5-(3,4-dimethoxybenzyl)-4-phenyl-4H-1,2,4-triazole-3-thiol | 91759-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3,4-dimethoxybenzyl)-4-phenyl-4H-1,2,4-triazole-3-thiol
• 英文别名: 3-(3,4-dimethoxyphenyl)-4-phenyl-1H-1,2,4-triazole-5-thione
• CAS: 91759-69-2
• 化学式: C₁₆H₁₅N₃O₂S
• mdl: MFCD00617761
• 分子量: 313.38
• InChiKey: VWQIHWAMQDBWDM-UHFFFAOYSA-N

物化性质

• 熔点：
  234-235 °C(Solv: ethanol (64-17-5))
• 沸点：
  430.2±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3,4-dimethoxybenzyl)-4-phenyl-4H-1,2,4-triazole-3-thiol 在 sodium hydroxide 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 2-(5-(3,4-dimethoxyphenyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)acetic acid
  参考文献：
  名称：

  5-芳基-2H-四唑，5-芳基-2H-四唑-2-乙酸和[（4-苯基-5-芳基-4H-1,2,4-三唑-3-基）硫代]的合成乙酸可能是超氧化物清除剂和抗炎药。

  摘要：

  一系列5-芳基-2H-四唑，5-芳基-2H-四唑-2-乙酸和[（4-苯基-5-芳基-4H-1,2,4-三唑-3-基）硫代合成乙酸，并在体外进行角叉菜胶诱导的大鼠爪水肿测定和反向被动Arthus反应中的超氧化物清除活性测试。羟基取代的化合物可以有效地用作超氧化物的体外清除剂，但不能有效地用作体内抗炎剂。

  DOI：

  10.1021/jm00378a007
• 作为产物：
  描述：

  2-(3,4-dimethoxybenzoyl)-N-phenylhydrazinecarbothioamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 生成 5-(3,4-dimethoxybenzyl)-4-phenyl-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  1-[(1R, 2S)-2-氟环丙基]环丙沙星-1,2,4-三唑-5(4H)-硫酮杂化物的设计、合成和抗菌评价

  摘要：

  设计、合成和评估了一类新的 1-[(1R,2S)-2-氟环丙基]环丙沙星 (CPFX)-1,2,4-三唑-5(4H)-硫酮杂化物 6a-6o对一组临床上重要的药物敏感和耐药革兰氏阳性和革兰氏阴性病原体的抗菌活性。我们的结果表明，所有杂种 6a - 6o 对受试菌株，尤其是革兰氏阴性病原体具有很强的效力。合成的杂合体比亲本 1-[(1R,2S)-2-氟环丙基]CPFX (1) 更有效，并且与 CPFX 和左氧氟沙星对大多数测试病原体的作用相当，值得进一步研究。

  DOI：

  10.1002/cbdv.201800261

文献信息

• Pathak; Devani; Shishoo, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1, p. 83 - 86
  作者：Pathak、Devani、Shishoo、Shah

  DOI：——

  日期：——
• New nitric oxide donating 1,2,4-triazole/oxime hybrids: Synthesis, investigation of anti-inflammatory, ulceroginic liability and antiproliferative activities
  作者：Mohamed Abdel-Aziz、Gamal El-Din A.A. Abuo-Rahma、Eman A.M. Beshr、Taha F.S. Ali

  DOI：10.1016/j.bmc.2013.04.022

  日期：2013.7

  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.
• 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).
• 1,2,4-Triazole/oxime hybrids as new strategy for nitric oxide donors: Synthesis, anti-inflammatory, ulceroginicity and antiproliferative activities
  作者：Gamal El-Din A.A. Abuo-Rahma、Mohamed Abdel-Aziz、Eman A.M. Beshr、Taha F.S. Ali

  DOI：10.1016/j.ejmech.2013.11.006

  日期：2014.1

  A series of novel nitric oxide (NO) donating triazole/oxime hybrids was prepared and evaluated for their anti-inflammatory activity and antiproliferative 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 ketone intermediates and indomethacin. The NO-donating oximes 7i and 7k achieved remarkable cell growth inhibition activity against most of the tested cell lines. Compound 7k was found to be with high selectivity against CNS subpanel with selectivity ratio of 11.99 at GI(50) level. (C) 2013 Elsevier Masson SAS. All rights reserved.
• New 1,2,4-triazole-Chalcone hybrids induce Caspase-3 dependent apoptosis in A549 human lung adenocarcinoma cells
  作者：Fatma F. Ahmed、Amer Ali Abd El-Hafeez、Samar H. Abbas、Dalia Abdelhamid、Mohamed Abdel-Aziz

  DOI：10.1016/j.ejmech.2018.03.073

  日期：2018.5

  A series of novel 1, 2, 4-triazole/ichalcone hybrids was prepared and identified with different spectroscopic techniques. The prepared compounds showed remarkable cytotoxic activity against different cancer cell lines. Compounds 24, 25, 27, 41 and 47 had shown the highest cytotoxicity among the tested compounds against human lung adenocarcinoma A549 cells with IC50 ranging from 4.4 to 16.04 mu M compared to cisplatin with IC50 of 153 mu M. Flow cytometric analysis of the tested compounds showed an increase in the number of apoptotic cells in a dose-dependent manner. The further mechanistic study demonstrated that 1, 2, 4-triazole-chalcone hybrids induced apoptosis via increased level of proapoptotic protein Bax, release of cytochrome c from mitochondria and activation of caspase-3/8/9 proteins. However, general caspase inhibition by the pan-caspase inhibitor, z-VAD-fmk, significantly decreased the apoptosis induced by the tested hybrids, suggesting dependency of apoptosis on activation of the caspase-3 pathway. (C) 2018 Elsevier Masson SAS. All rights reserved.