5-(1,2-dithiolan-3-yl)-1-(4-methylpiperazin-1-yl)pentan-1-one hydrochloride

• 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: 5-(1,2-dithiolan-3-yl)-1-(4-methylpiperazin-1-yl)pentan-1-one hydrochloride
• 英文别名: 5-(Dithiolan-3-yl)-1-(4-methylpiperazin-1-yl)pentan-1-one;hydrochloride；5-(dithiolan-3-yl)-1-(4-methylpiperazin-1-yl)pentan-1-one;hydrochloride
• 化学式: C₁₃H₂₄N₂OS₂*ClH
• 分子量: 324.939
• InChiKey: JVZIANXXVPGFPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 Thioctic acid 在 N,N'-二环己基碳二亚胺 、 盐酸 作用下， 以 二氯甲烷 、 乙醚 、 水 为溶剂， 反应 3.17h， 以20%的产率得到5-(1,2-dithiolan-3-yl)-1-(4-methylpiperazin-1-yl)pentan-1-one hydrochloride
  参考文献：
  名称：

  Design and Synthesis of New Bifunctional Sigma-1 Selective Ligands with Antioxidant Activity

  摘要：

  Herein we report the synthesis of new bifunctional sigma-1 (sigma(1))-selective ligands with antioxidant activity. To achieve this goal, we combined the structure of lipoic acid, a universal antioxidant, with an appropriate sigma aminic moiety. Ligands 14 and 26 displayed high affinity and selectivity for sigma(1) receptors (K-i sigma(1) = 1.8 and 5.5 nM; K-i sigma(2)/sigma(1) = 354 and 414, respectively). Compound 26 exhibited in vivo antiopioid effects on kappa opioid (KOP) receptor-mediated analgesia. In rat liver and brain mitochondria (RLM, RBM), this compound significantly reduced the swelling and the oxidation of thiol groups induced by calcium ions. Our results demonstrate that the tested compound has protective effects against oxidative stress.

  DOI：

  10.1021/jm3017893

文献信息

• Design and Synthesis of New Bifunctional Sigma-1 Selective Ligands with Antioxidant Activity
  作者：O. Prezzavento、E. Arena、C. Parenti、L. Pasquinucci、G. Aricò、G. M. Scoto、S. Grancara、A. Toninello、S. Ronsisvalle

  DOI：10.1021/jm3017893

  日期：2013.3.28

  Herein we report the synthesis of new bifunctional sigma-1 (sigma(1))-selective ligands with antioxidant activity. To achieve this goal, we combined the structure of lipoic acid, a universal antioxidant, with an appropriate sigma aminic moiety. Ligands 14 and 26 displayed high affinity and selectivity for sigma(1) receptors (K-i sigma(1) = 1.8 and 5.5 nM; K-i sigma(2)/sigma(1) = 354 and 414, respectively). Compound 26 exhibited in vivo antiopioid effects on kappa opioid (KOP) receptor-mediated analgesia. In rat liver and brain mitochondria (RLM, RBM), this compound significantly reduced the swelling and the oxidation of thiol groups induced by calcium ions. Our results demonstrate that the tested compound has protective effects against oxidative stress.