3-[3-[(4-methoxyphenyl)disulfanyl]-1H-1,2,4-triazol-5-yl]pyridine | 1393829-55-4

• 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: 3-[3-[(4-methoxyphenyl)disulfanyl]-1H-1,2,4-triazol-5-yl]pyridine
• CAS: 1393829-55-4
• 化学式: C₁₄H₁₂N₄OS₂
• 分子量: 316.407
• InChiKey: CGZQOPQNWPTCBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[3-[(4-methoxyphenyl)disulfanyl]-1H-1,2,4-triazol-5-yl]pyridine 、 乙酸酐 反应 0.5h， 以87%的产率得到1-(3-((4-methoxyphenyl)disulfanyl)-5-(pyridin-3-yl)-1H-1,2,4-triazol-1-yl)ethanone
  参考文献：
  名称：

  发现不对称的芳香族二硫化物作为SARS-CoV主蛋白酶的新型抑制剂：化学合成，生物学评估，分子对接和3D-QSAR研究

  摘要：

  2003年，世界范围内的严重急性呼吸道综合症（SARS）爆发导致了很高的死亡率。SARS相关冠状病毒（SARS-CoV）的主要蛋白酶（M pro）是发现用于治疗这种威胁生命的疾病的药物的重要靶标。在筛选新的抗SARS药物的过程中，我们发现一系列不对称的芳香族二硫化物首次显着抑制了SARS-CoV M pro。本文中，化学合成了40种新型不对称芳族二硫化物，并在体外评估了它们对SARS-CoV M pro的生物学活性。这些新型化合物显示出优异的IC 50数据范围为0.516–5.954μM。初步研究表明，这些二硫化物是可逆的和竞争性抑制剂。通过分子对接模拟生成了可能的结合模式，并构建了一个比较场分析（CoMFA）模型来理解结构-活性关系。因此，本研究为设计和鉴定具有全新化学结构的抗SARS药物提供了有意义的指导。

  DOI：

  10.1016/j.ejmech.2017.05.045
• 作为产物：
  描述：

  4-methoxybenzenesulfenyl chloride 、 5-(3-吡啶基)-4H-1,2,4-三唑-3-硫醇 以 乙醚 为溶剂， 反应 5.0h， 生成 3-[3-[(4-methoxyphenyl)disulfanyl]-1H-1,2,4-triazol-5-yl]pyridine
  参考文献：
  名称：

  Synthesis, Crystal Structure, in Vitro Acetohydroxyacid Synthase Inhibition, in Vivo Herbicidal Activity, and 3D-QSAR of New Asymmetric Aryl Disulfides

  摘要：

  Acetohydroxyacid synthase (AHAS; EC 2.2.1.6) is an important bioactive target for the design environmentally:., benign herbicides. On the basis of previous virtual screening, 50 asymmetric aryl disulfides containing [1,2,4]triazole groups were synthesized and characterized by H-1 NMR, HRMS, and crystal structure. Compounds I-a, I-b, and I-p show K-i values of 1.70, 4.69, and 5.57 mu M, respectively, for Wild type Arabidopsis thaliana AHAS (AtAHAS) and low resistance, against mutant type AtAHAS W574L. At 100 mg L-1 concentration, compounds. I-a, II-a, and II-b exhibit 86.6, 817, and 87.5% in vivo rape root growth inhibition. CoMFA steric and electrostatic contour maps were established, and a possible binding mode was suggested from molecular docking, which :provide valuable information to understand the key structural features. of these disulfide compounds. To the authors knowledge, this is the first comprehensive case suggesting that asymmetric aryl disulfides are novel AHAS inhibitors.

  DOI：

  10.1021/jf302206x

文献信息

• Discovery of unsymmetrical aromatic disulfides as novel inhibitors of SARS-CoV main protease: Chemical synthesis, biological evaluation, molecular docking and 3D-QSAR study
  作者：Li Wang、Bo-Bo Bao、Guo-Qing Song、Cheng Chen、Xu-Meng Zhang、Wei Lu、Zefang Wang、Yan Cai、Shuang Li、Sheng Fu、Fu-Hang Song、Haitao Yang、Jian-Guo Wang

  DOI：10.1016/j.ejmech.2017.05.045

  日期：2017.9

  outbreak of severe acute respiratory syndrome (SARS) in 2003 had caused a high rate of mortality. Main protease (Mpro) of SARS-associated coronavirus (SARS-CoV) is an important target to discover pharmaceutical compounds for the therapy of this life-threatening disease. During the course of screening new anti-SARS agents, we have identified that a series of unsymmetrical aromatic disulfides inhibited SARS-CoV

  2003年，世界范围内的严重急性呼吸道综合症（SARS）爆发导致了很高的死亡率。SARS相关冠状病毒（SARS-CoV）的主要蛋白酶（M pro）是发现用于治疗这种威胁生命的疾病的药物的重要靶标。在筛选新的抗SARS药物的过程中，我们发现一系列不对称的芳香族二硫化物首次显着抑制了SARS-CoV M pro。本文中，化学合成了40种新型不对称芳族二硫化物，并在体外评估了它们对SARS-CoV M pro的生物学活性。这些新型化合物显示出优异的IC 50数据范围为0.516–5.954μM。初步研究表明，这些二硫化物是可逆的和竞争性抑制剂。通过分子对接模拟生成了可能的结合模式，并构建了一个比较场分析（CoMFA）模型来理解结构-活性关系。因此，本研究为设计和鉴定具有全新化学结构的抗SARS药物提供了有意义的指导。
• Synthesis, Crystal Structure, in Vitro Acetohydroxyacid Synthase Inhibition, in Vivo Herbicidal Activity, and 3D-QSAR of New Asymmetric Aryl Disulfides
  作者：Jun Shang、Wei-Min Wang、Yong-Hong Li、Hai-Bin Song、Zheng-Ming Li、Jian-Guo Wang

  DOI：10.1021/jf302206x

  日期：2012.8.29

  Acetohydroxyacid synthase (AHAS; EC 2.2.1.6) is an important bioactive target for the design environmentally:., benign herbicides. On the basis of previous virtual screening, 50 asymmetric aryl disulfides containing [1,2,4]triazole groups were synthesized and characterized by H-1 NMR, HRMS, and crystal structure. Compounds I-a, I-b, and I-p show K-i values of 1.70, 4.69, and 5.57 mu M, respectively, for Wild type Arabidopsis thaliana AHAS (AtAHAS) and low resistance, against mutant type AtAHAS W574L. At 100 mg L-1 concentration, compounds. I-a, II-a, and II-b exhibit 86.6, 817, and 87.5% in vivo rape root growth inhibition. CoMFA steric and electrostatic contour maps were established, and a possible binding mode was suggested from molecular docking, which :provide valuable information to understand the key structural features. of these disulfide compounds. To the authors knowledge, this is the first comprehensive case suggesting that asymmetric aryl disulfides are novel AHAS inhibitors.