NHS-Trolox | 784143-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: NHS-Trolox
• 英文别名: N-hydroxysuccinimidyl trolox ester；(2,5-Dioxopyrrolidin-1-yl) 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylate；(2,5-dioxopyrrolidin-1-yl) 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylate
• CAS: 784143-45-9
• 化学式: C₁₈H₂₁NO₆
• 分子量: 347.368
• InChiKey: UPJFEZNOBLTQLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  NHS-Trolox 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid {2-[2-(5-[1,2]dithiolan-3-yl-pentanoylamino)-ethylamino]-ethyl}-amide
  参考文献：
  名称：

  Synthesis of chroman analogues of lipoic acid and evaluation of their activity against reperfusion arrhythmias

  摘要：

  Novel hybrids of lipoic acid and trolox connected through triamine spacers as well as analogues in which the lipoic acid was attached at different positions of the chroman moiety of vitamin E through an amide bond, were synthesized and exhibited strong inhibition of the microsomal lipid peroxidation. Moreover, the new molecules, at 1 muM concentration, reduced reperfusion arrhythimas and MDA content on isolated rat heart preparations, with the 2- and 5-subtituted chromans possessing the better cardioprotective activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.012
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 奎诺二甲基丙烯酸酯 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 生成 NHS-Trolox
  参考文献：
  名称：

  Antioxidants Based on Covalently and Ionically Bound Trolox Conjugates

  摘要：

  合成了三种类型的 trolox 二聚体（双-trolox 衍生物），其中两种是通过具有共价或离子键的乙二胺连接体对称结合的 trolox 分子对，其中一种是不对称离子-共价缀合物。测量了合成化合物的水溶性和抗氧化活性。

  DOI：

  10.1007/s10600-015-1494-2

文献信息

• Covalent and Ionic Conjugates of Trolox and α-Tocopherol with 1-Aminoadamantane
  作者：Yu. V. Yushkova、S. V. Morozov、E. I. Chernyak、I. A. Grigor’ev

  DOI：10.1007/s10600-017-2201-2

  日期：2017.11

  Covalent, ionic, and ionic-covalent conjugates of trolox and α-tocopherol with 1-aminoadamantane were synthesized. Their structures were elucidated using mass spectrometry and IR, PMR, and 13C NMR spectroscopy. The water solubility of the ionic trolox conjugates with 1-aminoadamantane increased by 2–24 times as compared with that of trolox whereas that of the α-tocopherol succinate conjugates remained the same as that of α-tocopherol.

  共价、离子以及离子-共价结合型的trolox和α-生育酚与1-氨基金刚烷化合物已被合成。它们的结构通过质谱和红外、质子磁共振及13C核磁共振光谱得以阐明。与trolox相比，离子型trolox与1-氨基金刚烷的结合物在水中的溶解度提高了2至24倍，而α-生育酚琥珀酸结合物的水溶性则与α-生育酚相同。
• TETRACYCLINE COMPOUNDS FOR TREATING NEURODEGENERATIVE DISORDERS
  申请人：PARATEK PHARMACEUTICALS, INC.

  公开号：US20150174144A1

  公开（公告）日：2015-06-25

  Tetracycline compounds for treating neurodegenerative disorders are disclosed herein. Also disclosed is a pharmaceutical composition comprising the tetracycline compounds, and a method for treating, preventing, or ameliorating neurodegenerative disorders or inflammation in a subject by administering the tetracycline compounds or a pharmaceutical composition thereof, either alone or in combination with a second therapeutic agent.

  本文披露了用四环素化合物治疗神经退行性疾病的方法。还披露了包含四环素化合物的药物组合物，以及通过给予四环素化合物或其药物组合物来治疗、预防或改善受试者的神经退行性疾病或炎症的方法，无论是单独使用还是与第二种治疗药物联合使用。
• Synthesis of a second generation chroman/catechol hybrids and evaluation of their activity in protecting neuronal cells from oxidative stress-induced cell death
  作者：Maria Koufaki、Elissavet Theodorou、Xanthippi Alexi、Michael N. Alexis

  DOI：10.1016/j.bmc.2010.04.042

  日期：2010.6.1

  A new generation of chroman/catechol hybrids bearing heterocyclic five-membered rings, such as 1,2, 4-oxadiazole 1,3,4-oxadiazole, 1,2,3-triazole, tetrazole and isoxazole, were designed and synthesized. The activity of the new derivatives against oxidative stress induced neuronal damage, was evaluated using glutamate-challenged hippocampal HT22 cells.Compound 3 in which a 3,4-dimethoxyphenyl moiety, is directly attached to the 1,2,4-oxadiazole ring was the most active among the 2-substituted chroman analogues, with EC50 = 254 +/- 65 nM. Concerning the 5-subtituted chroman analogues, isoxazole derivative 29 exhibited the strongest activity (EC50 = 245 +/- 38 nM). However, 29 was cytotoxic at concentrations higher than 1 mu M, while the triazole analogue 24 (EC50 = 801 +/- 229 nM), was non-toxic at all concentrations tested. (C) 2010 Elsevier Ltd. All rights reserved.
• [EN] TETRACYCLINE COMPOUNDS FOR TREATING NEURODEGENERATIVE DISORDERS<br/>[FR] COMPOSÉS TÉTRACYCLINE DESTINÉS À TRAITER DES TROUBLES NEURODÉGÉNÉRATIFS
  申请人：PARATEK PHARM INNC

  公开号：WO2014012094A3

  公开（公告）日：2014-03-06
• Synthesis of chroman analogues of lipoic acid and evaluation of their activity against reperfusion arrhythmias
  作者：Maria Koufaki、Anastasia Detsi、Elissavet Theodorou、Christina Kiziridi、Theodora Calogeropoulou、Athanasios Vassilopoulos、Angeliki P. Kourounakis、Eleni Rekka、Panos N. Kourounakis、Catherine Gaitanaki、Panagiota Papazafiri

  DOI：10.1016/j.bmc.2004.07.012

  日期：2004.9

  Novel hybrids of lipoic acid and trolox connected through triamine spacers as well as analogues in which the lipoic acid was attached at different positions of the chroman moiety of vitamin E through an amide bond, were synthesized and exhibited strong inhibition of the microsomal lipid peroxidation. Moreover, the new molecules, at 1 muM concentration, reduced reperfusion arrhythimas and MDA content on isolated rat heart preparations, with the 2- and 5-subtituted chromans possessing the better cardioprotective activity. (C) 2004 Elsevier Ltd. All rights reserved.