N-(4-fluorobenzyl)-2-methyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide | 1436490-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-(4-fluorobenzyl)-2-methyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide
• 英文别名: N-[(4-fluorophenyl)methyl]-2-methyl-1,3-dioxo-4H-isoquinoline-4-carboxamide
• CAS: 1436490-25-3
• 化学式: C₁₈H₁₅FN₂O₃
• 分子量: 326.327
• InChiKey: LMAJIEZDWRZDCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-methoxy-2-[2-(methoxycarbonyl)phenyl]-3-oxopropanoic acid 在 氯化亚砜 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 16.0h， 生成 N-(4-fluorobenzyl)-2-methyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide
  参考文献：
  名称：

  4-Substituted 2-Hydroxyisoquinoline-1,3(2H,4H)-diones as a Novel Class of HIV-1 Integrase Inhibitors

  摘要：

  A series of 2-hydroxy-1,3-dioxoisoquinoline-4-carboxamides featuring an N-hydroxyimide chelating functionality was evaluated for their inhibitory properties against human immunodeficiency virus type 1 integrase (HIV-1 IN). Several derivatives displayed low nanomolar IC50 values comparable to that of the clinically used raltegravir. A marked effect of one compound on both primary IN-catalyzed reactions, strand transfer (ST), and 3' processing (3'-P), emphasizes a novel IN inhibition mechanism establishing it as a potential new generation IN inhibitor. Substitution of the 2-hydroxyisoquinoline-1,3-dione scaffold at position 4 by carboxamido, chains was beneficial for antiviral activity since reproducible low micromolar anti-HIV activities were obtained for the first time within this scaffold.

  DOI：

  10.1021/ml400009t

文献信息

• 4-Substituted 2-Hydroxyisoquinoline-1,3(2<i>H</i>,4<i>H</i>)-diones as a Novel Class of HIV-1 Integrase Inhibitors
  作者：Muriel Billamboz、Virginie Suchaud、Fabrice Bailly、Cedric Lion、Jonas Demeulemeester、Christina Calmels、Marie-Line Andréola、Frauke Christ、Zeger Debyser、Philippe Cotelle

  DOI：10.1021/ml400009t

  日期：2013.7.11

  A series of 2-hydroxy-1,3-dioxoisoquinoline-4-carboxamides featuring an N-hydroxyimide chelating functionality was evaluated for their inhibitory properties against human immunodeficiency virus type 1 integrase (HIV-1 IN). Several derivatives displayed low nanomolar IC50 values comparable to that of the clinically used raltegravir. A marked effect of one compound on both primary IN-catalyzed reactions, strand transfer (ST), and 3' processing (3'-P), emphasizes a novel IN inhibition mechanism establishing it as a potential new generation IN inhibitor. Substitution of the 2-hydroxyisoquinoline-1,3-dione scaffold at position 4 by carboxamido, chains was beneficial for antiviral activity since reproducible low micromolar anti-HIV activities were obtained for the first time within this scaffold.