4-ethyl-5-(4-methoxy-phenyl)-4H-[1,2,4]triazole-3-thiol

• 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-ethyl-5-(4-methoxy-phenyl)-4H-[1,2,4]triazole-3-thiol
• 英文别名: 4-ethyl-5-(4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol；4-ethyl-3-(4-methoxyphenyl)-1H-1,2,4-triazole-5-thione
• 化学式: C₁₁H₁₃N₃OS
• mdl: MFCD01164029
• 分子量: 235.31
• InChiKey: NAIPWRRJIAVUOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethyl-5-(4-methoxy-phenyl)-4H-[1,2,4]triazole-3-thiol 在 盐酸羟胺 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 2-[4-ethyl-5-(4-methoxyphenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-1-phenylethanone oxime
  参考文献：
  名称：

  New nitric oxide donating 1,2,4-triazole/oxime hybrids: Synthesis, investigation of anti-inflammatory, ulceroginic liability and antiproliferative activities

  摘要：

  A series of novel nitric oxide (NO) donating triazole/oxime hybrids was prepared and evaluated for their anti-inflammatory activity. Most of the tested compounds showed significant anti-inflammatory activity using carrageenan-induced rat paw edema method compared to indomethacin. Calculation of the ulcer indices and histopathological investigation indicated that the prepared NO-donating oximes exhibited less ulcerogenicity compared to their intermediate ketones and indomethacin. The NO-donating oxime 6i revealed significant activity against renal cancer A498 cell lines with 50.52 cell growth inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.022
• 作为产物：
  描述：

  对甲氧基苯甲酰肼 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.33h， 生成 4-ethyl-5-(4-methoxy-phenyl)-4H-[1,2,4]triazole-3-thiol
  参考文献：
  名称：

  Innovative cholinergic scaffolds, synthesis, and characterization of substituted 1,2,4-triazole-3-ylthio-N-acetamides and their in silico studies: supplement against neurodegenerative disease

  摘要：

  神经退化是一种不幸的疾病，与神经元的结构和功能的持续丧失有关。神经退化性疾病最常见的并发症是阿尔茨海默氏症，这种疾病是由于负责的酶乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的过度活动引起的。我们合成了一系列重要的1,2,4-三唑-3-基硫代-N-乙酰胺，作为乙酰胆碱酯酶和丁酰胆碱酯酶的抑制剂，以应对这种压力。使用乙酰胆碱作为标准，我们发现了一些有希望的结果，特别是针对乙酰胆碱酯酶的合成化合物2-((4-乙基-5-(4′-甲氧基苯基)-4H-1,2,4-三唑-3-基)硫代)-N-(3′′,5′′-二甲基苯基)乙酰胺（8j）和针对丁酰胆碱酯酶的合成化合物2-((4-乙基-5-(4′-甲氧基苯基)-4H-1,2,4-三唑-3-基)硫代)-N-(3′′,4′′-二甲基苯基)乙酰胺（8i）。我们还进行了分子对接分析，以了解分子与酶活性位点的相互作用。所有合成化合物的特征都是通过光谱技术，如1H-NMR、13C-

  DOI：

  10.1007/s13738-023-02756-3

文献信息

• Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
  申请人：Edwards Louise

  公开号：US20050272779A1

  公开（公告）日：2005-12-08

  The present invention relates to new compounds of formula I, to pharmaceutical formulations containing the compounds, and to the use of the compounds in the prevention and/or treatment of mGluR5 receptor-mediated disorders.

  本发明涉及公式I的新化合物，包含该化合物的药物配方，以及利用该化合物预防和/或治疗mGluR5受体介导的疾病的用途。
• Compounds
  申请人：Arora Jalaj

  公开号：US20060122397A1

  公开（公告）日：2006-06-08

  The present invention relates to new compounds of formula I, a process for their preparation and new intermediates prepared therein, pharmaceutical formulations containing said compounds and to the use of said compounds in therapy.

  本发明涉及化合物I的新化合物，其制备过程和其中制备的新中间体，含有该化合物的制药配方以及在治疗中使用该化合物的用途。
• ADDITIONAL HETEROPOLYCYCLIC COMPOUNDS AND THEIR USE AS METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS
  申请人：Edwards Louise

  公开号：US20080045571A1

  公开（公告）日：2008-02-21

  The present invention relates to new compounds of formula I, to pharmaceutical formulations containing the compounds, and to the use of the compounds in the prevention and/or treatment of mGluR5 receptor-mediated disorders.

  本发明涉及公式I的新化合物，包括含有该化合物的制药配方，以及该化合物在预防和/或治疗mGluR5受体介导的疾病中的使用。
• Derivatives of 2-(1,2,4-triazol-3-ylsulfanyl)-N-1,3,4-thiadiazol-2-yl acetamide which are useful for the treatment of inter alia diabetes
  申请人：APOGLYX AB

  公开号：US10011597B2

  公开（公告）日：2018-07-03

  Disclosed are compounds, pharmaceutical compositions and methods for modulating aquaporin 9.

  所公开的是调节水蒸气素 9 的化合物、药物组合物和方法。
• Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity
  作者：Hamada H.H. Mohammed、El-Shimaa M.N. Abdelhafez、Samar H. Abbas、Gamal A.I. Moustafa、Glenn Hauk、James M. Berger、Satoshi Mitarai、Masayoshi Arai、Rehab M. Abd El-Baky、Gamal El-Din A. Abuo-Rahma

  DOI：10.1016/j.bioorg.2019.102952

  日期：2019.7

  New N-4-piperazinyl ciprofloxacin-triazole hybrids 6a-o were prepared and characterized. The in vitro antimycobacterial activity revealed that compound 6a experienced promising antimycobacterial activity against Mycobactrium smegmatis compared with the reference isoniazide (INH). Additionally, compound 6a exhibited broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative bacteria compared with the reference ciprofloxacin. Also, compounds 6g and 6i displayed considerable antifungal activity compared with the reference ketoconazole. DNA cleavage assay of the highly active compounds 6c and 6h showed a good correlation between the Mycobactrium cleaved DNA gyrase assay and their in vitro antimycobactrial activity. Moreover, molecular modeling studies were done for the designed ciprofloxacin derivatives to predict their binding modes towards Topoisomerase II enzyme (PDB: 5bs8).