2-hydroxy-5-(pyridin-3-yl)benzoic acid | 23380-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-hydroxy-5-(pyridin-3-yl)benzoic acid
• 英文别名: 5-(3-Pyridyl)salicylsaeure；5-(pyridin-3-yl)salicylic acid；2-hydroxy-5-pyridin-3-ylbenzoic acid
• CAS: 23380-76-9
• 化学式: C₁₂H₉NO₃
• 分子量: 215.208
• InChiKey: GJSFZMHGFSKOAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-(pyridin-3-yl)benzoic acid 在 N,N-二甲基甲酰胺 吡啶 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 methyl 2-(2-acetoxy-5-(pyridin-3-yl)benzamido)-4-(furan-2-yl)benzoate
  参考文献：
  名称：

  N-ACYL ANTHRANILIC ACID DERIVATIVE OR SALT THEREOF

  摘要：

  通用公式（1）表示的N-酰基蒽酸衍生物或其盐对预防或治疗与胶原蛋白过度产生相关的疾病具有用处。（在该公式中，R1代表羧基或类似物；R2代表氢原子或类似物；R3代表可选择取代的芳基或类似物；X1代表羰基；X2代表连接手；X3代表连接手；X4代表连接手或类似物；A代表可选择取代的苯基或类似物。）

  公开号：

  US20110275797A1
• 作为产物：
  描述：

  ethyl 2-hydroxy-5-(pyridin-3-yl)benzoate 在 lithium hydroxide monohydrate 作用下， 反应 12.0h， 以99%的产率得到2-hydroxy-5-(pyridin-3-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

• Structural Modifications of Salicylates: Inhibitors of Human CD81‐Receptor HCV‐E2 Interaction
  作者：Marcel Holzer、Sigrid Ziegler、Alexander Neugebauer、Bernd Kronenberger、Christian D. Klein、Rolf W. Hartmann

  DOI：10.1002/ardp.200700261

  日期：2008.8

  extracellular loop (LEL) of the CD81‐receptor (crystal structure: PDB‐ID: 1G8Q). After benzyl salicylate had been experimentally validated to be a moderate inhibitor of the CD81‐LEL–HCV‐E2 interaction, further optimization was performed and heterocyclic‐substituted benzyl salicylate derivatives were synthesized. The compounds were tested for their ability to inhibit the interaction of a fluorescence‐labeled

  本文的出发点是使用 CD81 受体（晶体结构：PDB-ID：1G8Q）的大细胞外环（LEL）的开放构象进行虚拟筛选的结果。在实验证实水杨酸苄酯是 CD81-LEL-HCV-E2 相互作用的温和抑制剂后，进行了进一步优化并合成了杂环取代的水杨酸苄酯衍生物。使用 HUH7.5 细胞测试了这些化合物抑制荧光标记抗体与 CD81-LEL 相互作用的能力。与水杨酸苄酯相比，没有化合物显示出抑制蛋白质-蛋白质相互作用的增加。
• N-acyl anthranilic acid derivative or salt thereof
  申请人：Yokotani Junichi

  公开号：US08492582B2

  公开（公告）日：2013-07-23

  The invention relates to an N-acyl anthranilic acid derivative or it's salt having collagen production inhibitory action.

  本发明涉及一种具有胶原蛋白生成抑制作用的N-酰基蒽酰氨酸衍生物或其盐。
• SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway
  作者：Hee-Don Chae、Nick Cox、Samanta Capolicchio、Jae Wook Lee、Naoki Horikoshi、Sharon Kam、Andrew A. Ng、Jeffrey Edwards、Tae-León Butler、Justin Chan、Yvonne Lee、Garrett Potter、Mark C. Capece、Corey W. Liu、Soichi Wakatsuki、Mark Smith、Kathleen M. Sakamoto

  DOI：10.1016/j.bmcl.2019.06.023

  日期：2019.8

  Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. We describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochemical properties relative to previously described derivatives of naphthol AS-E phosphate.
• US8492582B2
  申请人：——

  公开号：US8492582B2

  公开（公告）日：2013-07-23