4-(4-hydroxy-1-naphthylamino)benzoic acid | 934844-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(4-hydroxy-1-naphthylamino)benzoic acid
• 英文别名: 4-[(4-Hydroxy-1-naphthyl)amino]benzoic acid；4-[(4-hydroxynaphthalen-1-yl)amino]benzoic acid
• CAS: 934844-92-5
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: VFTOUQCEUQBIES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基-1-萘胺 在 palladium diacetate 、 三溴化硼 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 39.0h， 生成 4-(4-hydroxy-1-naphthylamino)benzoic acid
  参考文献：
  名称：

  Design, Synthesis, and Structure–Activity Relationship of N-Arylnaphthylamine Derivatives as Amyloid Aggregation Inhibitors

  摘要：

  Dyes like CR are able to inhibit the aggregation of A beta fibrils. Thus, a screening of a series of dyes including ABBB (1) was performed. Its main component 2 tested in an in vitro assay (i.e., ThT assay) showed good potency at inhibiting fibrils association. Congeners 4-9 have been designed and synthesized as inhibitors of A beta aggregation. A nurnber of these newly synthesized compounds have been found to be active in the ThT assay with IC50 of 1-57.4 mu M. The most potent compound of this series, 4k, showed micromolar activity in this test. Another potent derivative 4q (IC50 = 5.6 mu M) rapidly crossed the blood-brain barrier, achieving whole brain concentrations higher than in plasma. So 4q could be developed to find novel potent antiaggregating beta A agents useful in Alzheimer disease as well as other neurological diseases characterized by deposits of amyloid aggregates.

  DOI：

  10.1021/jm301105m

文献信息

• Naphthyl Derivatives as Inhibitors of Beta-Amyloid Aggregation
  申请人：Minetti Patrizia

  公开号：US20080255232A1

  公开（公告）日：2008-10-16

  Compounds useful in the treatment of disorders characterized by deposits of amyloid aggregates are herein described together with pharmaceutical compounds containing the same. In particular the compounds of the present invention are those having the Formula (I) as reported below, where the radicals have the meaning indicated in the description.

  本文描述了用于治疗由淀粉样聚集物沉积所特征化的疾病的化合物，以及含有相同化合物的药物化合物。特别是，本发明的化合物是具有下面报告的式（I）的化合物，其中基团具有描述中所示的含义。
• Chemoenzymatic Synthesis of Phenol Diarylamine Using Non-Heme Diiron <i>N</i>-Oxygenase
  作者：Yuan-Yang Guo、Ze-Hua Tian、Luying Wang、Zheng-De Lai、Lingjun Li、Yong-Quan Li

  DOI：10.1021/acscatal.2c05190

  日期：2023.1.20

  Diarylamines are important moieties in organic materials and bioactive molecules. The traditional synthetic approach to diarylamines is metal catalysis in organic solvents. Herein, we report the chemoenzymatic synthesis of phenol diarylamines. Non-heme diiron N-oxygenase AzoC, which catalyzes the oxidization of amines to nitroso groups for azoxymycin biosynthesis in Streptomyces chattanoogensis, is

  二芳基胺是有机材料和生物活性分子中的重要组成部分。二芳基胺的传统合成方法是有机溶剂中的金属催化。在此，我们报告了苯酚二芳基胺的化学酶促合成。非血红素二铁N-加氧酶 AzoC，它催化胺氧化成亚硝基，用于查塔努生链霉菌中的阿霉素生物合成, 被设计为催化剂。这种合成方法可耐受多种苯酚和苯胺底物。机理研究表明，酶促形成的亚硝基中间体与苯氧化物偶联，促进了非酶促二芳基胺的合成。我们的研究表明，二芳基胺可以在水溶液中酶促合成，并突出了非血红素二铁N -加氧酶的合成潜力。
• NAPHTHYL DERIVATIVES AS INHIBITORS OF BETA-AMYLOID AGGREGATION
  申请人：SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP1937243A2

  公开（公告）日：2008-07-02
• [EN] NAPHTHYL DERIVATIVES INHIBITORS OF THE BETA-AMYLOID AGGREGATION<br/>[FR] DERIVES DE NAPHTYLE INHIBITEURS DE L'AGREGATION DE BETA-AMYLOIDE
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2007045593A2

  公开（公告）日：2007-04-26

  [EN] Compounds useful in the treatment of disorders characterised by deposits of amyloid aggregates are herein described together with pharmaceutical compounds containing the same. In particular the compounds of the present invention are those having the Formula (I) as reported below. where the radicals have the meaning indicated in the description.
  [FR] L'invention concerne des composés que l'on utilise dans le traitement de troubles se caractérisant par des dépôts d'agrégats d'amyloïdes, ainsi que de composés pharmaceutiques les contenant. Plus précisément, les composés selon l'invention sont ceux de la formule ci-dessous, où les radicaux ont la signification indiquée dans le descriptif.
• Design, Synthesis, and Structure–Activity Relationship of <i>N</i>-Arylnaphthylamine Derivatives as Amyloid Aggregation Inhibitors
  作者：Roberto Di Santo、Roberta Costi、Giuliana Cuzzucoli Crucitti、Luca Pescatori、Federica Rosi、Luigi Scipione、Diana Celona、Mario Vertechy、Orlando Ghirardi、Paola Piovesan、Mauro Marzi、Silvio Caccia、Giovanna Guiso、Fabrizio Giorgi、Patrizia Minetti

  DOI：10.1021/jm301105m

  日期：2012.10.11

  Dyes like CR are able to inhibit the aggregation of A beta fibrils. Thus, a screening of a series of dyes including ABBB (1) was performed. Its main component 2 tested in an in vitro assay (i.e., ThT assay) showed good potency at inhibiting fibrils association. Congeners 4-9 have been designed and synthesized as inhibitors of A beta aggregation. A nurnber of these newly synthesized compounds have been found to be active in the ThT assay with IC50 of 1-57.4 mu M. The most potent compound of this series, 4k, showed micromolar activity in this test. Another potent derivative 4q (IC50 = 5.6 mu M) rapidly crossed the blood-brain barrier, achieving whole brain concentrations higher than in plasma. So 4q could be developed to find novel potent antiaggregating beta A agents useful in Alzheimer disease as well as other neurological diseases characterized by deposits of amyloid aggregates.