4-ethyl-1-(3,4,5-trimethoxy-benzoyl)-thiosemicarbazide | 29246-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-ethyl-1-(3,4,5-trimethoxy-benzoyl)-thiosemicarbazide
• 英文别名: N-ethyl-2-[(3,4,5-trimethoxyphenyl)carbonyl]hydrazinecarbothioamide；1-ethyl-3-[(3,4,5-trimethoxybenzoyl)amino]thiourea
• CAS: 29246-90-0
• 化学式: C₁₃H₁₉N₃O₄S
• 分子量: 313.378
• InChiKey: WPMPZHWPJZYUSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-ethyl-1-(3,4,5-trimethoxy-benzoyl)-thiosemicarbazide 在 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 2-[4-ethyl-5-(3,4,5-trimethoxyphenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-N-[4-(1-hydroxyiminoethyl)phenyl]acetamide
  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
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 4-ethyl-1-(3,4,5-trimethoxy-benzoyl)-thiosemicarbazide
  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

文献信息

• An investigation of supramolecular synthons in 1,2,4-triazole-3(4H)-thione compounds. X-ray crystal structures, energetic and Hirshfeld surface analysis
  作者：Aamer Saeed、Zaman Ashraf、Humaira Nadeem、Jim Simpson、Hiram Pérez、Mauricio F. Erben

  DOI：10.1016/j.molstruc.2019.06.049

  日期：2019.11

  Abstract A series of four closely related 1,2,4-triazole-3-thione (1-4) compounds was obtained by heterocyclization of thiosemicarbazides under basic catalytic conditions. The crystal structures of the 4-alkyl-5-(substituted-phenyl)-2H-1,2,4-triazole-3(4H)-thione derivatives [4-alkyl = 4-ethyl-5-phenyl (1), 4-hexyl-5-phenyl (2), 4-hexyl-5-p-tolyl (3), and 4-ethyl-5-(2,4,6-trimethoxyphenyl) (4)] have

  摘要 通过氨基硫脲在碱性催化条件下的杂环化反应，得到了一系列密切相关的4个1,2,4-三唑-3-硫酮(1-4)化合物。4-烷基-5-(取代-苯基)-2H-1,2,4-三唑-3(4H)-硫酮衍生物的晶体结构[4-烷基=4-乙基-5-苯基(1), 4-己基-5-苯基(2)、4-己基-5-对甲苯基(3)和4-乙基-5-(2,4,6-三甲氧基苯基)(4)]已被测定。PIXEL 晶格能量计算表明色散分量做出了主要贡献，而库仑项也对总能量做出了显着贡献。涉及 N–H⋯S=C 氢键的反转二聚体的相互作用能表明库仑能量分量对堆积稳定性的主要贡献。Hirshfeld 表面和 2D 指纹图使我们能够可视化不同的分子间接触及其对每种化合物总表面的相对贡献。晶体堆积和能量特征的综合分析证明了 (···HNCS)2 型 R 2 2 ( 8 ) 超分子合成子在这些 1,2,4-三唑-的固态结构中的关键作用3-硫酮。
• 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).
• Mazzone; Bonina; Reina, Farmaco, Edizione Scientifica, 1981, vol. 36, # 3, p. 181 - 196
  作者：Mazzone、Bonina、Reina、Blandino

  DOI：——

  日期：——
• Mazzone; Bonina; Puglisi, Farmaco, Edizione Scientifica, 1982, vol. 37, # 10, p. 685 - 700
  作者：Mazzone、Bonina、Puglisi、Arrigo、Cosentino、Blandino

  DOI：——

  日期：——
• 1,3,4-THIADIAZOLES. REGIOSELECTIVE <i>O</i>-DEMETHYLATION ON DEHYDRATIVE CYCLIZATION OF 1-(3,4,5-TRIMETHOXYBENZOYL)4-SUBSTITUTED THIOSEMICARBAZIDES WITH SULPHURIC ACID
  作者：Mohamed Al-Omar、Omar A. Al-Deeb、Hamad A. Al-Khamees、Ali A. El-Emam

  DOI：10.1080/10426500490485525

  日期：2004.12.1

  Cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-substituted thiosemicarbazides 2a-g with sulphuric acid at ambient temperature afforded the selectively demethylated products 2-(4-hydroxy-3,5-dimethoxyphenyl)5-substituted amino-1,3,4-thiodiazoles 4a-g. Meanwhile, dehydrative cyclization of 1-(3,4,5-trimethoxybenzoyl)-4-(benzyl or t-butyl)thiosemicarbazides 2h,i with sulphuric acid yielded 2-(4-hydroxy-3,5-dimethoxyphenyl)-5-amino-1,3,4-thiadiazole 5. On the other hand, dehydration of 2h,i by heating with phosphorus oxychloride yielded 2-(3,4,5-trimethoxyphenyl)-5-amino-1,3,4-thiadiazole 6.