Ethyl 6-azido-1-ethyl-4-oxoquinoline-3-carboxylate | 1096162-75-2

• 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 6-azido-1-ethyl-4-oxoquinoline-3-carboxylate
• CAS: 1096162-75-2
• 化学式: C₁₄H₁₄N₄O₃
• 分子量: 286.29
• InChiKey: DZEGTZXKBVUNJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 6-azido-1-ethyl-4-oxoquinoline-3-carboxylate 、 炔环己醇 在 copper(ll) sulfate pentahydrate 、 维生素 C 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以83%的产率得到ethyl 1-ethyl-6-[4-(1-hydroxycyclohexyl)-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
• 作为产物：
  描述：

  ethyl 6-amino-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 反应 0.75h， 生成 Ethyl 6-azido-1-ethyl-4-oxoquinoline-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

• Synthesis of porphyrin–quinolone conjugates
  作者：Fernanda da C. Santos、Anna C. Cunha、Maria Cecília B.V. de Souza、Augusto C. Tomé、Maria G.P.M.S. Neves、Vitor F. Ferreira、José A.S. Cavaleiro

  DOI：10.1016/j.tetlet.2008.10.024

  日期：2008.12

  meso-Tetrakis(pentafluorophenyl)porphyrin reacts with propargyl alcohol to afford porphyrins substituted with one, two, three or four prop-2-yn-1-yloxy groups in the 4-position of the meso-aryl groups. These new porphyrin derivatives react with a 6-azidoquinolone under 'click-chemistry' conditions to give porphyrin-quinolone conjugates linked by 1,2,3-triazole units. (C) 2008 Elsevier Ltd. All rights reserved.