N-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-1,3-phenylenediamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-1,3-phenylenediamine
• 英文别名: N-(3-aminophenyl)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide
• 化学式: C₂₀H₂₄N₂O₃
• 分子量: 340.422
• InChiKey: ZYVYLEHVKLPWEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,S)-硫辛酰氯 、 N-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-1,3-phenylenediamine 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以28%的产率得到N-[3-[5-(dithiolan-3-yl)pentanoylamino]phenyl]-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide
  参考文献：
  名称：

  Novel Potent Inhibitors of Lipid Peroxidation with Protective Effects against Reperfusion Arrhythmias

  摘要：

  A series of new compounds that contain lipoic acid and trolox connected through spacers were synthesized and examined for their antioxidant activity and their protective effects against reperfusion arrhythmias in isolated heart preparations. All compounds tested are strong inhibitors of lipid peroxidation. in rat liver microsomal membranes induced by ferrous ions and ascorbate. N-(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-N'-(1,2-dithiolane-3-pentanoyl)-1,2-phenylenediamine (13) exhibits anti-lipid peroxidation activity at the nanomolar range. N-(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-N'-(1,2-dithiolane-3-pentanoyl)ethylenediamine (10) and 13 totally suppressed reperfusion arrhythmias.

  DOI：

  10.1021/jm010962w
• 作为产物：
  描述：

  间苯二胺 、 奎诺二甲基丙烯酸酯 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以59%的产率得到N-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-1,3-phenylenediamine
  参考文献：
  名称：

  Novel Potent Inhibitors of Lipid Peroxidation with Protective Effects against Reperfusion Arrhythmias

  摘要：

  A series of new compounds that contain lipoic acid and trolox connected through spacers were synthesized and examined for their antioxidant activity and their protective effects against reperfusion arrhythmias in isolated heart preparations. All compounds tested are strong inhibitors of lipid peroxidation. in rat liver microsomal membranes induced by ferrous ions and ascorbate. N-(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-N'-(1,2-dithiolane-3-pentanoyl)-1,2-phenylenediamine (13) exhibits anti-lipid peroxidation activity at the nanomolar range. N-(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-N'-(1,2-dithiolane-3-pentanoyl)ethylenediamine (10) and 13 totally suppressed reperfusion arrhythmias.

  DOI：

  10.1021/jm010962w

文献信息

• Novel Potent Inhibitors of Lipid Peroxidation with Protective Effects against Reperfusion Arrhythmias
  作者：Maria Koufaki、Theodora Calogeropoulou、Anastasia Detsi、Aristidis Roditis、Angeliki P. Kourounakis、Panagiota Papazafiri、Karyofyllis Tsiakitzis、Catherine Gaitanaki、Isidoros Beis、Panos N. Kourounakis

  DOI：10.1021/jm010962w

  日期：2001.11.1

  A series of new compounds that contain lipoic acid and trolox connected through spacers were synthesized and examined for their antioxidant activity and their protective effects against reperfusion arrhythmias in isolated heart preparations. All compounds tested are strong inhibitors of lipid peroxidation. in rat liver microsomal membranes induced by ferrous ions and ascorbate. N-(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-N'-(1,2-dithiolane-3-pentanoyl)-1,2-phenylenediamine (13) exhibits anti-lipid peroxidation activity at the nanomolar range. N-(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-N'-(1,2-dithiolane-3-pentanoyl)ethylenediamine (10) and 13 totally suppressed reperfusion arrhythmias.