ethyl 1-ethyl-7-[4-(2-hydroxypropan-2-yl)-1H-1,2,3-triazol-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylate

• 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: ethyl 1-ethyl-7-[4-(2-hydroxypropan-2-yl)-1H-1,2,3-triazol-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylate
• 英文别名: Ethyl 1-ethyl-7-[4-(2-hydroxypropan-2-yl)triazol-1-yl]-4-oxoquinoline-3-carboxylate；ethyl 1-ethyl-7-[4-(2-hydroxypropan-2-yl)triazol-1-yl]-4-oxoquinoline-3-carboxylate
• 化学式: C₁₉H₂₂N₄O₄
• 分子量: 370.408
• InChiKey: AXCRFLACLOTCAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  97.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ethyl 7-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 盐酸 、 copper(ll) sulfate pentahydrate 、 铁粉 、 氯化铵 、 维生素 C 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.75h， 生成 ethyl 1-ethyl-7-[4-(2-hydroxypropan-2-yl)-1H-1,2,3-triazol-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  1,2,3-Triazolyl-4-oxoquinolines: A feasible beginning for promising chemical structures to inhibit oseltamivir-resistant influenza A and B viruses

  摘要：

  We described the synthesis of a new congener series of 1,2,3-triazolyl-4-oxoquinolines and evaluated their ability to inhibit oseltamivir (OST)-resistant influenza strains. Oxoquinoline derivative 1i was the most potent compound within this series, inhibiting 94% of wild-type (WT) influenza neuraminidase (NA) activity. Compound 1i inhibited influenza virus replication with an EC50 of 0.2 mu M with less cytotoxicity than OST, and also inhibited different OST-resistant NAs. These results suggest that 1,2,3-triazolyl-4-oxoquinolines represent promising lead molecules for further anti-influenza drug design. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2015.11.028

文献信息

• 1,2,3-Triazolyl-4-oxoquinolines: A feasible beginning for promising chemical structures to inhibit oseltamivir-resistant influenza A and B viruses
  作者：Fernanda da C.S. Boechat、Carolina Q. Sacramento、Anna C. Cunha、Fernanda S. Sagrillo、Christiane M. Nogueira、Natalia Fintelman-Rodrigues、Osvaldo Santos-Filho、Cecília S. Riscado、Luana da S.M. Forezi、Letícia V. Faro、Leonardo Brozeguini、Isakelly P. Marques、Vitor F. Ferreira、Thiago Moreno L. Souza、Maria Cecília B.V. de Souza

  DOI：10.1016/j.bmc.2015.11.028

  日期：2015.12

  We described the synthesis of a new congener series of 1,2,3-triazolyl-4-oxoquinolines and evaluated their ability to inhibit oseltamivir (OST)-resistant influenza strains. Oxoquinoline derivative 1i was the most potent compound within this series, inhibiting 94% of wild-type (WT) influenza neuraminidase (NA) activity. Compound 1i inhibited influenza virus replication with an EC50 of 0.2 mu M with less cytotoxicity than OST, and also inhibited different OST-resistant NAs. These results suggest that 1,2,3-triazolyl-4-oxoquinolines represent promising lead molecules for further anti-influenza drug design. Published by Elsevier Ltd.