N-(4-fluorobenzyl)-3-hydroxy-2-oxoquinoline-4-carboxamide | 1383627-91-5

• 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: N-(4-fluorobenzyl)-3-hydroxy-2-oxoquinoline-4-carboxamide
• 英文别名: N-[(4-fluorophenyl)methyl]-3-hydroxy-2-oxo-1H-quinoline-4-carboxamide
• CAS: 1383627-91-5
• 化学式: C₁₇H₁₃FN₂O₃
• 分子量: 312.3
• InChiKey: GKJSKQLCMNEMBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 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：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-fluorobenzyl)-3-hydroxy-2-oxoquinoline-4-carboxamide 在 magnesium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以89%的产率得到
  参考文献：
  名称：

  Development of a series of 3-hydroxyquinolin-2(1H)-ones as selective inhibitors of HIV-1 reverse transcriptase associated RNase H activity

  摘要：

  We report herein the synthesis of a series of 3-hydroxyquinolin-2(1H)-one derivatives. Esters and amide groups were introduced at position 4 of the basis scaffold and some modulations of the benzenic moiety were performed. Most compounds presented selective inhibitory properties in the 10-20 mu M range against HIV-1 reverse transcriptase associated ribonuclease H activity, without affecting the integrase and reverse transcriptase DNA polymerase activities. Unfortunately all tested compounds exhibited high cellular cytotoxicity in cell culture which limited their applications as antiviral agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.096
• 作为产物：
  描述：

  3-Hydroxy-3-(ethoxycarbonyl-diazomethyl)-oxindol 在 盐酸 、 氯化亚砜 、 水 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 16.5h， 生成 N-(4-fluorobenzyl)-3-hydroxy-2-oxoquinoline-4-carboxamide
  参考文献：
  名称：

  Development of a series of 3-hydroxyquinolin-2(1H)-ones as selective inhibitors of HIV-1 reverse transcriptase associated RNase H activity

  摘要：

  We report herein the synthesis of a series of 3-hydroxyquinolin-2(1H)-one derivatives. Esters and amide groups were introduced at position 4 of the basis scaffold and some modulations of the benzenic moiety were performed. Most compounds presented selective inhibitory properties in the 10-20 mu M range against HIV-1 reverse transcriptase associated ribonuclease H activity, without affecting the integrase and reverse transcriptase DNA polymerase activities. Unfortunately all tested compounds exhibited high cellular cytotoxicity in cell culture which limited their applications as antiviral agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.096

文献信息

• Development of a series of 3-hydroxyquinolin-2(1H)-ones as selective inhibitors of HIV-1 reverse transcriptase associated RNase H activity
  作者：Virginie Suchaud、Fabrice Bailly、Cédric Lion、Enzo Tramontano、Francesca Esposito、Angela Corona、Frauke Christ、Zeger Debyser、Philippe Cotelle

  DOI：10.1016/j.bmcl.2012.04.096

  日期：2012.6

  We report herein the synthesis of a series of 3-hydroxyquinolin-2(1H)-one derivatives. Esters and amide groups were introduced at position 4 of the basis scaffold and some modulations of the benzenic moiety were performed. Most compounds presented selective inhibitory properties in the 10-20 mu M range against HIV-1 reverse transcriptase associated ribonuclease H activity, without affecting the integrase and reverse transcriptase DNA polymerase activities. Unfortunately all tested compounds exhibited high cellular cytotoxicity in cell culture which limited their applications as antiviral agents. (C) 2012 Elsevier Ltd. All rights reserved.