N2,N2-dimethyl-N-[2-(6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[3,2-f]isoquinolin-1-yl)ethyl]glycinamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N2,N2-dimethyl-N-[2-(6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[3,2-f]isoquinolin-1-yl)ethyl]glycinamide
• 英文别名: 2-(dimethylamino)-N-(2-(6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[3,2-f]isoquinolin-1-yl)ethyl)acetamide；2-(dimethylamino)-N-[2-(6-oxo-3,7,8,9-tetrahydropyrrolo[3,2-f]isoquinolin-1-yl)ethyl]acetamide
• 化学式: C₁₇H₂₂N₄O₂
• 分子量: 314.387
• InChiKey: UKVMYPIDUCETTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  77.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-aminoethyl)-3,7,8,9-tetrahydro-6H-pyrrolo[3,2-f]isoquinolin-6-one 、 N,N-二甲基甘氨酸 在 PL-Mukaiyama 、 PS-dimethylaminopyridine 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N2,N2-dimethyl-N-[2-(6-oxo-6,7,8,9-tetrahydro-3H-pyrrolo[3,2-f]isoquinolin-1-yl)ethyl]glycinamide
  参考文献：
  名称：

  Identification of aminoethyl pyrrolo dihydroisoquinolinones as novel poly(ADP-ribose) polymerase-1 inhibitors

  摘要：

  PARP inhibitors have been demonstrated to retard intracellular DNA repair and therefore sensitize tumor cells to cytotoxic agents or ionizing radiation. We report the identification of a novel class of PARP1 inhibitors, containing a pyrrolo moiety fused to a dihydroisoquinolinone, derived from virtual screening of the proprietary collection. SAR exploration around the nitrogen of the aminoethyl appendage chain of 1 led to compounds that displayed low nanomolar activity in a PARP1 enzymatic assay. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.031

文献信息

• Identification of aminoethyl pyrrolo dihydroisoquinolinones as novel poly(ADP-ribose) polymerase-1 inhibitors
  作者：Danila Branca、Mauro Cerretani、Philip Jones、Uwe Koch、Federica Orvieto、Maria Cecilia Palumbi、Michael Rowley、Carlo Toniatti、Ester Muraglia

  DOI：10.1016/j.bmcl.2009.06.031

  日期：2009.8

  PARP inhibitors have been demonstrated to retard intracellular DNA repair and therefore sensitize tumor cells to cytotoxic agents or ionizing radiation. We report the identification of a novel class of PARP1 inhibitors, containing a pyrrolo moiety fused to a dihydroisoquinolinone, derived from virtual screening of the proprietary collection. SAR exploration around the nitrogen of the aminoethyl appendage chain of 1 led to compounds that displayed low nanomolar activity in a PARP1 enzymatic assay. (C) 2009 Elsevier Ltd. All rights reserved.