(E)-2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-(p-tolyl)hydrazinecarbothioamide | 97724-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-(p-tolyl)hydrazinecarbothioamide
• 英文别名: 3,4-Methylendioxy-benzaldehyd-(4-p-tolyl-thiosemicarbazon)；benzo[1,3]dioxole-5-carbaldehyde 4-p-tolyl-thiosemicarbazone；piperonal-(4-p-tolyl thiosemicarbazone)；Piperonal-(4-p-tolyl-thiosemicarbazon)；1-[(E)-1,3-benzodioxol-5-ylmethylideneamino]-3-(4-methylphenyl)thiourea
• CAS: 97724-22-6
• 化学式: C₁₆H₁₅N₃O₂S
• 分子量: 313.38
• InChiKey: ZMRFYGWNINETGN-RQZCQDPDSA-N

物化性质

• 熔点：
  199 °C
• 沸点：
  457.7±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-(p-tolyl)hydrazinecarbothioamide 、 2-溴丙酸 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 benzo[1,3]dioxole-5-carbaldehyde (5-methyl-4-oxo-3-p-tolyl-thiazolidin-2-ylidene)-hydrazone
  参考文献：
  名称：

  Shah,I.D.; Trivedi,J.P., Journal of the Indian Chemical Society, 1963, vol. 40, p. 889 - 893

  摘要：

  DOI：
• 作为产物：
  描述：

  4-4-甲苯基-3-胺基硫脲 在 乙醇 作用下， 生成 (E)-2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-(p-tolyl)hydrazinecarbothioamide
  参考文献：
  名称：

  4-substituierte Thiosemicarbazide als Reagentien zur Charakterisierung von Aldehyden und Ketonen

  摘要：

  DOI：

  10.1007/bf00535377

文献信息

• Synthetic thiosemicarbazones as a new class of Mycobacterium tuberculosis protein tyrosine phosphatase A inhibitors
  作者：Larissa Sens、Ana Caroline Arruda de Souza、Lucas Antonio Pacheco、Angela Camila Orbem Menegatti、Mattia Mori、Alessandra Mascarello、Ricardo José Nunes、Hernán Terenzi

  DOI：10.1016/j.bmc.2018.10.030

  日期：2018.11

  Mycobacterium tuberculosis secretes two protein tyrosine phosphatases as virulence factors, PtpA and PtpB. Inhibition studies of these enzymes have shown significant attenuation of the M. tuberculosis growth in vivo. As PtpA mediates many effects on the regulation of host signaling ensuring the intracellular survival of the bacterium we report, for the first time, thiosemicarbazones as potential novel

  结核分枝杆菌分泌两种蛋白酪氨酸磷酸酶作为致病因子，PTPA和PtpB。对这些酶的抑制研究显示出体内结核分枝杆菌生长的显着减弱。由于PTPA介导了对宿主信号传导调控的许多影响，从而确保了细菌的细胞内存活，我们首次报道了硫代半脲酮作为潜在的新型PTPA抑制剂。合成了几种化合物并进行了生物学评估，得出有趣的结果。酶的动力学分析表明，化合物5，9和18是PTPA的非竞争性抑制剂，与ķ我值范围从1.2到5.6 µM。建模研究阐明了体外观察到的构效关系，并指出了PTPA结构中可能存在的变构结合位点。据我们所知，这是有力的非竞争性PTPA抑制剂的首次公开，其在未来研究和开发类似物方面具有巨大潜力。
• Synthesis, Antioxidant Activity, Acetylcholinesterase Inhibition and Quantum Studies of Thiosemicarbazones
  作者：Larissa Sens、Aldo de Oliveira、Alessandra Mascarello、Inês Brighente、Rosendo Yunes、Ricardo Nunes

  DOI：10.21577/0103-5053.20170146

  日期：——

  Thiosemicarbazones are a class of compounds of interest for Medicinal Chemistry, as they are structurally diverse and have numerous biological activities reported in the literature. This study describes the synthesis of seventeen thiosemicarbazones, which were investigated as potential therapeutic agents for the treatment of Alzheimer's disease through antioxidant tests and an inhibitory assay of the acetylcholinesterase enzyme. All compounds showed excellent inhibition of acetylcholinesterase and exhibited excellent antioxidant action when compared to the standards. In addition, a quantum study was carried out, in which the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energy values of each compound were obtained. From these theoretical data, chemical properties were calculated and correlated with the experimental data.