2-oxyl-1,1,3,3-tetramethyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-6-carbaldehyde | 1196848-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 2-oxyl-1,1,3,3-tetramethyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-6-carbaldehyde
• CAS: 1196848-46-0
• 化学式: C₁₂H₁₅N₂O₂
• 分子量: 219.263
• InChiKey: LIDVIJQYKROXFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxyl-1,1,3,3-tetramethyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-6-carbaldehyde 在 dimethyl(1-diazo-2-oxopropyl)phosphonate 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以37%的产率得到6-ethynyl-1,1,3,3-tetramethyl-1H-pyrrolo[3,4-c]pyridin-2-yloxyl radical
  参考文献：
  名称：

  具有乙炔基官能团的新型硝基吡咯啉的合成

  摘要：

  摘要 通过顺磁性醛与（1-重氮-2-氧代丙基）膦酸二甲酯（Bestmann-Ohira 试剂）的反应，获得了含有一个或两个乙炔基的 3-取代和 3,4-二取代吡咯啉氮氧化物。发现含有乙炔基的新化合物在 Sonogashira 偶联、环化和环加成反应中是有用的构件，产生潜在的“叠氮基特异性”交联自旋标记、顺磁性配体和多自由基支架。图形概要

  DOI：

  10.1080/00397911.2015.1066391
• 作为产物：
  描述：

  1,3-Diydro-6-hydroxymethyl-1,1,3,3-tetramethyl-2H-pyrrolo[3,4-c]pyridin-2-yloxyl radical 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以44%的产率得到2-oxyl-1,1,3,3-tetramethyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-6-carbaldehyde
  参考文献：
  名称：

  New Poly(ADP-ribose) Polymerase-1 Inhibitors with Antioxidant Activity Based on 4-Carboxamidobenzimidazole-2-ylpyrroline and -tetrahydropyridine Nitroxides and Their Precursors

  摘要：

  4-Carboxamidobenzimidazoles were previously described as PARP inhibitor compounds. Here we report upon 4-carboxamido-1H-benzimidazoles substituted in the 2-position with nitroxides or their amine or hydroxylamine precursors. Among the new molecules, a highly active PARP inhibitor 4h (IC50 = 14 nM) was identified with antioxidant/radical scavenger activity. We concluded that in most cases sterically hindered amines are better PARP inhibitors than their oxidized form and structural changes in the 2-substituted 4-carboxamido-1H-benzimidazoles (such as N-substitution or changing the position of the carboxamide group) were detrimental to PARP inhibition activity but not to antioxidant activity. These results indicate the advantages of combining an antioxidant nitroxide or nitroxide precursor with a PARP inhibitor molecule to decrease or eliminate the deleterious processes initiated by reactive oxygen and reactive nitrogen species (ROS and RNS). The radical scavenging capability of 4h was demonstrated by EPR study of urine collected after drug administration.

  DOI：

  10.1021/jm801476y

文献信息

• New Poly(ADP-ribose) Polymerase-1 Inhibitors with Antioxidant Activity Based on 4-Carboxamidobenzimidazole-2-ylpyrroline and -tetrahydropyridine Nitroxides and Their Precursors
  作者：Tamás Kálai、Mária Balog、Alíz Szabó、Gergely Gulyás、József Jekő、Balázs Sümegi、Kálmán Hideg

  DOI：10.1021/jm801476y

  日期：2009.3.26

  4-Carboxamidobenzimidazoles were previously described as PARP inhibitor compounds. Here we report upon 4-carboxamido-1H-benzimidazoles substituted in the 2-position with nitroxides or their amine or hydroxylamine precursors. Among the new molecules, a highly active PARP inhibitor 4h (IC50 = 14 nM) was identified with antioxidant/radical scavenger activity. We concluded that in most cases sterically hindered amines are better PARP inhibitors than their oxidized form and structural changes in the 2-substituted 4-carboxamido-1H-benzimidazoles (such as N-substitution or changing the position of the carboxamide group) were detrimental to PARP inhibition activity but not to antioxidant activity. These results indicate the advantages of combining an antioxidant nitroxide or nitroxide precursor with a PARP inhibitor molecule to decrease or eliminate the deleterious processes initiated by reactive oxygen and reactive nitrogen species (ROS and RNS). The radical scavenging capability of 4h was demonstrated by EPR study of urine collected after drug administration.
• Synthesis of New Pyrroline Nitroxides with Ethynyl Functional Group
  作者：Györgyi Úr、Tamás Kálai、Mária Balog、Balázs Bognár、Gergely Gulyás-Fekete、Kálmán Hideg

  DOI：10.1080/00397911.2015.1066391

  日期：2015.9.17

  Abstract 3-Substituted and 3,4-disubstituted pyrroline nitroxides containing an ethynyl group or two ethynyl groups were achieved by the reaction of a paramagnetic aldehydes with dimethyl (1-diazo-2-oxopropyl)phosphonate (Bestmann–Ohira reagent). The new compounds containing an ethynyl group were found to be useful building blocks in Sonogashira coupling, cyclization, and cycloaddition reactions producing

  摘要 通过顺磁性醛与（1-重氮-2-氧代丙基）膦酸二甲酯（Bestmann-Ohira 试剂）的反应，获得了含有一个或两个乙炔基的 3-取代和 3,4-二取代吡咯啉氮氧化物。发现含有乙炔基的新化合物在 Sonogashira 偶联、环化和环加成反应中是有用的构件，产生潜在的“叠氮基特异性”交联自旋标记、顺磁性配体和多自由基支架。图形概要