1-acetyl-3-formyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-acetyl-3-formyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole
• 英文别名: 1-Acetyl-2,2,5,5-tetramethylpyrrole-3-carbaldehyde
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: AJCXZDINMYBBJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-二甲基吡咯 、 1-acetyl-3-formyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole 在 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 11.17h， 以30%的产率得到
  参考文献：
  名称：

  Synthesis of paramagnetic BODIPY dyes as new double (spin and fluorescence) sensors

  摘要：

  Paramagnetic pyrroline and 1,2,3,6-tetrahydropyridine derivatives of BODIPY and their diamagnetic analogs have been synthesized and characterized as novel redox double sensor and cation sensitive reagents. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.107
• 作为产物：
  描述：

  乙酰氯 、 2,2,5,5-四甲基-2,5-二氢-1H-吡咯-3-甲醛 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到1-acetyl-3-formyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole
  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 paramagnetic BODIPY dyes as new double (spin and fluorescence) sensors
  作者：Tamás Kálai、Éva Hideg、József Jekő、Kálmán Hideg

  DOI：10.1016/j.tetlet.2003.09.107

  日期：2003.11

  Paramagnetic pyrroline and 1,2,3,6-tetrahydropyridine derivatives of BODIPY and their diamagnetic analogs have been synthesized and characterized as novel redox double sensor and cation sensitive reagents. (C) 2003 Elsevier Ltd. All rights reserved.