4-(hydroxyamino)-N-methyl-2-oxo-6-p-tolyl-2H-pyran-3-carboxamide | 1512807-61-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(hydroxyamino)-N-methyl-2-oxo-6-p-tolyl-2H-pyran-3-carboxamide
• 英文别名: 4-(hydroxyamino)-N-methyl-6-(4-methylphenyl)-2-oxopyran-3-carboxamide
• CAS: 1512807-61-2
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: IMLIXTROALKNCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(hydroxyamino)-N-methyl-2-oxo-6-p-tolyl-2H-pyran-3-carboxamide 在 sodium hydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-(methylamino)-6-(p-tolyl)-4H-pyrano[4,3-c]isoxazol-4-one
  参考文献：
  名称：

  Intramolecular cyclization to fused pyranoisoxazoles and molecular packing motifs identification through X-ray structural studies

  摘要：

  DOI：

  10.1016/j.jics.2021.100135
• 作为产物：
  描述：

  N-methyl-4-(methylthio)-2-oxo-6-p-tolyl-2H-pyran-3-carboxamide 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以82%的产率得到4-(hydroxyamino)-N-methyl-2-oxo-6-p-tolyl-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.
• Intramolecular cyclization to fused pyranoisoxazoles and molecular packing motifs identification through X-ray structural studies
  作者：Sarika Verma、Ashoke Sharon

  DOI：10.1016/j.jics.2021.100135

  日期：2021.9