(S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 1333141-31-3

• 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-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 6-[(3-Chloro-2-fluoro-phenyl)methyl]-5-hydroxy-1-[(1S)-1-(hydroxymethyl)-2-methyl-propyl]-4-oxo-quinoline-3-carboxylic acid；6-[(3-chloro-2-fluorophenyl)methyl]-5-hydroxy-1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 1333141-31-3
• 化学式: C₂₂H₂₁ClFNO₅
• 分子量: 433.864
• InChiKey: KWMYEDHNWNCEQC-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 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：
  98.1
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,6-二氟苯甲酸 在 N-碘代丁二酰亚胺 、 三甲基氯硅烷 、 氯化亚砜 、 硫酸 、 三溴化硼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1,2-二溴乙烷 、 N,N'-羰基二咪唑 、 lithium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 (S)-6-(3-chloro-2-fluorobenzyl)-5-hydroxy-1-(1-hydroxy-3-methylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Structural modifications of quinolone-3-carboxylic acids with anti-HIV activity

  摘要：

  A series of new quinolone-3-carboxylic acids featuring a hydroxyl group at C-5 position were synthesized and evaluated for their in vitro activity against HIV in C8166 cell culture. All the compounds showed anti-HIV-1 activity with low micromolar to submicromolar EC(50) values. The most active compound 2k exhibited activity against wild-type HIV-1 with an EC(50) value of 0.13 mu M. Preliminary structure-activity relationship of the newly synthesized quinolone analogues was also investigated. Further docking study revealed that the anti-HIV activity of these compounds might involve a two-metal chelating mechanism. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.020

文献信息

• Structural modifications of quinolone-3-carboxylic acids with anti-HIV activity
  作者：Qiu-Qin He、Shuang-Xi Gu、Jia Liu、Hai-Qiu Wu、Xuan Zhang、Liu-Meng Yang、Yong-Tang Zheng、Fen-Er Chen

  DOI：10.1016/j.bmc.2011.06.020

  日期：2011.8

  A series of new quinolone-3-carboxylic acids featuring a hydroxyl group at C-5 position were synthesized and evaluated for their in vitro activity against HIV in C8166 cell culture. All the compounds showed anti-HIV-1 activity with low micromolar to submicromolar EC(50) values. The most active compound 2k exhibited activity against wild-type HIV-1 with an EC(50) value of 0.13 mu M. Preliminary structure-activity relationship of the newly synthesized quinolone analogues was also investigated. Further docking study revealed that the anti-HIV activity of these compounds might involve a two-metal chelating mechanism. (C) 2011 Elsevier Ltd. All rights reserved.