2-hydroxy-5-(naphthalen-1-yl)benzoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-5-(naphthalen-1-yl)benzoic acid
• 英文别名: 2-Hydroxy-5-(naphthalen-1-yl)benzoic acid；2-hydroxy-5-naphthalen-1-ylbenzoic acid
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: REHHUONKBGIXRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-碘水杨酸 在 四(三苯基膦)钯 、 lithium hydroxide monohydrate 、 硫酸 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 43.0h， 生成 2-hydroxy-5-(naphthalen-1-yl)benzoic acid
  参考文献：
  名称：

  Bi-aryl Analogues of Salicylic Acids: Design, Synthesis and SAR Study to Ameliorate Endoplasmic Reticulum Stress

  摘要：

  Introduction: Endoplasmic reticulum (ER) stress condition is characterized as the accumulation of misfolded or unfolded proteins in lumen of ER. This condition has been implicated in various diseases and pathologies including β-cell apoptosis, Alzheimer's disease and atherosclerosis. We have reported that hydroxynaphthoic acids (HNA), naphthalene analogues of salicylic acid (SA), reduced ER stress. In this study, we explored structural modification to bi-aryl analogues of SA. Methods: Palladium-catalyzed cross-coupling was applied to synthesize bi-aryl analogues of SA. Anti-ER stress activity was monitored by using our cell-based assay system where ER stress is induced by tunicamycin. To monitor ER stress markers, ER stress was induced physiologically relevant palmitate system. Results: Many analogues decreased ER stress signal induced by tunicamycin. Compounds creating dihedral angle between Ar group and SA moiety generally increased the activity but gave some cytotoxicity to indicate the crucial role of flat conformation of aromatic region. The best compound (16e) showed up to almost 6-fold and 90-fold better activity than 3-HNA and tauro-ursodeoxycholic acid, positive controls, respectively. ER stress markers such as p-PERK and p-JNK were accordingly decreased in Western blotting upon treatment of 16e under palmitate-induced condition. Conclusion: Anti-ER stress activity and toxicity profile of bi-aryl analogues of SA could provide a novel platform for potential therapy for protein misfolding diseases.

  DOI：

  10.2147/dddt.s319287

文献信息

• Diflunisal Derivatives as Modulators of ACMS Decarboxylase Targeting the Tryptophan–Kynurenine Pathway
  作者：Yu Yang、Timothy Borel、Francisco de Azambuja、David Johnson、Jacob P. Sorrentino、Chinedum Udokwu、Ian Davis、Aimin Liu、Ryan A. Altman

  DOI：10.1021/acs.jmedchem.0c01762

  日期：2021.1.14

  quinolinic acid, the precursor for de novo biosynthesis of nicotinamide adenine dinucleotide (NAD+). In a competing reaction, ACMS is decarboxylated by ACMS decarboxylase (ACMSD) for further metabolism and energy production. Therefore, the inhibition of ACMSD increases NAD+ levels. In this study, an Food and Drug Administration (FDA)-approved drug, diflunisal, was found to competitively inhibit ACMSD.

  在色氨酸降解的犬尿氨酸途径中，一种不稳定的代谢中间体 α-氨基-β-羧基粘康酸-ε-半醛 (ACMS) 可以非酶环化形成喹啉酸，这是从头生物合成烟酰胺腺嘌呤二核苷酸 (NAD + )的前体. 在竞争反应中，ACMS 被 ACMS 脱羧酶 (ACMSD) 脱羧，以进一步代谢和产生能量。因此，抑制 ACMSD 会增加 NAD +水平。在这项研究中，发现食品和药物管理局 (FDA) 批准的药物二氟尼柳可竞争性抑制 ACMSD。ACMSD 与二氟尼柳的复杂结构揭示了一种以前未知的配体结合模式，并且与抑制测定的结果以及构效关系 (SAR) 研究一致。此外，两种合成的二氟尼柳衍生物的半数最大抑制浓度 (IC 50 ) 值分别比二氟尼柳高 1 个数量级，分别为 1.32 ± 0.07 μM ( 22 ) 和 3.10 ± 0.11 μM ( 20 )。结果表明二氟尼柳衍生物具有调节 NAD +水平。这里
• METHOD OF PRODUCING AROMATIC AMINO COMPOUNDS
  申请人：Yokoyama Norimasa

  公开号：US20110257404A1

  公开（公告）日：2011-10-20

  [Problem] To provide a method of producing an aromatic amino compound by using a primary or secondary amine compound and a halogenated aromatic compound as starting materials, and relying upon the Ullmann reaction, the method being capable of obtaining the highly pure aromatic amino compound in high yields and inexpensively. [Means for Solution] A method of producing an aromatic amino compound by using a primary or secondary amine compound having an aromatic ring group and a halogenated aromatic compound as starting materials, reacting the amine compound with the halogenated aromatic compound in the presence of a copper catalyst and a base so as to produce the aromatic amino compound having a structure in which an aromatic ring group derived from the halogenated aromatic compound is coupled to the amino group of the amine compound, wherein the amine compound and the halogenated aromatic compound are reacted together under a condition where an aromatic oxycarboxylic acid having a hydroxyl group and a hydroxycarbonyl group that are bonded to neighboring carbon atoms, is made present together with the copper catalyst and the base.

  提供一种通过使用一种主要或次要胺化合物和一种卤代芳香化合物作为起始原料，依靠乌尔曼反应来生产芳香氨基化合物的方法，该方法能够以高产率和低成本获得高纯度的芳香氨基化合物。 通过使用具有芳香环基团的主要或次要胺化合物和一种卤代芳香化合物作为起始原料，在铜催化剂和碱的存在下将胺化合物与卤代芳香化合物反应，从而产生具有芳香环基团从卤代芳香化合物衍生的结构的芳香氨基化合物，其中胺化合物和卤代芳香化合物在存在具有羟基和羟基羰基团结合到相邻碳原子的芳香氧羧酸的条件下与铜催化剂和碱一起反应。
• AROMATIC AMINO COMPOUND MANUFACTURING METHOD
  申请人：Hodogaya Chemical Co., Ltd.

  公开号：EP2394980B1

  公开（公告）日：2016-12-21
• US8735626B2
  申请人：——

  公开号：US8735626B2

  公开（公告）日：2014-05-27
• US9238624B2
  申请人：——

  公开号：US9238624B2

  公开（公告）日：2016-01-19