3-aminoacetophenone thiosemicarbazone | 87743-92-8

• 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: 3-aminoacetophenone thiosemicarbazone
• 英文别名: 1-(3-aminophenyl)ethylidenethiosemicarbazide；m-Amino-acetophenon-thiosemicarbazon；1-(3-amino-phenyl)-ethanone thiosemicarbazone；1-(3-Amino-phenyl)-aethanon-thiosemicarbazon；[1-(3-Aminophenyl)ethylideneamino]thiourea
• CAS: 87743-92-8
• 化学式: C₉H₁₂N₄S
• mdl: MFCD24388265
• 分子量: 208.287
• InChiKey: FJCDJOPKILSQQC-UHFFFAOYSA-N

物化性质

• 熔点：
  184-186 °C
• 沸点：
  403.2±47.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  间氨基苯乙酮 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3-aminoacetophenone thiosemicarbazone
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates

  摘要：

  The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Ttypanosoma cruzi in in vitro assays (IC50 < 57 mu M), and no mutagenic profile was observed in micro-nucleous tests. Although the in vitro inhibition test showed that 10-mu M doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.022

文献信息

• Structure-based modification of 3-/4-aminoacetophenones giving a profound change of activity on tyrosinase: From potent activators to highly efficient inhibitors
  作者：Ao You、Jie Zhou、Senchuan Song、Guoxun Zhu、Huacan Song、Wei Yi

  DOI：10.1016/j.ejmech.2015.02.013

  日期：2015.3

  In this study, we developed 3-/4-aminoacetophenones and their structure-based 3-/4-aminophenylethylidenethiosemicarbazide derivatives, respectively, as novel tyrosinase activators and inhibitors. Notably, all the obtained thiosemicarbazones displayed more potent tyrosinase inhibitory activities than kojic acid. Especially, compound 7k was found to be the most active tyrosinase inhibitor with IC50 value of 0.291 mu M. The structure-activity relationships (SARs) analysis showed that: (1) the amine group was absolutely necessarily for determining the tyrosinase activation activity; (2) the introduction of thiosemicarbazide group played a very vital role in transforming tyrosinase activators into tyrosinase inhibitors; (3) the phenylethylenethiosemicarbazide moiety was crucial for determining the tyrosinase inhibitory activity; (4) the type of acyl group had no obvious effect on the inhibitory activity; (5) the position of amide substituent on the phenyl ring influenced the tyrosinase inhibitory potency. Moreover, the inhibition mechanism and inhibition kinetics study revealed that compound 7k was reversible and non-competitive inhibitor, and compound 8h was reversible and competitive-uncompetitive mixed-II type inhibitor. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Witek, Stanislaw; Bielawski, Jacek; Bielawska, Alicja, Polish Journal of Chemistry, 1981, vol. 55, # 12, p. 2589 - 2600
  作者：Witek, Stanislaw、Bielawski, Jacek、Bielawska, Alicja

  DOI：——

  日期：——
• Pandeya; Aggarwal; Jain, Pharmazie, 1999, vol. 54, # 4, p. 300 - 302
  作者：Pandeya、Aggarwal、Jain

  DOI：——

  日期：——
• Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates
  作者：Lorena Blau、Renato Farina Menegon、Gustavo H.G. Trossini、João Vitor Dutra Molino、Drielli Gomes Vital、Regina Maria Barretto Cicarelli、Gabriela Duó Passerini、Priscila Longhin Bosquesi、Chung Man Chin

  DOI：10.1016/j.ejmech.2013.04.022

  日期：2013.9

  The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Ttypanosoma cruzi in in vitro assays (IC50 < 57 mu M), and no mutagenic profile was observed in micro-nucleous tests. Although the in vitro inhibition test showed that 10-mu M doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity. (C) 2013 Elsevier Masson SAS. All rights reserved.