6-(4-aminophenoxy)hexan-1-ol | 118619-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(4-aminophenoxy)hexan-1-ol
• 英文别名: 4-(6-hydroxyhexyloxy)aniline；6-(4-Aminophenoxy)hexan-1-ol
• CAS: 118619-11-7
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: AXIVXNZYOFGQKT-UHFFFAOYSA-N

物化性质

• 沸点：
  381.4±22.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-aminophenoxy)hexan-1-ol 在 2-甲基苯磺酸 、 hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 6-(6-Hydroxyhexoxy)quinoline-2,4-dicarboxylic acid
  参考文献：
  名称：

  Synthesis and in Vitro Pharmacology of Substituted Quinoline-2,4-dicarboxylic Acids as Inhibitors of Vesicular Glutamate Transport

  摘要：

  The vesicular glutamate transport (VGLUT) system selectively mediates the uptake of L-glutamate into synaptic vesicles. Uptake is linked to an H+-ATPase that provides coupling among ATP hydrolysis, an electrochemical proton gradient, and glutamate transport. Substituted quinoline-2,4-dicarboxylic acids (QDCs), prepared by condensation of dimethyl keto-glutaconate (DKG) with substituted anilines and subsequent hydrolysis, were investigated as potential VGLUT inhibitors in synaptic vesicles. A brief panel of substituted QDCs was previously reported (Carrigan et al. Bioorg. Med. Chem. Lett. 1999, 9, 2607-2612), and showed that certain substituents led to more potent competitive inhibitors of VGLUT. Using these compounds as leads, an expanded series of QDC analogues were prepared either by condensation of DKG with novel anilines or via aryl-coupling (Suzuki or Heck) to dimethyl 6-bromoquino-linedicarboxylate. From the panel of almost 50 substituted QDCs tested as inhibitors of the VGLUT system, the 6-PhCH=CH-QDC (K-i = 167 muM), 6-PhCH2CH2-QDC (K-i = 143 muM), 6-(4'-phenylstyryl)-QDC (K-i = 64 AM), and 6-biphenyl-4-yl-QDC (K-i = 41 muM) were found to be the most potent blockers. A preliminary assessment of the key elements needed for binding to the VGLUT protein based on the structure-activity relationships for the panel of substituted QDCs is discussed herein. The substituted QDCs represent the first synthetically derived VGLUT inhibitors and are promising templates for the development of selective transporter inhibitors.

  DOI：

  10.1021/jm010261z
• 作为产物：
  描述：

  6-氯-1-己醇 在 盐酸 、 potassium carbonate 、 sodium iodide 作用下， 以 丙醇 、 丙酮 为溶剂， 反应 48.0h， 生成 6-(4-aminophenoxy)hexan-1-ol
  参考文献：
  名称：

  合成具有三氮烯连接基的聚合物载体的新策略

  摘要：

  描述了基于使用二乙胺三氮烯来稳定和生成聚合物负载的重氮离子的新策略。描述了四种新的经济合成方法，该方法合成了具有3和6个碳原子间隔基和衍生自间氨基和对氨基苯酚的三氮烯连接基的四种新型聚合物载体，并将其与传统方法进行了比较。显示了聚合物结合的三氮烯掩蔽的重氮盐作为固定仲胺（降冰片和4-哌啶酮及其酯化和氧化）的载体以及作为胺清除剂的可能应用。对meta -C 3 -T2和para -C 3的新支持-T2接头显示出较高的负载量，通常可使产物具有良好的收率和纯度。

  DOI：

  10.1016/j.tet.2003.10.091

文献信息

• [EN] MITOCHONDRIA-TARGETED DICARBONYL SEQUESTERING COMPOUNDS<br/>[FR] COMPOSÉS DE SÉQUESTRATION DE GROUPES DICARBONYLES CIBLANT LES MITOCHONDRIES
  申请人：MEDICAL RES COUNCIL

  公开号：WO2015075200A1

  公开（公告）日：2015-05-28

  The invention relates to compounds having Formula (1): A-L-B or pharmaceutically acceptable salts thereof, wherein: A is a dicarbonyl sequestering moiety comprising a substituted aryl group or a substituted heteroaryl group; L is an optional linker moiety; and B is a mitochondrial targeting moiety. The invention also relates to pharmaceutical compositions containing such compounds and salts, and to the use of such compounds and salts for treating diabetes, preferably hyperglycaemic diabetes. A mass spectrometry probe and to a method of labelling a biological molecule 1 for mass spectrometry detection are also described.

