4-allyl-5-(3,4-dimethoxyphenyl)-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-allyl-5-(3,4-dimethoxyphenyl)-4H-1,2,4-triazole-3-thiol
• 英文别名: 3-(3,4-dimethoxyphenyl)-4-prop-2-enyl-1H-1,2,4-triazole-5-thione
• 化学式: C₁₃H₁₅N₃O₂S
• mdl: MFCD00617762
• 分子量: 277.347
• InChiKey: JCRDSESGVZXDSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  4-allyl-5-(3,4-dimethoxyphenyl)-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-allyl-5-(3,4-dimethoxyphenyl)-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：

  藜芦酸 在 硫酸 、 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-allyl-5-(3,4-dimethoxyphenyl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  1,2,4-Triazole/oxime hybrids as new strategy for nitric oxide donors: Synthesis, anti-inflammatory, ulceroginicity 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 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.

  DOI：

  10.1016/j.ejmech.2013.11.006

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：——
• 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).
• 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.
• PATHAK, U. S.;DEVANI, M. B.;SHISHOO, C. J.;SHAH, S., INDIAN J. CHEM. B, 28,(1989) N, C. 83-86
  作者：PATHAK, U. S.、DEVANI, M. B.、SHISHOO, C. J.、SHAH, S.

  DOI：——

  日期：——