(2E)-2-[4-(diethylamino)benzylidene]hydrazinecarbothioamide | 1598434-88-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2E)-2-[4-(diethylamino)benzylidene]hydrazinecarbothioamide
• 英文别名: [(E)-[4-(diethylamino)phenyl]methylideneamino]thiourea
• CAS: 1598434-88-8
• 化学式: C₁₂H₁₈N₄S
• 分子量: 250.368
• InChiKey: BACMXYJKOOIPTI-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-2-[4-(diethylamino)benzylidene]hydrazinecarbothioamide 在 碳酸氢钠 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 [Ni((2E)-2-[4-(diethylamino)benzylidene]-N-[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydrazinecarbothioamide)₂]
  参考文献：
  名称：

  Synthesis, characterization, and in vitro anti-neoplastic activity of novel vic-dioximes bearing thiosemicarbazone side groups and their mononuclear complexes

  摘要：

  Two novel vicinal dioxime ligands containing thiosemicarbazone units, (2E)-2-[4-(diethylamino)benzylidene]-N-[(1Z, 2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydrazine carbothioamide ((LH2)-H-1) and (2E)-2-[4-(dimethylamino)benzylidene]-N-[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydra-zinecarbothioamide ((LH2)-H-2), were synthesized. Using the HL-60 human leukemia cell line, the in vitro anti-neoplastic activity of these thiosemicarbazone-oxime derivatives was evaluated. Mononuclear nickel(II), copper(II), and cobalt(II) complexes with a metal: ligand ratio of 1:2 for both the (LH2)-H-1 and (LH2)-H-2 ligands were also synthesized. To characterize these compounds, Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS), magnetic susceptibility measurements, H-1 and C-13 nuclear magnetic resonance (NMR), ultraviolet-visible (UV-Vis) absorption spectroscopy, heteronuclear multiple-bond correlation (HMQC), and elemental analysis were performed. For (LH2)-H-1, (LH2)-H-2, and each of their derivatives, antiproliferative effects against HL-60 cells were exhibited and the associated IpC50 values ranged from 5 mu M to 20 mu M. Furthermore, (LH2)-H-1 and its derivatives inhibited the proliferation of HL-60 cells more effectively than (LH2)-H-2, and 5 mu M [Cu((LH)-H-1)(2)] exhibited the strongest antiproliferative activity. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.01.003
• 作为产物：
  描述：

  氨基硫脲 、 N,N-二乙基-4-氨基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以83 %的产率得到(2E)-2-[4-(diethylamino)benzylidene]hydrazinecarbothioamide
  参考文献：
  名称：

  新型N-功能化噻唑烷酮的合成、表征、DFT、抗菌、ADME-T 特性和分子对接

  摘要：

  一系列新的N-功能化噻唑烷酮已通过三个步骤合成。物理化学和光谱技术，如熔点分析、IR、H 和 C NMR 已用于表征合成的化合物。借助密度泛函理论（DFT），对合成化合物优化的分子结构、红外光谱建模、反应性、稳定性和一些量子化学特性进行了建模。事实证明，实验结果与理论结果之间存在显着的一致性。此外，还评估了所研究化合物的抗菌活性，以便具体了解相关的作用机制。根据预计的 ADME-T 和药代动力学参数，它们还表现出良好的口服生物利用度。分子对接也被用来预测所研究的药物对 DNA 旋转酶 II 的抑制作用。

  DOI：

  10.1016/j.molstruc.2024.138004

文献信息

• VLADZIMIRSKA, O. V.;YAROSHCHUK, S. M., FARMATSEVTICHNIJ ZH., 1981, N 4, 37-39,
  作者：VLADZIMIRSKA, O. V.、YAROSHCHUK, S. M.

  DOI：——

  日期：——
• PRAKASH O.; TOMER R. K.; KODALI D. R., J. INDIAN CHEM. SOC., 1978, 55, NO 9, 919-921
  作者：PRAKASH O.、 TOMER R. K.、 KODALI D. R.

  DOI：——

  日期：——
• Synthesis, characterization, and in vitro anti-neoplastic activity of novel vic-dioximes bearing thiosemicarbazone side groups and their mononuclear complexes
  作者：İlknur Babahan、Ali Özmen、Nil Orhan、Didem Kazar、Esin Hafize Değirmenci

  DOI：10.1016/j.bioorg.2014.01.003

  日期：2014.4

  Two novel vicinal dioxime ligands containing thiosemicarbazone units, (2E)-2-[4-(diethylamino)benzylidene]-N-[(1Z, 2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydrazine carbothioamide ((LH2)-H-1) and (2E)-2-[4-(dimethylamino)benzylidene]-N-[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]hydra-zinecarbothioamide ((LH2)-H-2), were synthesized. Using the HL-60 human leukemia cell line, the in vitro anti-neoplastic activity of these thiosemicarbazone-oxime derivatives was evaluated. Mononuclear nickel(II), copper(II), and cobalt(II) complexes with a metal: ligand ratio of 1:2 for both the (LH2)-H-1 and (LH2)-H-2 ligands were also synthesized. To characterize these compounds, Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS), magnetic susceptibility measurements, H-1 and C-13 nuclear magnetic resonance (NMR), ultraviolet-visible (UV-Vis) absorption spectroscopy, heteronuclear multiple-bond correlation (HMQC), and elemental analysis were performed. For (LH2)-H-1, (LH2)-H-2, and each of their derivatives, antiproliferative effects against HL-60 cells were exhibited and the associated IpC50 values ranged from 5 mu M to 20 mu M. Furthermore, (LH2)-H-1 and its derivatives inhibited the proliferation of HL-60 cells more effectively than (LH2)-H-2, and 5 mu M [Cu((LH)-H-1)(2)] exhibited the strongest antiproliferative activity. (C) 2014 Elsevier Inc. All rights reserved.
• Synthesis, characterization, DFT, antibacterial, ADME-T properties, and molecular docking of new N-functionalized thiazolidinones
  作者：Rabah Boudissa、Abdelmadjid Benmohammed、Nadjib Chafai、Amel Boudechicha、Nawel Rekiba、Hafida Lagraa、Mahdi Achour、Omar Khoumeri、Ayada Djafri、Thierry Terme、Patrice Vanelle

  DOI：10.1016/j.molstruc.2024.138004

  日期：2024.7

  With the aid of density functional theory (DFT), the synthesized compounds optimized molecular structures, IR spectra modeling, reactivity, stability, and several quantum chemical characteristics were all modeled. It was demonstrated that there is significant agreement between the experimental and theoretical results. Furthermore, the antibacterial activity of the compounds under investigation was assessed

  一系列新的N-功能化噻唑烷酮已通过三个步骤合成。物理化学和光谱技术，如熔点分析、IR、H 和 C NMR 已用于表征合成的化合物。借助密度泛函理论（DFT），对合成化合物优化的分子结构、红外光谱建模、反应性、稳定性和一些量子化学特性进行了建模。事实证明，实验结果与理论结果之间存在显着的一致性。此外，还评估了所研究化合物的抗菌活性，以便具体了解相关的作用机制。根据预计的 ADME-T 和药代动力学参数，它们还表现出良好的口服生物利用度。分子对接也被用来预测所研究的药物对 DNA 旋转酶 II 的抑制作用。