6-Hydroxy-2, 5,7, 8-tetramethyl-chroman-2-carboxylic acid (2-amino-ethyl)-amide | 387335-93-5

• 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: 6-Hydroxy-2, 5,7, 8-tetramethyl-chroman-2-carboxylic acid (2-amino-ethyl)-amide
• 英文别名: AE-Trolox；Alkylperoxyradical probe；N-(2-aminoethyl)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide
• CAS: 387335-93-5
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: MKCFEDVUAXSJFS-UHFFFAOYSA-N

物化性质

• 熔点：
  164-165 °C
• 沸点：
  541.2±50.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-2, 5,7, 8-tetramethyl-chroman-2-carboxylic acid (2-amino-ethyl)-amide 在 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 6.0h， 生成 6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid [2-(6,8-dimercapto-octanoylamino)-ethyl]-amide
  参考文献：
  名称：

  Novel Potent Inhibitors of Lipid Peroxidation with Protective Effects against Reperfusion Arrhythmias

  摘要：

  A series of new compounds that contain lipoic acid and trolox connected through spacers were synthesized and examined for their antioxidant activity and their protective effects against reperfusion arrhythmias in isolated heart preparations. All compounds tested are strong inhibitors of lipid peroxidation. in rat liver microsomal membranes induced by ferrous ions and ascorbate. N-(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-N'-(1,2-dithiolane-3-pentanoyl)-1,2-phenylenediamine (13) exhibits anti-lipid peroxidation activity at the nanomolar range. N-(3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonyl)-N'-(1,2-dithiolane-3-pentanoyl)ethylenediamine (10) and 13 totally suppressed reperfusion arrhythmias.

  DOI：

  10.1021/jm010962w
• 作为产物：
  描述：

  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 、 二氯甲烷 为溶剂， 生成 6-Hydroxy-2, 5,7, 8-tetramethyl-chroman-2-carboxylic acid (2-amino-ethyl)-amide
  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

• LUMINESCENT SQUARAINE ROTAXANE COMPOUNDS
  申请人：SETA BioMedicals, LLC

  公开号：US20190048196A1

  公开（公告）日：2019-02-14

  Luminescent reporter compounds that are rotaxanes having the structure where B—Z—C is a reporter molecule based on a squaraine type molecule, or similar reporter, and K is a macrocycle that encircles and interlocks with the reporter molecule. Applications of the reporter compounds are provided, as well as reactive intermediates used to synthesize the reporter compounds, and methods of synthesizing the reporter compounds.

  具有如下结构的发光报告化合物，是一种轮烷： 其中B—Z—C是基于方酸染料类型分子或类似报告分子的报告分子，K是一个环绕并与报告分子互锁的大环。报告化合物的应用被提供，以及用于合成报告化合物的反应中间体，以及合成报告化合物的方法。
• Chroman/Catechol Hybrids:  Synthesis and Evaluation of Their Activity against Oxidative Stress Induced Cellular Damage
  作者：Maria Koufaki、Elissavet Theodorou、Dimitrios Galaris、Lambros Nousis、Efrosini S. Katsanou、Michael N. Alexis

  DOI：10.1021/jm0506120

  日期：2006.1.1

  chromans substituted at positions 2 or 5 by catechol derivatives were synthesized, and their activity against oxidative stress induced cellular damage was studied. Specifically, the ability of the new molecules to protect cultured cells from H(2)O(2)-induced DNA damage was evaluated using single cell gel electrophoresis (comet assay), while the neuroprotective activity of the new compounds against oxidative

  合成了三类在邻苯二酚衍生物在2或5位取代的苯并二氢吡喃，并研究了它们对氧化应激诱导的细胞损伤的活性。具体来说，使用单细胞凝胶电泳（彗星试验）评估了新分子保护培养的细胞免受H（2）O（2）诱导的DNA损伤的能力，而新化合物针对氧化应激诱导的神经保护活性被编程使用谷氨酸-challanged海马HT22细胞研究了细胞死亡。大多数新化合物比槲皮素具有更强的神经保护作用。5-取代的苯并二氢吡喃类似物，例如咖啡酰胺12和16和二氢二苯乙烯类似物24，分别对Jurkat T细胞和HT22细胞中H（2）O（2）-和谷氨酸诱导的损伤最有效。
• The intramolecular self-healing strategy applied to near infrared fluorescent aminotricarbocyanines
  作者：Javier M. Abbas、Martín Stortz、Hernán B. Rodríguez、Valeria Levi、Alejandro Wolosiuk、Carla C. Spagnuolo

  DOI：10.1016/j.dyepig.2020.109040

  日期：2021.2

  fluorophore core. The synthesized dyes also include a functional group (-COOH) in their chemical structure for further (bio)conjugation of the fluorescent probe to biomolecules or surfaces. The photostability of the dyes was investigated spectroscopically in cuvette experiments as well as microscopically in dye embedded PMMA films. The rigid heptamethine modified dyes show enhanced photostability in

  我们目前的三种新型近红外（NIR）氨基三甲基花青衍生物与自包含的抗氧化剂部分，没食子酸和6-羟基-2,5,7,8-四甲基苯并吡喃-2-羧酸（Trolox）的合成和光物理研究。这项工作的目的是将分子内自我修复策略应用于水溶性氨基三甲基花青素，以探索将抗氧化剂部分直接连接至荧光团核心的作用。合成染料的化学结构中还包含一个官能团（-COOH），用于将荧光探针进一步（生物）偶联到生物分子或表面。在比色杯实验中用光谱法对染料的光稳定性进行了研究，在嵌入了染料的PMMA膜中用显微镜进行了研究。
• 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。
• Luminescent squaraine rotaxane compounds
  申请人：SETA BioMedicals, LLC

  公开号：US11091646B2

  公开（公告）日：2021-08-17

  Luminescent reporter compounds that are rotaxanes having the structure where B—Z—C is a reporter molecule based on a squaraine type molecule, or similar reporter, and K is a macrocycle that encircles and interlocks with the reporter molecule. Applications of the reporter compounds are provided, as well as reactive intermediates used to synthesize the reporter compounds, and methods of synthesizing the reporter compounds.

  发光报告化合物是具有以下结构的轮烷化合物 其中，B-Z-C 是基于方碱类分子或类似荧光体的荧光体分子，K 是环绕荧光体分子并与之互锁的大环。本文提供了报告化合物的应用、用于合成报告化合物的反应中间体以及合成报告化合物的方法。