methyl 2-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoyl)-3-(dimethylamino)acrylate | 1333140-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoyl)-3-(dimethylamino)acrylate
• 英文别名: 2-(3-(3-chloro-2-fluorobenzyl)-2,6-difluoro benzoyl)-3-(dimethylamino) acrylate
• CAS: 1333140-90-1
• 化学式: C₂₀H₁₇ClF₃NO₃
• 分子量: 411.808
• InChiKey: OJPNNRRVVIVMKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoyl)-3-(dimethylamino)acrylate 在 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 6-(3-chloro-2-fluorobenzyl)-5-fluoro-4-oxo-1-propyl-1,4-dihydroquinoline-3-carboxylate
  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
• 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 8.0h， 生成 methyl 2-(3-(3-chloro-2-fluorobenzyl)-2,6-difluorobenzoyl)-3-(dimethylamino)acrylate
  参考文献：
  名称：

  Synthesis and biological evaluation of HQCAs with aryl or benzyl substituents on N-1 position as potential HIV-1 integrase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.07.037

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.