5-[1,2]Dithiolan-3-yl-pentanoic acid [2-(5-methoxy-1H-indol-3-yl)-ethyl]-amide | 214555-17-6

• 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-pentanoic acid [2-(5-methoxy-1H-indol-3-yl)-ethyl]-amide
• 英文别名: 5-(1,2-dithiolan-3-yl)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)pentanamide；5-(dithiolan-3-yl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]pentanamide
• CAS: 214555-17-6
• 化学式: C₁₉H₂₆N₂O₂S₂
• 分子量: 378.56
• InChiKey: HYDGZQMQXIFYIO-UHFFFAOYSA-N

物化性质

• 沸点：
  642.7±45.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[1,2]Dithiolan-3-yl-pentanoic acid [2-(5-methoxy-1H-indol-3-yl)-ethyl]-amide 在 potassium bromide 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, pulse radiolysis, and in vitro radioprotection studies of melatoninolipoamide, a novel conjugate of melatonin and α-lipoic acid

  摘要：

  A novel conjugate of melatonin 2 and alpha-lipoic acid 4 has been prepared using DCC mediated coupling. The conjugate named melatoninolipoamide has been assigned its structure 1 on the basis of spectral analysis (UV, IR, NMR, and EI-MS). Pulse radiolysis studies of the conjugate were carried out in aqueous solutions with both oxidizing and reducing radicals. The results indicate that the melatonin moiety of the conjugate reacts preferably with oxidizing radicals and the lipoic acid moiety exhibits preferential reaction with reducing radicals. The in vitro radioprotection ability of 1 was examined by gamma-radiation induced lipid peroxidation in liposomes and hemolysis of erythrocytes, and compared the results with those of melatonin and alpha-lipoic acid. The studies suggest that the conjugate can be explored as a probable radioprotector. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.042
• 作为产物：
  描述：

  褪黑素 在 硫酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 5-[1,2]Dithiolan-3-yl-pentanoic acid [2-(5-methoxy-1H-indol-3-yl)-ethyl]-amide
  参考文献：
  名称：

  Synthesis, pulse radiolysis, and in vitro radioprotection studies of melatoninolipoamide, a novel conjugate of melatonin and α-lipoic acid

  摘要：

  A novel conjugate of melatonin 2 and alpha-lipoic acid 4 has been prepared using DCC mediated coupling. The conjugate named melatoninolipoamide has been assigned its structure 1 on the basis of spectral analysis (UV, IR, NMR, and EI-MS). Pulse radiolysis studies of the conjugate were carried out in aqueous solutions with both oxidizing and reducing radicals. The results indicate that the melatonin moiety of the conjugate reacts preferably with oxidizing radicals and the lipoic acid moiety exhibits preferential reaction with reducing radicals. The in vitro radioprotection ability of 1 was examined by gamma-radiation induced lipid peroxidation in liposomes and hemolysis of erythrocytes, and compared the results with those of melatonin and alpha-lipoic acid. The studies suggest that the conjugate can be explored as a probable radioprotector. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.042

文献信息

• Syntheses of Novel Indole Lipoic Acid Derivatives and Their Antioxidant Effects on Lipid Peroxidation
  作者：A. Selen Gurkan、Arzu Karabay、Zeliha Buyukbingol、Adeboye Adejare、Erdem Buyukbingol

  DOI：10.1002/ardp.200400932

  日期：2005.3

  properties of conjugates based on indole and lipoic acid moieties. The design and syntheses of novel indole α‐lipoic acid derivatives were performed. The antioxidant properties of target compounds were investigated using rat liver microsomal, NADPH‐dependent lipid peroxidation inhibition. Some of the target compounds, especially those containing amide linker at position 5 of indole ring, proved to be highly

  该研究的目的是检查基于吲哚和硫辛酸部分的缀合物的抗氧化特性。进行了新型吲哚α-硫辛酸衍生物的设计和合成。使用大鼠肝微粒体、NADPH 依赖性脂质过氧化抑制研究了目标化合物的抗氧化特性。与α-硫辛酸相比，一些目标化合物，特别是那些在吲哚环的第5位含有酰胺接头的化合物，被证明在抑制脂质过氧化方面非常有效。
• Synthesis, pulse radiolysis, and in vitro radioprotection studies of melatoninolipoamide, a novel conjugate of melatonin and α-lipoic acid
  作者：S VENKATACHALAM、A SALASKAR、A CHATTOPADHYAY、A BARIK、B MISHRA、R GANGABHAGIRATHI、K PRIYADARSINI

  DOI：10.1016/j.bmc.2006.05.042

  日期：2006.9.15

  A novel conjugate of melatonin 2 and alpha-lipoic acid 4 has been prepared using DCC mediated coupling. The conjugate named melatoninolipoamide has been assigned its structure 1 on the basis of spectral analysis (UV, IR, NMR, and EI-MS). Pulse radiolysis studies of the conjugate were carried out in aqueous solutions with both oxidizing and reducing radicals. The results indicate that the melatonin moiety of the conjugate reacts preferably with oxidizing radicals and the lipoic acid moiety exhibits preferential reaction with reducing radicals. The in vitro radioprotection ability of 1 was examined by gamma-radiation induced lipid peroxidation in liposomes and hemolysis of erythrocytes, and compared the results with those of melatonin and alpha-lipoic acid. The studies suggest that the conjugate can be explored as a probable radioprotector. (c) 2006 Elsevier Ltd. All rights reserved.