DL=α-lipothioamide

• 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: DL=α-lipothioamide
• 英文别名: 5-(Dithiolan-3-yl)pentanethioamide；5-(dithiolan-3-yl)pentanethioamide
• 化学式: C₈H₁₅NS₃
• 分子量: 221.412
• InChiKey: UDMOSCWQCFUMSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  DL=α-lipothioamide 、 溴代-3,4-二甲氧基苯乙酮 以 乙醇 为溶剂， 反应 2.0h， 以29%的产率得到2-(4-(1,2-Dithiolan-3-yl)butyl)-4-(3,4-dimethoxyphenyl)thiazole
  参考文献：
  名称：

  Design and synthesis of 1,2-dithiolane derivatives and evaluation of their neuroprotective activity

  摘要：

  We designed and synthesized new analogues containing 1,2-dithiolane-3-alkyl and protected or free catechol moieties connected through heteroaromatic rings such as triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, tetrazole or thiazole in order to explore the influence of the bioisosteric replacement of the amide group on the neuroprotective activity of the lipoic acid/dopamine conjugate. Evaluation of the activity of the new compounds, using glutamate-challenged hippocampal HT22 cells, showed that incorporation of heteroaromatic rings in the alkyl-1,2-dithiolane moieties in conjunction with another antioxidant, in this case catechol, may result in strong neuroprotective activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.036
• 作为产物：
  描述：

  (+/-)-alpha-硫辛酰胺 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到DL=α-lipothioamide
  参考文献：
  名称：

  Design and synthesis of 1,2-dithiolane derivatives and evaluation of their neuroprotective activity

  摘要：

  We designed and synthesized new analogues containing 1,2-dithiolane-3-alkyl and protected or free catechol moieties connected through heteroaromatic rings such as triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, tetrazole or thiazole in order to explore the influence of the bioisosteric replacement of the amide group on the neuroprotective activity of the lipoic acid/dopamine conjugate. Evaluation of the activity of the new compounds, using glutamate-challenged hippocampal HT22 cells, showed that incorporation of heteroaromatic rings in the alkyl-1,2-dithiolane moieties in conjunction with another antioxidant, in this case catechol, may result in strong neuroprotective activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.036

文献信息

• Design and synthesis of 1,2-dithiolane derivatives and evaluation of their neuroprotective activity
  作者：Maria Koufaki、Christina Kiziridi、Faidra Nikoloudaki、Michael N. Alexis

  DOI：10.1016/j.bmcl.2007.05.036

  日期：2007.8

  We designed and synthesized new analogues containing 1,2-dithiolane-3-alkyl and protected or free catechol moieties connected through heteroaromatic rings such as triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, tetrazole or thiazole in order to explore the influence of the bioisosteric replacement of the amide group on the neuroprotective activity of the lipoic acid/dopamine conjugate. Evaluation of the activity of the new compounds, using glutamate-challenged hippocampal HT22 cells, showed that incorporation of heteroaromatic rings in the alkyl-1,2-dithiolane moieties in conjunction with another antioxidant, in this case catechol, may result in strong neuroprotective activity. (c) 2007 Elsevier Ltd. All rights reserved.