(E)-N-phenyl-2-(thiophen-2-ylmethylene)hydrazine-1-carbothioamide | 199187-74-1

• 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: (E)-N-phenyl-2-(thiophen-2-ylmethylene)hydrazine-1-carbothioamide
• 英文别名: 2-thiophenecarbaldehyde N-phenylthiosemicarbazone；1-phenyl-3-[(E)-thiophen-2-ylmethylideneamino]thiourea
• CAS: 199187-74-1
• 化学式: C₁₂H₁₁N₃S₂
• 分子量: 261.371
• InChiKey: GFHBQBMHIDHBNM-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-phenyl-2-(thiophen-2-ylmethylene)hydrazine-1-carbothioamide 、 二苯基环丙烯酮 在 溶剂黄146 作用下， 以60%的产率得到(6,7-diphenyl-5-thiophen-2'-yl-pyrrolo[2,1-b]oxadiazolyl)-2-phenylamine
  参考文献：
  名称：

  环丙烯酮化学：合成新的吡咯并[2,1- b ] -1,3,4-恶二唑

  摘要：

  2,3-二苯基环丙烯酮（1）与亚烷基-N-苯基肼-碳硫酰胺2a - e反应形成吡咯并[2,1- b ] -1,3,4-恶二唑5a - e。

  DOI：

  10.1016/j.tetlet.2008.04.066
• 作为产物：
  描述：

  硫代异氰酸苯酯 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (E)-N-phenyl-2-(thiophen-2-ylmethylene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents

  摘要：

  In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 mu M, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial-mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112349

文献信息

• Optimization of Antitrypanosomatid Agents: Identification of Nonmutagenic Drug Candidates with in Vivo Activity
  作者：Guzmán Álvarez、Javier Varela、Pablo Márquez、Martín Gabay、Carmen Elena Arias Rivas、Karina Cuchilla、Gustavo A. Echeverría、Oscar E. Piro、Marlus Chorilli、Sandra M. Leal、Patricia Escobar、Elva Serna、Susana Torres、Gloria Yaluff、Ninfa I. Vera de Bilbao、Mercedes González、Hugo Cerecetto

  DOI：10.1021/jm500018m

  日期：2014.5.22

  selectivity and also performed mutagenicity studies. Proof of concept, in vivo studies, was conducted with two of the most promising derivatives (77 and 80). They were identified as candidates because they have (i) very simple and cost-effective syntheses; (ii) activity against different stages and strains of the parasite showing excellent in vivo behavior during the acute phase of Chagas disease; and

  由克鲁斯锥虫寄生虫引起的恰加斯病已在数千年前被描述过。目前，它影响到数以百万计的人，其中大多数在拉丁美洲，并且没有合适的药物来治疗它。为了找到合适的药物来解决这个问题，我们在这里报告了82种新化合物的设计，合成和表征。体外锥虫杀灭行为显示出超过20种具有抗克氏锥虫活性的杰出衍生物。此外，我们研究了对哺乳动物细胞的非特异性毒性，从而确定了它们的选择性，并进行了致突变性研究。使用两种最有希望的衍生物（77和80进行了体内研究的概念验证））。之所以将它们确定为候选者，是因为它们具有（i）非常简单且具有成本效益的综合方法；（ii）在恰加斯病急性期期间，针对不同阶段和种类的寄生虫的活性表现出优异的体内行为；（iii）非特异性毒性或诱变活性。
• Design, synthesis and characterization of novel Ni(II) and Cu(II) complexes as antivirus drug candidates against SARS-CoV-2 and HIV virus
  作者：  Aprajita、Mukesh Choudhary

  DOI：10.1016/j.molstruc.2022.133114

  日期：2022.9

  describes the structure-based design, synthesis and anti-virus effect of two new coordination complexes, a Ni(II) complex [Ni(L)2] (1) and a Cu(II) complex [Cu(L)2] (2) of (E)-N-phenyl-2-(thiophen-2-ylmethylene) hydrazine-1-carbothioamide(HL). The synthesized ligand was coordinated to metal ions through the bidentate-N, S donor atoms. The newly synthesized complexes were characterized by various spectroscopic

