p-aminoacetophenonethiosemicarbazone | 7410-53-9

• 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: p-aminoacetophenonethiosemicarbazone
• 英文别名: 4-aminoacetophenone thiosemicarbazone；1-(4-aminophenyl)ethylidenethiosemicarbazide；4-Amino-acetophenon-thiosemicarbazon；Thiosemicarbazon d. 4-Amino-acetophenons；1-(4-amino-phenyl)-ethanone thiosemicarbazone；1-(4-Amino-phenyl)-aethanon-thiosemicarbazon；4-AAP-TSC；Hydrazinecarbothioamide, 2-[1-(4-aminophenyl)ethylidene]-；[1-(4-aminophenyl)ethylideneamino]thiourea
• CAS: 7410-53-9
• 化学式: C₉H₁₂N₄S
• 分子量: 208.287
• InChiKey: IKXKPKRBUBTOBD-UHFFFAOYSA-N

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

• 作为反应物：
  描述：

  p-aminoacetophenonethiosemicarbazone 在 氯化亚砜 作用下， 以69%的产率得到4-(4-aminophenyl)-1,2,3-thiadiazole-2(5H)-carbothioamide
  参考文献：
  名称：

  A New Type of Synthesis of 1,2,3-Thiadiazole and 1,2,3-Diazaphosphole Derivatives Via-Hurd-Mori Cyclization

  摘要：

  我们提出了一种简短高效的合成方法，从廉价且易得的樟脑和苯乙酮衍生物开始合成标题化合物。优化的步骤允许在几个步骤内大规模制备这种新型合成物。通过相应的半羧肼6-10，从酮1-5制备了新的1,2,3-噻二唑和1,2,3-二氮磷杂环衍生物11-20。分别使用了Hurd-Mori和Lalezari方法来制备这些1,2,3-噻二唑和1,2,3-二氮磷杂环衍生物。这些衍生物由于具有高潜在的生物活性，展现出抗癌效果。

  DOI：

  10.1155/2012/457949
• 作为产物：
  描述：

  4-氨基苯乙酮 、 氨基硫脲 以 乙醇 为溶剂， 反应 5.0h， 以95%的产率得到p-aminoacetophenonethiosemicarbazone
  参考文献：
  名称：

  A New Type of Synthesis of 1,2,3-Thiadiazole and 1,2,3-Diazaphosphole Derivatives Via-Hurd-Mori Cyclization

  摘要：

  我们提出了一种简短高效的合成方法，从廉价且易得的樟脑和苯乙酮衍生物开始合成标题化合物。优化的步骤允许在几个步骤内大规模制备这种新型合成物。通过相应的半羧肼6-10，从酮1-5制备了新的1,2,3-噻二唑和1,2,3-二氮磷杂环衍生物11-20。分别使用了Hurd-Mori和Lalezari方法来制备这些1,2,3-噻二唑和1,2,3-二氮磷杂环衍生物。这些衍生物由于具有高潜在的生物活性，展现出抗癌效果。

  DOI：

  10.1155/2012/457949

文献信息

• Microwave‐assisted synthesis and biological evaluation of new thiazolylhydrazone derivatives as tyrosinase inhibitors and antioxidants
  作者：Yu Zhang、Xi Fu、Yangting Yan、Jinbing Liu

  DOI：10.1002/jhet.3760

  日期：2020.3

  In this work, we have synthesized a series of 2‐thiazolylhydrazone derivatives (1–27) and investigated their biological activities as tyrosinase inhibitors and antioxidants. Some compounds showed potent tyrosinase inhibitory activities and 4‐(2‐(2‐(1‐(4‐Aminophenyl)ethylidene)‐hydrazinyl)thiazol‐4‐yl) phenol (26) showed more potent inhibitory effect than the standard tyrosinase inhibitor kojic acid

  在这项工作中，我们合成了一系列2-噻唑并hydr衍生物（1-27），并研究了它们作为酪氨酸酶抑制剂和抗氧化剂的生物学活性。一些化合物显示出强大的酪氨酸酶抑制活性，而4-（2-（2-（2-（1-（4-氨基苯基）亚乙基）-肼基）噻唑-4-基）苯酚（26）显示出比标准酪氨酸酶抑制剂曲酸更强的抑制作用。酸（IC 50：9.8μM对23.6μM）。化合物2，14，和26在2,2-二苯基-1-吡啶甲基肼基（DPPH）和2,2'-氮杂双（3-乙基苯并噻唑啉-6-磺酸）（ABTS）分析中显示出高抗氧化活性。结构-活性关系（SAR）表明，溴，羟基和氨基的取代对酪氨酸酶的抑制作用有很大影响。机理和动力学研究表明，化合物26作为可逆性和非竞争性抑制剂，对酪氨酸酶具有抑制作用。对接研究表明化合物26通过氢键与蘑菇酪氨酸酶强烈相互作用。
• Ruthenium(II) mediated C–H activation of substituted acetophenone thiosemicarbazones: Synthesis, structural characterization, luminescence and electrochemical properties
  作者：Rupesh Narayana Prabhu、Devaraj Pandiarajan、Rengan Ramesh

