N-[1,2-dithiolane-3-pentanoyl]-L-glutamyl-L-alanine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[1,2-dithiolane-3-pentanoyl]-L-glutamyl-L-alanine
• 英文别名: N-(R/S)-lipoyl-L-glutamyl-L-alanine；Lip-LGlu-LAla-OH；R/SLip-LGlu-LAla-OH；R/SLip-EA-OH；(4S)-5-[[(1S)-1-carboxyethyl]amino]-4-[5-(dithiolan-3-yl)pentanoylamino]-5-oxopentanoic acid
• 化学式: C₁₆H₂₆N₂O₆S₂
• 分子量: 406.524
• InChiKey: MQXRTCVZPIHBLD-PRWSFJOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  183
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  谷丙二肽 、 DL-α-硫辛酸-NHS 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 生成 N-[1,2-dithiolane-3-pentanoyl]-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

文献信息

• Compositions And Methods For Treating Ischemia And Ischemia-Reperfusion Injury
  申请人：Ischemix LLC

  公开号：US20160264622A1

  公开（公告）日：2016-09-15

  The present invention relates to compositions comprising a substantially pure compound represented by Structural Formula I: and methods of using such compounds to activate cytoprotective kinases. The values and preferred values of the variables in Structural Formula I are defined herein.

  本发明涉及包含由结构式I代表的基本纯化合物的组合物，以及利用这些化合物来激活细胞保护激酶的方法。结构式I中变量的值和首选值在本文中有定义。
• [EN] COMPOSITIONS AND METHODS FOR TREATING ISCHEMIA AND ISCHEMIA-REPERFUSION INJURY<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DE L'ISCHÉMIE ET DE LA LÉSION DE L'ISCHÉMIE-REPERFUSION
  申请人：ISCHEMIX LLC

  公开号：WO2010132657A1

  公开（公告）日：2010-11-18

  The present invention relates, in some embodiments, to compositions comprising a substantially pure compound represented by Structural Formula (I) and methods of using such compounds to activate cytoprotective kinases. In additional embodiments, the invention relates to methods for treating an ischemia or an ischemia-reperfusion injury in a subject, comprising administering to the subject an effective amount of a compound of the invention (e.g., in multiple doses). The values and preferred values of the variables in Structural Formula (I) are defined herein.

  本发明涉及一些实施例中包含由结构式（I）表示的基本纯化化合物的组合物及其使用方法，以激活细胞保护激酶。在其他实施例中，本发明涉及治疗缺血或缺血再灌注损伤的方法，包括向受试者施用本发明化合物的有效量（例如，多次剂量）。结构式（I）中变量的值和优选值在此定义。
• COMPOSITIONS AND METHODS FOR TREATING ISCHEMIA AND ISCHEMIA-REPERFUSION INJURY
  申请人：Baguisi Alexander

  公开号：US20110160294A1

  公开（公告）日：2011-06-30

  The present invention relates to compositions comprising a substantially pure compound represented by Structural Formula I: and methods of using such compounds to activate cytoprotective kinases. The values and preferred values of the variables in Structural Formula I are defined herein.

  本发明涉及包含由结构式I表示的基本纯化化合物的组合物以及使用这种化合物激活细胞保护激酶的方法。结构式I中变量的值和优选值在此定义。
• US20140274917A1
  申请人：——

  公开号：US20140274917A1

  公开（公告）日：2014-09-18
• US7928067B2
  申请人：——

  公开号：US7928067B2

  公开（公告）日：2011-04-19