  本文介绍了两种新型配位配合物Ni(II)配合物[Ni(L) 2 ] ( 1 )和Cu(II)配合物[Cu(L) 2 ]的基于结构的设计、合成和抗病毒效果。] ( 2 ) (E)-N-苯基-2-(噻吩-2-基亚甲基)肼-1-硫代甲酰胺( HL )。合成的配体通过双齿N、S供体原子与金属离子配位。通过各种光谱和物理化学方法、粉末 XRD 分析以及 X 射线晶体学研究对新合成的配合物进行了表征。Ni(II) 配合物 [Ni(L) 2 ]( 1 ) 在正交晶系中结晶，空间群为Pbca，晶胞中有四个分子 (a = 9.857(3) Å, b = 7.749(2) Å, c = 32.292(10) Å, α = 90°, β = 90°, γ = 90°, Z= 4) 并揭示了扭曲的方形平面几何形状。在 Ni(II) 络合物 [Ni(L) 2 ] ( 1 )的晶体结构中探索了赫什菲尔德曲面和二维指纹
• Synthesis of thiophene-thiosemicarbazone derivatives and evaluation of their in vitro and in vivo antitumor activities
  作者：Jamerson Ferreira de Oliveira、Anekécia Lauro da Silva、Débora Barbosa Vendramini-Costa、Cezar Augusto da Cruz Amorim、Júlia Furtado Campos、Amélia Galdino Ribeiro、Ricardo Olímpio de Moura、Jorge Luiz Neves、Ana Lúcia Tasca Gois Ruiz、João Ernesto de Carvalho、Maria do Carmo Alves de Lima

  DOI：10.1016/j.ejmech.2015.09.036

  日期：2015.11

  A series of thiophene-2-thiosemicarbazones derivatives (5-14) was synthesized, characterized and evaluated for their antitumor activity. They were tested in vitro against human tumor cell lines through the colorimetric method. The results revealed that compounds 7 and 9 were the most effective in inhibiting 50% of the cell growth after 48 h of treatment. As compound 7 showed a potent anti-proliferative profile, it has been chosen for further studies in 786-0 cell line by flow cytometry. Treatments with compound 7 (50 mu M) induced early phosphatidylserine exposure after 18 h of exposure and this process progressed phosphatidylserine exposure with loss of cell membrane integrity after 24 h of treatment, suggesting a time-dependent cell death process. Regarding the cell cycle profile, no changes were observed after treatment with compound 7 (25 mu m), suggesting a mechanism of cell death independent on the cell cycle. The in vivo studies show that compound 7 possess low acute toxicity, being the doses of 30-300 mgK(-1) chosen for studies in Ehrlich solid tumor model in mice. All doses were able to inhibit tumor development being the lowest one the most effective. Our findings highlight thiophene-2-thiosemicarbazones as a promising class of compounds for further studies concerning new anticancer therapies. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents
  作者：Xin-Hui Zhang、Bo-Wang、Yuan-Yuan Tao、Qin Ma、Hao-Jie Wang、Zhang-Xu He、Hui-Pan Wu、Yi-Han Li、Bing Zhao、Li-Ying Ma、Hong-Min Liu

  DOI：10.1016/j.ejmech.2020.112349

  日期：2020.8

  In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 mu M, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial-mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer. (C) 2020 Elsevier Masson SAS. All rights reserved.
• Chemistry of cyclopropenones: synthesis of new pyrrolo[2,1-b]-1,3,4-oxadiazoles
  作者：Ashraf A. Aly、Alaa A. Hassan、Mohamed A. Ameen、Alan B. Brown

  DOI：10.1016/j.tetlet.2008.04.066

  日期：2008.6

  2,3-Diphenylcyclopropenone (1) reacts with ylidene-N-phenylhydrazine-carbothioamides 2a–e to form the pyrrolo[2,1-b]-1,3,4-oxadiazoles 5a–e.

  2,3-二苯基环丙烯酮（1）与亚烷基-N-苯基肼-碳硫酰胺2a - e反应形成吡咯并[2,1- b ] -1,3,4-恶二唑5a - e。