3-carboxy-2,2,5,5-tetramethyl-1-pyrrolidinyloxy free radical | 13810-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-carboxy-2,2,5,5-tetramethyl-1-pyrrolidinyloxy free radical
• 英文别名: 2,2,5,5-tetramethyl-1-oxylopyrrolin-3-carboxanhydride；Anhydrid v.3-Carboxy-2,2,5,5-tetramethyl-pyrrolin-1-oxyl
• CAS: 13810-30-5
• 化学式: C₁₈H₂₆N₂O₅
• 分子量: 350.415
• InChiKey: JIAKOZQFBXNTDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89.65
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-carboxy-2,2,5,5-tetramethyl-1-pyrrolidinyloxy free radical 在 盐酸 、 三氯化铝 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Hideg, Kalman; Cseko, Jozsef; Hankovszky, H. Olga, Synthetic Communications, 1986, vol. 16, # 14, p. 1839 - 1848

  摘要：

  DOI：
• 作为产物：
  描述：

  3-carboxy-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-carboxy-2,2,5,5-tetramethyl-1-pyrrolidinyloxy free radical
  参考文献：
  名称：

  [EN] NITROXIDE CONTAINING AMYLOID BINDING AGENTS FOR IMAGING AND THERAPEUTIC USES
  [FR] AGENTS DE LIAISON À L'AMYLOÏDE CONTENANT DU NITROXYDE UTILISÉS EN IMAGERIE ET À DES FINS THÉRAPEUTIQUES

  摘要：

  本发明提供了使用亚硝基自旋标记的淀粉样β结合化合物来成像淀粉样物质的方法。本发明还提供了亚硝基自旋标记的淀粉样β结合化合物。

  公开号：

  WO2017031239A1

文献信息

• Synthesis and structure of products of hydroxylamine acylation with 3-carboxy-2,2,5,5-tetramethylpyrrolinoxyl derivatives
  作者：V. D. Sen’、G. V. Shilov、V. A. Golubev

  DOI：10.1134/s1070428009080132

  日期：2009.8

  The reaction of NH2OH with the derivatives of 2,2,5,5-tetramethylpyrrolin-1-oxyl-3-carboxylic acid in all events led to the formation of a mixture of the corresponding nitroxylhydroxamic acid with a stable O-acylhydroxylamine. The ratio between the products depends on the nature of the acylating agent and under the Studied conditions varies from similar to 5.5 : 1 to 1 : 3 indicating the comparable nucleophilicity in this reaction of N and O atoms in the hydroxylamine. The most active chloride of the mentioned acid alongside the indicated products afforded in a considerable yield N,O-diacylhydroxylamine and the triacylated hydroxylamine, 3-[(2,2,5,5-tetramethyl-1-oxylopyrrolin-3-yl)carbonyloxyimino][(2,2,5,5-tetramethyl-1-oxylopyrrolin-3-yl)carbonyloxy]methyl}-2,2,5,5-tetramethylpyrrolin-1-oxyl. The structure of both latter compounds was established by XRD analysis.
• Binding of Fluorescent and Spin-Labeled C-Terminal Hirudin Analogs to Thrombin
  作者：Sornampillai Sankarapandi、Judith K. Woodford、John L. Krstenansky、Lawrence J. Berliner

  DOI：10.1021/jm00048a022

  日期：1994.10

  Synthetic peptides based on the sequence of the negatively charged carboxyl tail of hirudin exhibit anticoagulant activity. Several antithrombin agents are being developed by chemical and structural optimization of these ''hirupeptides''. The present work demonstrates the design and use of novel spin-labeled and fluorescent-labeled C-terminal hirudin analogs to study the interactions of these antithrombin agents with thrombin in solution. Three labeled hirulabels were synthesized based upon the amino acid sequence of the antithrombin agent MDL 28050, X-NH-(CH2)(7)-CO-Asp-Tyr-Glu-Pro-Ile-Pro-G where X = anthraniloyl, 1,5-dansyl, or 3-carbamoyl-2,2,5,5-tetramethyl-3-pyrrol The modifications did not significantly alter the potency of these inhibitors which showed Ki values of 100 nM. Their interactions with human and bovine thrombin were studied by ESR and fluorescence techniques. The spin-labeled hirupeptide was able to discern subtle differences in binding to human versus: bovine thrombin. The 8-aminooctanoic acid spacer arm placed the nitroxide moieties near the active site, near regions of the autolysis loops which differentiates between human alpha- and gamma-thrombin. It was also able to discern paramagnetic quenching and fluorescence energy transfer interactions, respectively, between covalently attached spin labels and fluorescent probes at the active site Ser 195 and the fluorophore on the hirupeptide.