  该发明涉及具有Formula（1）的化合物：A-L-B或其药用盐，其中：A是包含取代芳基或取代杂环芳基的二羰基螯合基团；L是可选的连接基团；B是线粒体靶向基团。该发明还涉及含有这种化合物和盐的药物组合物，以及利用这种化合物和盐治疗糖尿病，尤其是高血糖糖尿病的用途。还描述了一种质谱探针和一种用于质谱检测生物分子的标记方法。
• 一种可Diels-Alder加成反应偶氮苯单体的制备方法及应用
  申请人：常州大学

  公开号：CN110343079B

  公开（公告）日：2022-05-17

  本发明属于高分子材料技术领域，具体涉及一种可Diels‑Alder加成反应偶氮苯单体的制备方法及应用，通过对硝基苯酚的醚化、硝基还原、重氮偶合和酯化等多步反应获得偶氮苯单体：MA‑FAzo。单体MA‑FAzo经自由基均聚反应，制备含Diels‑Alder加成结构的偶氮苯聚合物PAzo。再将含马来酰亚胺结构的壳聚糖与偶氮苯聚合物PAzo进行复合，壳聚糖中的马来酰亚胺结构与呋喃偶氮苯单元形成可逆的含Diels‑Alder加成结构，制备出壳聚糖‑PAzo复合膜，基于呋喃/马来酰亚胺之间的热可逆DA反应在交联的聚合物体系中，解交联程度更高，并且可以多次循环利用，更利于聚合物的回收再利用。
• A new route to medium and large heterocyclic compounds
  作者：Tina Ventrice、Eva M. Campi、W. Roy Jackson、Antonio F. Patti

  DOI：10.1039/a904168k

  日期：——

  Hydrogenation of nitrobenzenes bearing aldehyde-containing substituents over heterogeneous platinum or palladium catalysts gives medium and/or large heterocyclic amines as a result of simple or dimeric cyclisation in moderate to good yields; a range of heteroatoms can be incorporated into the macrocycles, enhancing their potential as ligands.

  在异相铂或钯催化剂作用下，含醛基取代基的硝基苯氢化，可生成中等或大环杂环胺，这是简单或二聚环化的结果，产率中等或较高；多种杂原子可结合到大环中，从而增强其作为配体的潜力。
• A mitochondria-targeted mass spectrometry probe to detect glyoxals: implications for diabetes
  作者：Pamela Boon Li Pun、Angela Logan、Victor Darley-Usmar、Balu Chacko、Michelle S. Johnson、Guang W. Huang、Sebastian Rogatti、Tracy A. Prime、Carmen Methner、Thomas Krieg、Ian M. Fearnley、Lesley Larsen、David S. Larsen、Katja E. Menger、Yvonne Collins、Andrew M. James、G.D. Kishore Kumar、Richard C. Hartley、Robin A.J. Smith、Michael P. Murphy

  DOI：10.1016/j.freeradbiomed.2013.11.025

  日期：2014.2

  The glycation of protein and nucleic acids that occurs as a consequence of hyperglycemia disrupts cell function and contributes to many pathologies, including those associated with diabetes and aging. Intracellular glycation occurs after the generation of the reactive 1,2-dicarbonyls methylglyoxal and glyoxal, and disruption of mitochondrial function is associated with hyperglycemia. However, the contribution of these reactive dicarbonyls to mitochondrial damage in pathology is unclear owing to uncertainties about their levels within mitochondria in cells and in vivo. To address this we have developed a mitochondria-targeted reagent (MitoG) designed to assess the levels of mitochondrial dicarbonyls within cells. MitoG comprises a lipophilic triphenylphosphonium cationic function, which directs the molecules to mitochondria within cells, and an o-phenylenediamine moiety that reacts with dicarbonyls to give distinctive and stable products. The extent of accumulation of these diagnostic heterocyclic products can be readily and sensitively quantified by liquid chromatography-tandem mass spectrometry, enabling changes to be determined. Using the MitoG-based analysis we assessed the formation of methylglyoxal and glyoxal in response to hyperglycemia in cells in culture and in the Akita mouse model of diabetes in vivo. These findings indicated that the levels of methylglyoxal and glyoxal within mitochondria increase during hyperglycemia both in cells and in vivo, suggesting that they can contribute to the pathological mitochondrial dysfunction that occurs in diabetes and aging. (C) 2013 The Authors. Published by Elsevier Inc. All rights reserved.
• Preparation and Characterization of Crosslinked Azobenzene Liquid-Crystalline Polymer Fibers
  作者：Taiki Yoshino、Jun-ichi Mamiya、Motoi Kinoshita、Tomiki Ikeda、Yanlei Yu

  DOI：10.1080/15421400701681083

  日期：2007.12.14