香族基であり、Ｒは置換又は無置換の炭化水素基、又は置換又は無置換の複素環基であり、ｎは０～３の整数である。） で示される化合物、その塩又はそれらの溶媒和物、及び前記化合物を含有する抗ＨＣＶ薬に関する。
• Synthesis and Anti-HCV Activity of 4-Hydroxyamino α-Pyranone Carboxamide Analogues
  作者：Ananda Kumar Konreddy、Massaki Toyama、Wataru Ito、Chandralata Bal、Masanori Baba、Ashoke Sharon

  DOI：10.1021/ml400432f

  日期：2014.3.13

  High genetic variability in hepatitis C virus (HCV), emergence of drug resistant viruses and side effects demand the requirement for development of new scaffolds to show an alternate mechanism. Herein, we report discovery of new scaffold I based on 4-hydroxyamino alpha-pyranone carboxamide as promising anti-HCV agents. A comprehensive structure activity relationship (SAR) was explored with several newly synthesized compounds. In all promising compounds (17-19, 21-22, 24-25, and 49) with EC50 ranging 0.15 to 0.40 mu M, the aryl group at C-6 position of alpha-pyranone were unsubstituted. In particular, 25 demonstrated potential anti-HCV activity with EC50 of 0.18 mu M in cell based HCV replicon system with lower cytotoxicity (CC50 > 20 mu M) and provided a new scaffold for anti-HCV drug development. Further investigations, including biochemical characterization, are yet to be performed to elucidate its possible mode of action.