methyl 4-((3-acetyl-4-oxoquinolin-1(4H)-yl)methyl)benzoate

• 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 4-((3-acetyl-4-oxoquinolin-1(4H)-yl)methyl)benzoate
• 英文别名: Methyl 4-[(3-acetyl-4-oxoquinolin-1-yl)methyl]benzoate；methyl 4-[(3-acetyl-4-oxoquinolin-1-yl)methyl]benzoate
• 化学式: C₂₀H₁₇NO₄
• 分子量: 335.359
• InChiKey: AILTWVRZYSRCTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-((3-acetyl-4-oxoquinolin-1(4H)-yl)methyl)benzoate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以97%的产率得到4-((3-acetyl-4-oxoquinolin-1(4H)-yl)methyl)benzoic acid
  参考文献：
  名称：

  Discovery of N-aryl-naphthylamines as in vitro inhibitors of the interaction between HIV integrase and the cofactor LEDGF/p75

  摘要：

  A series of N-aryl-naphthylamines, exemplified by the structures 11-16, were chosen for an in-house library screening to assay their ability to disrupt the interaction between the LEDGF cofactor and the HIV integrase. Structure modification led also to design and synthesize new compounds 17a-f. Compounds 11e,h,k,n, 13b, and 14 showed good activity in AlphaScreen assay. The most active compound lie (IC50 = 2.5 mu M) was selected for molecular modeling studies and showed a binding mode similar to the one of the known LEDGIN 8. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.036
• 作为产物：
  描述：

  4-溴甲基苯甲酸甲酯 、 3-acetylquinolin-4(1H)-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以84%的产率得到methyl 4-((3-acetyl-4-oxoquinolin-1(4H)-yl)methyl)benzoate
  参考文献：
  名称：

  Discovery of N-aryl-naphthylamines as in vitro inhibitors of the interaction between HIV integrase and the cofactor LEDGF/p75

  摘要：

  A series of N-aryl-naphthylamines, exemplified by the structures 11-16, were chosen for an in-house library screening to assay their ability to disrupt the interaction between the LEDGF cofactor and the HIV integrase. Structure modification led also to design and synthesize new compounds 17a-f. Compounds 11e,h,k,n, 13b, and 14 showed good activity in AlphaScreen assay. The most active compound lie (IC50 = 2.5 mu M) was selected for molecular modeling studies and showed a binding mode similar to the one of the known LEDGIN 8. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.036

文献信息

• Discovery of N-aryl-naphthylamines as in vitro inhibitors of the interaction between HIV integrase and the cofactor LEDGF/p75
  作者：Giuliana Cuzzucoli Crucitti、Luca Pescatori、Antonella Messore、Valentina Noemi Madia、Giovanni Pupo、Francesco Saccoliti、Luigi Scipione、Silvano Tortorella、Francesco Saverio Di Leva、Sandro Cosconati、Ettore Novellino、Zeger Debyser、Frauke Christ、Roberta Costi、Roberto Di Santo

  DOI：10.1016/j.ejmech.2015.06.036

  日期：2015.8

  A series of N-aryl-naphthylamines, exemplified by the structures 11-16, were chosen for an in-house library screening to assay their ability to disrupt the interaction between the LEDGF cofactor and the HIV integrase. Structure modification led also to design and synthesize new compounds 17a-f. Compounds 11e,h,k,n, 13b, and 14 showed good activity in AlphaScreen assay. The most active compound lie (IC50 = 2.5 mu M) was selected for molecular modeling studies and showed a binding mode similar to the one of the known LEDGIN 8. (C) 2015 Elsevier Masson SAS. All rights reserved.