methyl 3-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorophenyl)-3-oxopropanoate | 1333140-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorophenyl)-3-oxopropanoate
• CAS: 1333140-89-8
• 化学式: C₁₇H₁₂ClF₃O₃
• 分子量: 356.729
• InChiKey: JMNQXBDSNCULOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorophenyl)-3-oxopropanoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (S)-6-(3-chloro-2-fluorobenzyl)-1-(1-hydroxy-3-methylbutan-2-yl)-5-methoxy-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
• 作为产物：
  描述：

  methyl 3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoate 在 N,N'-羰基二咪唑 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 methyl 3-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorophenyl)-3-oxopropanoate
  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

• Synthesis and biological evaluation of HQCAs with aryl or benzyl substituents on N-1 position as potential HIV-1 integrase inhibitors
  作者：Qiu-Qin He、Xuan Zhang、Hai-Qiu Wu、Shuang-Xi Gu、Xiao-Dong Ma、Liu-Meng Yang、Yong-Tang Zheng、Fen-Er Chen

  DOI：10.1016/j.bmc.2011.07.037

  日期：2011.9

  A series of new 5-hydroxylquinolone-3-carboxylic acids (HQCAs) with various aryl or benzyl substituents on N-1 position were synthesized and evaluated for their anti-HIV activity in C8166 cell culture. Most of the target compounds displayed activity against wide-type HIV-1 in the low micromolar range in infected C8166 cells. The most active compound 5g exhibited activity against wild-type HIV-1 and HIV-1 mutant virus A17 with an EC50 value of 3.17 and 17.88 mu M, respectively. The biological results and the docking study revealed that the substitution pattern on N-1 position of the quinolone core might contribute to physicochemical properties of HQCAs and resulted in great influence on their antiviral potency. (C) 2011 Elsevier Ltd. All rights reserved.