N-[2-(3,4-dimethoxyphenyl)ethyl]-2-benzyloxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide | 1383785-94-1

• 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-[2-(3,4-dimethoxyphenyl)ethyl]-2-benzyloxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide
• 英文别名: N-[2-(3,4-dimethoxyphenyl)ethyl]-2-benzyloxy-1,3-dioxo1,2,3,4-tetrahydroisociuinoline-4-carboxamide；N-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-2-phenylmethoxy-4H-isoquinoline-4-carboxamide
• CAS: 1383785-94-1
• 化学式: C₂₇H₂₆N₂O₆
• 分子量: 474.513
• InChiKey: DSASTSYYAGOITB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[2-(3,4-dimethoxyphenyl)ethyl]-2-benzyloxy-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide 在 三溴化硼 作用下， 以95%的产率得到N-[2-(3,4-dihydroxyphenyl)ethyl]-2-hydroxy-1,3-dioxoisoquinoline-4-carboxamide
  参考文献：
  名称：

  [EN] 2-HYDROXYISOQUINOLINE-1,3(2H,4H)-DIONES AND RELATED COMPOUNDS USEFUL AS HIV REPLICATION INHIBITORS
  [FR] 2 -HYDROXYISOQUINOLINE- 1, 3 ( 2H, 4H) - DIONES ET COMPOSÉS ASSOCIÉS SERVANT D'INHIBITEURS DE LA RÉPLICATION DU VIH

  摘要：

  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。

  公开号：

  WO2012085003A1
• 作为产物：
  描述：

  methyl 2-{1-[(benzyloxy)amino]-3-methoxy-1,3-dioxopropan-2-yl}benzoate 在 potassium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 12.5h， 生成 N-[2-(3,4-dimethoxyphenyl)ethyl]-2-benzyloxy-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