  DOI：10.1016/j.jorganchem.2009.09.010

  日期：2009.12

  solution all the complexes exhibit metal-to-ligand charge transfer transitions (MLCT) in the visible region and are emissive at room temperature with quantum yield of 0.001–0.005. The crystal structure of one of the complexes [Ru(4CAP-PTSC)(CO)(AsPh3)2] (4) has been solved by single crystal X-ray crystallography and it indicates the presence of a distorted octahedral geometry in these complexes. All the complexes

  在甲醇中用4'-取代的苯乙酮硫代半脲酮衍生物对[RuHCl（CO）（AsPh 3）3 ]进行甲醇回流处理，得到了一系列具有空气稳定性的，含有通式[Ru（L）（CO）的硫代氨基脲的新型钌（II）环化金属配合物。 ）（AsPh 3）2 ]。4'-取代的苯乙酮硫半脲配体表现为双阴离子的齿状C，N和S供体（L），并通过芳族碳，亚胺氮和硫醇硫与钌配位。通过元素分析和光谱方法（FT-IR，UV-Vis，11 H NMR，ESI-MS）和X射线晶体学。在氯仿溶液中，所有络合物在可见光区域均表现出金属至配体的电荷转移跃迁（MLCT），并且在室温下具有0.001–0.005的量子产率发射。一种配合物[Ru（4CAP-PTSC）（CO）（AsPh 3）2 ]（4）的晶体结构已通过单晶X射线晶体学解析，它表明这些配合物中存在扭曲的八面体几何形状。所有的配合物都表现出准可逆的一次电子还原（Ru II / Ru I）的范围在-0
• In silico and in vitro Antibacterial Assessment of Newly Synthesized Ni(II) Complexes of Thiosemicarbazone
  作者：Sudhansu Sekhar Swain、Monalisa Mahapatra、Sazad Ali、B.V.V. Ravi Kumar、Sudhir Kumar Paidesetty

  DOI：10.14233/ajchem.2022.23884

  日期：——

  Nowadays, most anti-infective agents or antibiotics are becoming resistant to several uropathogenic microorganisms. Thus, there is an urgent need of new potent candidates for treating infectious diseases and overcome the antibiotic resistance. Nickel(II) complexes of composition [Ni(Lig2)·2H2O]X2 have been synthesized with the ligand substituted benzaldehyde thiosemicarbazone (X = Cl). These obtained products were structurally interpreted by several spectroscopic studies includes FTIR for functional group detection, 1H & 13C NMR for the structural number of environment protons and carbons frame. The proposed Ni2+ complexes are octahedral structure and all ligands are coordinated with thiols or thiones and behaves as a bidentate manner. All the nickel(II) complexes were further screened in vitro antibacterial action against E. coli and S. aureus. The antibacterial activity of all the tested compounds, Ni(II) complex bearing 4-nitrobenzylidene thiosemicarbazone (4e) had shown significant inhibition against E. coli whereas overall assessment of antibacterial action indicates that all the compounds have been exhibited moderate to good inhibition growth bacterial with E. coli. Moreover, the binding affinity of the ligands had also been predicted through the molecular docking and physico-chemical properties were calculated. The synthesized nickel complexes could be more potent bacterial target inhibitor.

  如今，大多数抗感染药或抗生素对几种尿路病原微生物产生了抗药性。 微生物产生耐药性。因此，迫切需要新的强效候选药物来治疗感染性疾病和克服抗生素耐药性。 并克服抗生素耐药性。组成为 [Ni(Lig2)-2H2O]X2的镍(II)复合物 合成了配体取代苯甲醛硫代氨基甲酮（X = Cl）的镍（II）复合物。这些 产品的结构进行了解释。 傅立叶变换红外光谱（用于检测官能团）、1H & 和 13C NMR（用于检测环境质子和碳框架的结构数）。 所提出的 Ni2+ 复合物为八面体结构，所有配体都与硫醇或硫代 所有配体都与硫醇或硫醚配位，并表现为双齿方式。对所有镍（II）配合物进行了进一步的体外筛选 大肠杆菌和金黄色葡萄球菌的抗菌作用。所有测试化合物的抗菌活性都很好、 含 4-硝基亚苄基硫代氨基甲酮的 Ni（II）复合物（4e）对大肠杆菌有明显的抑制作用，而含 4-硝基亚苄基硫代氨基甲酮的 Ni（II）复合物（4f）对金黄色葡萄球菌有明显的抑制作用。 对大肠杆菌有明显的抑制作用，而抗菌作用的总体评估表明，所有化合物 都对大肠杆菌的细菌生长有中等到良好的抑制作用。此外，配体的结合 此外，还通过分子对接预测了配体的结合力，并计算了其物理化学性质。 计算。合成的镍配合物可能是更有效的细菌靶标 抑制剂。
• 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：——