4-[3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzenesulfonamide
• 英文别名: 4-[3,5-Bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzenesulfonamide；4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzenesulfonamide
• 化学式: C₂₀H₁₆N₄O₄S
• 分子量: 408.437
• InChiKey: BYRYHMHOVAQOOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  水杨酰胺 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 为溶剂， 反应 3.0h， 生成 4-[3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis of 1,3,5-triphenyl-1,2,4-triazole derivatives and their neuroprotection by anti-oxidative stress and anti-inflammation and protecting BBB

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115742

文献信息

• [EN] PREPARATION OF NOVEL DEFERASIROX ANALOGUES FOR ANTIMALARIAL ACTIVITY<br/>[FR] PRÉPARATION DE NOUVEAUX ANALOGUES DU DÉFÉRASIROX POUR UNE ACTIVITÉ ANTIPALUDIQUE
  申请人：HAVALDAR FREDDY H

  公开号：WO2016203488A1

  公开（公告）日：2016-12-22

  The present invention relates to processes for the preparation of novel deferasirox analogues for antimalarial activity. The present invention further provides process for synthesis of novel deferasirox analogues.

  本发明涉及制备新型去铁医药物deferasirox的类似物，以用于抗疟活性。本发明还提供了制备新型deferasirox类似物的合成过程。
• [3,5-二取代苯基-1-(1,2,4-三氮唑基)]苯磺酸衍生物及制备方法和应用
  申请人：中山大学

  公开号：CN110357824A

  公开（公告）日：2019-10-22

  本发明公开了一种[3,5‑二取代苯基‑1‑(1,2,4‑三氮唑基)]苯磺酸衍生物及其制备方法和应用。以取代苯甲酸原料，通过酰化反应及与取代苯甲酰胺的缩合成环反应，再与对肼基苯磺酸衍生物反应得到目标产物[3,5‑二取代苯基‑1‑(1,2,4‑三氮唑基)]苯磺酸衍生物。该类化合物可有效对抗由双氧水、硝普钠、铁离子、铜离子引起的神经细胞氧化应激损伤，通过清除自由基和恢复线粒体膜电位修复线粒体功能，对神经元细胞表现出具有显著的保护作用。该类化合物清除自由基和靶向保护线粒体的神经保护作用，可应用于制备预防和治疗中风、脑损伤、脊髓损伤、帕金森病、阿尔兹海默症、肌萎缩侧索硬化症等神经退行性疾病的药物。
• Synthesis and biological evaluation of 1,2,4-triazole derivatives as potential neuroprotectant against ischemic brain injury
  作者：Liping Liao、Caibao Jiang、Jianwen Chen、Jinguo Shi、Xinhua Li、Yang Wang、Jin Wen、Shujia Zhou、Jie Liang、Yaoqiang Lao、Jingxia Zhang

  DOI：10.1016/j.ejmech.2020.112114

  日期：2020.3

  A series of 1,2,4-triazole derivatives 1-14 was synthesized to investigate their neuroprotective effects and mechanisms of action. Compounds 5-11 noticeably protected PC12 cells from the cytotoxicity of H2O2 or sodium nitroprusside (SNP). Compound 11 was the most effective derivative. Compound 11 chelated Fe (II) iron, scavenged reactive oxygen species (ROS), and restored the mitochondrial membrane potential (MMP). Moreover, it enhanced the activity of the antioxidant defense system by increasing the serum level of superoxide dismutase (SOD) and promoting the nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2). Compound 11 caused certain improvements in behavior, the cerebral infarction area, and serum levels of biochemical indicators (TNF-alpha, IL-10, SOD and MDA) in a rat MCAO model. The lethal dose (LD50) of compound 11 in mice receiving intraperitoneal injections was greater than 400 mg/kg. Meanwhile, pharmacokinetic experiments revealed high bioavailability of this compound after both oral and intravenous administration (F = 60.76%, CL = 0.014 mg/kg/h) and a longer half-life (4.26 and 5.11 h after oral and intravenous administration, respectively). Based on these findings, compound 11 may be a promising neuroprotectant for the treatment of ischemic stroke. (C) 2020 Elsevier Masson SAS. All rights reserved.