5-(3,4-二甲氧基苯基)-4-乙基-4H-1,2,4-噻唑-3-硫醇 | 122772-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(3,4-二甲氧基苯基)-4-乙基-4H-1,2,4-噻唑-3-硫醇
• 中文别名: 5-(3,4-二甲氧基-苯基)-4-乙基-4H-[1,2,4]三唑-3-硫醇；5-(3,4-二甲氧苯基)-4-乙基-2H-1,2,4-三唑-3-硫酮；5-(3,4-二甲氧苯基)-4-乙基-2,4-二氢-3H-1,2,4-三唑-3-硫酮；5-(3,4-二甲氧苯基)-4-乙基-4H-1,2,4-三唑-3-硫醇
• 英文名称: 5-(3,4-dimethoxyphenyl)-4-ethyl-2,4-dihydro-[1,2,4]triazol-3-thione
• 英文别名: 5-(3,4-dimethoxyphenyl)-4-ethyl-4H-1,2,4-triazole-3-thiol；3-(3,4-dimethoxyphenyl)-4-ethyl-1H-1,2,4-triazole-5-thione
• CAS: 122772-20-7
• 化学式: C₁₂H₁₅N₃O₂S
• mdl: MFCD02046335
• 分子量: 265.336
• InChiKey: VNNWZCWDOJBXTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  179-182 °C(Solv: ethanol (64-17-5))
• 沸点：
  357.5±52.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-(3,4-二甲氧基苯基)-4-乙基-4H-1,2,4-噻唑-3-硫醇 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-(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：

  2-(3,4-dimethoxybenzoyl)-N-ethylhydrazinecarbothioamide 在 sodium hydroxide 、 盐酸 作用下， 生成 5-(3,4-二甲氧基苯基)-4-乙基-4H-1,2,4-噻唑-3-硫醇
  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).
• 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：——
• US5489598A
  申请人：——

  公开号：US5489598A

  公开（公告）日：1996-02-06