(S)-6-(3-chloro-2-fluorobenzyl)-5-fluoro-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 1447671-99-9

• 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: (S)-6-(3-chloro-2-fluorobenzyl)-5-fluoro-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 6-[(3-chloro-2-fluorophenyl)methyl]-5-fluoro-1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 1447671-99-9
• 化学式: C₂₂H₂₀ClF₂NO₄
• 分子量: 435.855
• InChiKey: VCXKKVAXPWCYEQ-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl (S)-6-(3-chloro-2-fluorobenzyl)-5-fluoro-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以70%的产率得到(S)-6-(3-chloro-2-fluorobenzyl)-5-fluoro-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-fluoroquinolone-3-carboxylic acids as potential HIV-1 integrase inhibitors

  摘要：

  A series of new quinolone-3-carboxylic acids as HIV-1 integrase inhibitors featuring a fluorine atom at C-5 position were synthesized and evaluated for their antiviral activity in C8166 cell culture. These newly synthesized compounds showed anti-HIV activity against wild-type virus with an EC50 value ranging from 29.85 to 0.032 mu M. The most active compound 4e exhibited activity against wild-type virus and the mutant virus A17 with an EC50 value of 0.032 and 0.082 mu M, respectively. Preliminary structure-activity relationship of these 5-fluoroquinolone-3-carboxylic acids was also investigated.

  DOI：

  10.3109/14756366.2012.668540

文献信息

• Synthesis and biological evaluation of 5-fluoroquinolone-3-carboxylic acids as potential HIV-1 integrase inhibitors
  作者：Qiu-Qin He、Xuan Zhang、Liu-Meng Yang、Yong-Tang Zheng、Fener Chen

  DOI：10.3109/14756366.2012.668540

  日期：2013.8.1

  A series of new quinolone-3-carboxylic acids as HIV-1 integrase inhibitors featuring a fluorine atom at C-5 position were synthesized and evaluated for their antiviral activity in C8166 cell culture. These newly synthesized compounds showed anti-HIV activity against wild-type virus with an EC50 value ranging from 29.85 to 0.032 mu M. The most active compound 4e exhibited activity against wild-type virus and the mutant virus A17 with an EC50 value of 0.032 and 0.082 mu M, respectively. Preliminary structure-activity relationship of these 5-fluoroquinolone-3-carboxylic acids was also investigated.