N-(1,2-dithiolane-3-pentanoyl)-1,2-phenylenediamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: N-(1,2-dithiolane-3-pentanoyl)-1,2-phenylenediamine
• 英文别名: N-(2-aminophenyl)-5-(1,2-dithiolan-3-yl)-pentanamide；N-(2-aminophenyl)-5-(dithiolan-3-yl)pentanamide
• 化学式: C₁₄H₂₀N₂OS₂
• 分子量: 296.458
• InChiKey: UODYGDTZFLPBCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻苯二胺 、 Thioctic acid 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到N-(1,2-dithiolane-3-pentanoyl)-1,2-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.