methyl 6-(3-chloro-2-fluorobenzyl)-5-fluoro-4-oxo-1-pentyl-1,4-dihydroquinoline-3-carboxylate | 1333141-13-1

• 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: methyl 6-(3-chloro-2-fluorobenzyl)-5-fluoro-4-oxo-1-pentyl-1,4-dihydroquinoline-3-carboxylate
• CAS: 1333141-13-1
• 化学式: C₂₃H₂₂ClF₂NO₃
• 分子量: 433.882
• InChiKey: DJJWPKLFRNHQSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 6-(3-chloro-2-fluorobenzyl)-5-fluoro-4-oxo-1-pentyl-1,4-dihydroquinoline-3-carboxylate 在 lithium hydroxide 、 盐酸 、 水 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 6-(3-chloro-2-fluorobenzyl)-5-fluoro-4-oxo-1-pentyl-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
• 作为产物：
  描述：

  methyl 2-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoyl)-3-(pentylamino)acrylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到methyl 6-(3-chloro-2-fluorobenzyl)-5-fluoro-4-oxo-1-pentyl-1,4-dihydroquinoline-3-carboxylate
  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