N-ethyl-2-[(4-methoxyphenyl)carbonyl]hydrazinecarbothioamide | 505064-97-1

• 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: N-ethyl-2-[(4-methoxyphenyl)carbonyl]hydrazinecarbothioamide
• 英文别名: 1-ethyl-3-[(4-methoxybenzoyl)amino]thiourea
• CAS: 505064-97-1
• 化学式: C₁₁H₁₅N₃O₂S
• 分子量: 253.325
• InChiKey: JBARFDFYKOYIFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  94.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-ethyl-2-[(4-methoxyphenyl)carbonyl]hydrazinecarbothioamide 在 三乙胺 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 生成 2-[4-ethyl-5-(4-methoxyphenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-1-phenyl-ethanone
  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：

  茴香酸乙酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 N-ethyl-2-[(4-methoxyphenyl)carbonyl]hydrazinecarbothioamide
  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

• 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 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.
• 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
  作者：Muhammad Arfan、Sabahat Zahra Siddiqui、Muhammad Athar Abbasi、Aziz-ur-Rehman、Syed Muhammad Saad、Syed Adnan Ali Shah、Muhammad Ashraf、Safdar Hussain、Farman Ali、Mehwish Solangi、Khalid Mohammed Khan

  DOI：10.1007/s13738-023-02756-3

  日期：——

  Neurodegeneration is an unfortunate condition associated with the steady loss of structures and functions of neurons. The most common complication that arises from neurodegenerative disorder is Alzheimer’s disease, which occurs due to hyperactivities of the responsible enzymes acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). We synthesized a series of medicinally important 1,2,4-triazole-3-ylthio-N-acetamides serving AChE and BChE inhibitors to cope with this stressful condition. The promising results were found, especially for the synthetic compound 2-((4-ethyl-5-(4′-methoxyphenyl)-4H-1,2,4-triazole-3-yl)thio)-N-(3′′,5′′-dimethyl phenyl)acetamide (8j) against AChE and 2-((4-ethyl-5-(4′-methoxyphenyl)-4H-1,2,4-triazole-3-yl)thio)-N-(3′′,4′′-dimethyl phenyl)acetamide (8i) against BChE, using eserine as standard. Molecular docking analyses were also performed to gain insight into the molecules’ interactions with the active sites of the enzymes. All the synthetic compounds were characterized by spectroscopic techniques such as 1H-NMR, 13C-NMR, FTIR, and EIMS.

  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-