N-benzyl-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide | 1383785-54-3

• 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-benzyl-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide
• 英文别名: N-benzyl-2-hydroxy-1,3-dioxo-1,2,3,4-tetrahydroisoiuinoline-4-carboxamide；N-benzyl-2-hydroxy-1,3-dioxo-4H-isoquinoline-4-carboxamide
• CAS: 1383785-54-3
• 化学式: C₁₇H₁₄N₂O₄
• 分子量: 310.309
• InChiKey: KLDKRHZXVJYNGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 2-(benzyloxy)-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate 在 三氯化硼 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.25h， 生成 N-benzyl-2-hydroxy-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

• [EN] 2-HYDROXYISOQUINOLINE-1,3(2H,4H)-DIONES AND RELATED COMPOUNDS USEFUL AS HIV REPLICATION INHIBITORS<br/>[FR] 2 -HYDROXYISOQUINOLINE- 1, 3 ( 2H, 4H) - DIONES ET COMPOSÉS ASSOCIÉS SERVANT D'INHIBITEURS DE LA RÉPLICATION DU VIH
  申请人：UNIV LEUVEN KATH

  公开号：WO2012085003A1

  公开（公告）日：2012-06-28

  The present invention relates to compounds and compositions acting as inhibitors of HIV integrase. The compound of the invention is of Formula (I), or a tautomer (I') thereof, or a pharmaceutically acceptable salt, or solvate of said compound or tautomer thereof, wherein R1, R2, R3, R4, R5 and R6 have defined meanings.

  本发明涉及作为HIV整合酶抑制剂的化合物和组合物。该发明的化合物为式(I)的化合物，或其互变异构体(I')，或所述化合物或其互变异构体的药用可接受盐或溶剂，其中R1、R2、R3、R4、R5和R6具有定义的含义。
• N-HYDROXYISOQUINOLINEDIONE INHIBITORS OF HBV REPLICATION
  申请人：Saint Louis University

  公开号：US20190070165A1

  公开（公告）日：2019-03-07

  In some aspects, the present disclosure provides compounds of the formula: Formula (I) wherein the variables are defined herein are provided, which may be used to inhibit viral replication. In some embodiments, these compounds may be used to treat an infection of hepatitis B virus.
• [EN] N-HYDROXYISOQUINOLINEDIONE INHIBITORS OF HBV REPLICATION<br/>[FR] INHIBITEURS DE RÉPLICATION DU VHB DE TYPE N-HYDROXYISOQUINOLINEDIONE
  申请人：UNIV SAINT LOUIS

  公开号：WO2017161133A1

  公开（公告）日：2017-09-21

  In some aspects, the present disclosure provides compounds of the formula: Formula (I) wherein the variables are defined herein are provided, which may be used to inhibit viral replication. In some embodiments, these compounds may be used to treat an infection of hepatitis B virus.
• 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.