4-(2-Aminoacetamido)-2,2,6,6-tetramethyl-1-piperidinyloxy | 54231-62-8

• 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: 4-(2-Aminoacetamido)-2,2,6,6-tetramethyl-1-piperidinyloxy
• CAS: 54231-62-8
• 化学式: C₁₁H₂₂N₃O₂
• 分子量: 228.315
• InChiKey: LRUPIFRVHGUWHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  59.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-Aminoacetamido)-2,2,6,6-tetramethyl-1-piperidinyloxy 、 tris(8-carboxy-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d']bis[1,3]dithiol-4-yl)methyl 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以6.4 mg的产率得到4-[(8-carboxy-2,2,6,6-tetramethyl-[1,3]dithiolo[4,5-f][1,3]benzodithiol-4-yl)-[4-[C-hydroxy-N-[2-hydroxy-2-(2,2,6,6-tetramethyl-1-oxidopiperidin-4-yl)iminoethyl]carbonimidoyl]-2,2,6,6-tetramethyl-[1,3]dithiolo[4,5-f][1,3]benzodithiol-1-ium-8-ylidene]methyl]-2,2,6,6-tetramethyl-[1,3]dithiolo[4,5-f][1,3]benzodithiole-8-carboxylic acid
  参考文献：
  名称：

  Structural Factors Controlling the Spin–Spin Exchange Coupling: EPR Spectroscopic Studies of Highly Asymmetric Trityl–Nitroxide Biradicals

  摘要：

  Highly asymmetric exchange-coupled biradicals, e.g., the trityl-nitroxides (TNs), possess particular magnetic properties that have opened new possibilities for their application in biophysical, physicochemical, and biological studies. In the present work, we investigated the effect of the linker length on the spin-spin coupling interaction (J) in TN biradicals using the newly synthesized biradicals CT02-GT, CT02-AT, CT02-VT, and CT02-PPT as well as the previously reported biradicals TNN14 and TN1. The results show that the magnitude of J can be easily tuned from similar to 4 G (conformer 1 in CT02-PPT) to >1200 G (in TNN14) by varying the linker separating the two radical moieties and changing the temperature. Computer simulations of EPR spectra were carried out to estimate J values of the TN biradicals directly. In addition to the spin-spin coupling interaction of TN biradicals, their g, hyperfine-splitting, and zero-field-splitting interactions were explored at low temperature (220 K). Our present study clearly shows that varying the spin-spin interaction as a function of linker distance and temperature provides an effective strategy for the development of new TN biradicals that can find wide applications in relevant fields.

  DOI：

  10.1021/ja311571v
• 作为产物：
  描述：

  4-氨基-TEMPO 在 吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 4-(2-Aminoacetamido)-2,2,6,6-tetramethyl-1-piperidinyloxy
  参考文献：
  名称：

  Syntheses and Transglutaminase-Catalyzed Incorporation of Novel Spin-Labeled Primary Amines into Proteins

  摘要：

  A series of spin-labeled primary amine derivatives, namely, 2,2,6,6-tetramethyl-piperidinyl-1-oxyl-4-amidoalkylamines with varying alkyl chain lengths, have been synthesized. The spin-labeled primary amine with a tetramethylene or a pentamethylene chain covalently modifies human plasma fibronectin with a stoichiometry of 0.97-to-1.0 (probe-to-subunit) in the presence of coagulation factor XIIIa. The labels with two or one methylene chain also similarly modify fibronectin, but with a stoichiometry of only about 0.3-0.4 per subunit. The spin-labeled primary amine with a trimethylene chain does not label fibronectin. The labeling site appears to be the glutamine-3 residue at the amino-terminal region of fibronectin. Electron spin resonance studies show that the bound labels are partially immobilized with an effective rotational correlation time of 0.4-0.6 ns. The spin-labeled primary amine with tetramethylene chain also is shown to covalently incorporate into bee venom melittin in the presence of guinea-pig liver transglutaminase. The syntheses of the various spin-labeled primary amines and their applications in the study of structure and dynamics of different proteins and peptides are discussed. The observations from this study suggest that these spin-labeled primary amines have potentially wide application as structural probes. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0006

文献信息

• In the Search for New Anticancer Drugs: 28. Synthesis and Evaluation of Highly Active Aminoxyl Labeled Amino Acid Derivatives Containing the [N;‐(2‐chloroethyl)‐N′‐nitrosoamino]carbonyl group
  作者：George Sosnovsky、Mustafa Baysal、Ercin Erciyas

  DOI：10.1002/jps.2600830715

  日期：1994.7

  The aminoxyl (nitroxyl) labeled (2-chloroethyl)nitrosocarbamoyl (CNC) derivatives of amino acids, i.e., N-[[N'-(2-chloroethyl)-N'-nitrosoamino]carbonyl]-A-(1-oxy-2,2,6,6- tetramethylpiperidin-4-yl)amides, A = glycyl (10a), A = L-alanyl (10b), A = L-valyl (10c), A = L-phenylalanyl (10d), were synthesized and evaluated in vitro for their anticancer activities against the murine lymphocytic leukemia P388

  氨基酸（即N-[[N'-（2-氯乙基）-N'-亚硝基氨基]羰基] -A-（1-氧基-）的氨基甲苯基（硝基）标记的（2-氯乙基）亚硝基氨基甲酰基（CNC）衍生物2,2,6,6-四甲基哌啶-4-基）酰胺，A =甘氨酰基（10a），A = L-丙氨酰基（10b），A = L-戊酰基（10c），A = L-苯丙氨酰基（10d），合成并体外评估它们对鼠淋巴细胞性白血病P388的抗癌活性。化合物10a-d的活性寿命增加242％至456％（％ILS）。在30天后，所有以12 mg / kg /天的高活性化合物10b和10c治疗9天的CDF1雄性小鼠均存活。然后针对小鼠淋巴白血病L1210体内测试化合物10a-d。在第60天，化合物10a-d的％ILS分别为496、663、663和581。60天后，所有以12 mg / kg /天的高活性化合物10b和10c治疗9天的CDF1雄性小鼠均存活。使用UV法测定