(2,5-Dioxopyrrolidin-1-yl) 5-[(3S)-dithiolan-3-yl]pentanoate

• 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: (2,5-Dioxopyrrolidin-1-yl) 5-[(3S)-dithiolan-3-yl]pentanoate
• 化学式: C₁₂H₁₇NO₄S₂
• 分子量: 303.403
• InChiKey: WBCUIGFYTHUQHZ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  谷丙二肽 、 (2,5-Dioxopyrrolidin-1-yl) 5-[(3S)-dithiolan-3-yl]pentanoate 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 生成 N-(S)-lipoyl-L-glutamyl-L-alanine
  参考文献：
  名称：

  Lipoic acid analogs with enhanced pharmacological activity

  摘要：

  Lipoic acid (1,2-dithiolane-3-pentanoic acid) is a pharmacophore with unique antioxidant and cytoprotective properties. We synthesized a library based upon the condensation of natural and unnatural amino acids with the carboxylic acid moiety of lipoic acid. SAR studies were conducted using a cardiac ischemia-reperfusion animal model. Cytoprotective efficacy was associated with the R-enantiomer of the dithiolane. Potency of library compounds was dictated by the acidic strength of the adduct. alpha-N-[(R)1,2-dithiolane-3-pentanoyl]-L-glutamyl-L-alanine, designated CMX-2043, was chosen for further pharmacologic evaluation. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.057
• 作为产物：
  描述：

  N,N'-二琥珀酰亚胺基碳酸酯 、 左旋硫辛酸 在 N,N-二异丙基乙胺 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 (2,5-Dioxopyrrolidin-1-yl) 5-[(3S)-dithiolan-3-yl]pentanoate
  参考文献：
  名称：

  Lipoic acid analogs with enhanced pharmacological activity

  摘要：

  Lipoic acid (1,2-dithiolane-3-pentanoic acid) is a pharmacophore with unique antioxidant and cytoprotective properties. We synthesized a library based upon the condensation of natural and unnatural amino acids with the carboxylic acid moiety of lipoic acid. SAR studies were conducted using a cardiac ischemia-reperfusion animal model. Cytoprotective efficacy was associated with the R-enantiomer of the dithiolane. Potency of library compounds was dictated by the acidic strength of the adduct. alpha-N-[(R)1,2-dithiolane-3-pentanoyl]-L-glutamyl-L-alanine, designated CMX-2043, was chosen for further pharmacologic evaluation. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.057

文献信息

• Lipoic acid analogs with enhanced pharmacological activity
  作者：Steven A. Kates、Ralph A. Casale、Alexander Baguisi、Reinier Beeuwkes

  DOI：10.1016/j.bmc.2013.10.057

  日期：2014.1

  Lipoic acid (1,2-dithiolane-3-pentanoic acid) is a pharmacophore with unique antioxidant and cytoprotective properties. We synthesized a library based upon the condensation of natural and unnatural amino acids with the carboxylic acid moiety of lipoic acid. SAR studies were conducted using a cardiac ischemia-reperfusion animal model. Cytoprotective efficacy was associated with the R-enantiomer of the dithiolane. Potency of library compounds was dictated by the acidic strength of the adduct. alpha-N-[(R)1,2-dithiolane-3-pentanoyl]-L-glutamyl-L-alanine, designated CMX-2043, was chosen for further pharmacologic evaluation. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.