4-diethylaminosalicylaldehyde thiosemicarbazone | 316136-61-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-diethylaminosalicylaldehyde thiosemicarbazone
• 英文别名: 4(N,N')-diethylaminosalicylaldehydethiosemicarbazone；4(N,N)-diethylaminosalicylaldehyde-4-(N)-thiosemicarbazone；2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazine-1-carbothioamide；2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazinecarbothioamide；[[4-(Diethylamino)-2-hydroxyphenyl]methylideneamino]thiourea
• CAS: 316136-61-5
• 化学式: C₁₂H₁₈N₄OS
• 分子量: 266.367
• InChiKey: ZUOLKXPUIOKBRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 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：
  106
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(triphenylphosphine)nickel(II) chloride 、 4-diethylaminosalicylaldehyde thiosemicarbazone 以 乙醇 、 二氯甲烷 为溶剂， 以69%的产率得到[Ni(II)(triphenylphosphine)(OC6H3(NEt2)CHNNC(NH2)S)]
  参考文献：
  名称：

  Nickel(II) complexes containing thiosemicarbazone and triphenylphosphine: Synthesis, spectroscopy, crystallography and catalytic activity

  摘要：

  Four new Ni(II) complexes of the general formula [Ni(PPh3)(L)](L = dibasic tridentate ligand derived from 4-diethylamino-salicylaldehyde and thiosemicarbazide or 4-N-substituted thiosemicarbazide) have been reported. The new complexes have been synthesized and characterized by analytical and spectroscopic (IR, electronic, H-1 NMR and P-31 NMR) techniques. Molecular structure of one of the complexes has been determined by X-ray crystallography. The complex. [Ni(PPh3)(L4)] (H(2)L4 = thiosemicarbazone prepared from 4-diethylamino-salicylaldehyde and 4-phenylthiosemicarbazide) crystallized in monoclinic space group with two molecules per unit cell and has the dimensions of a = 13.232(6) angstrom, b= 10.181(5) angstrom, c = 13.574(7) angstrom, alpha = 90 degrees, beta = 98.483(2)degrees and gamma =90 degrees. Catalytic activity of the complexes has been explored for aryl-aryl coupling reaction. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.06.046
• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 、 氨基硫脲 在 溶剂黄146 作用下， 以69%的产率得到4-diethylaminosalicylaldehyde thiosemicarbazone
  参考文献：
  名称：

  强效硫半脲酮类化合物作为酪氨酸酶抑制剂的合成，筛选和生物学活性

  摘要：

  酪氨酸酶在黑色素生成中起重要作用。酪氨酸酶抑制不仅可能是减轻皮肤色素沉着的一种手段，而且是水果和蔬菜保存的最有效方法。硫代氨基脲类化合物因其具有抗肿瘤，抗菌和抗疟的特性而具有潜在的治疗活性，因此受到了极大的关注。在这项研究中，我们集中于作为新型酪氨酸酶抑制剂的强效硫代半脲类化合物的筛选，毒性，相互作用和抑制活性。结果表明，由于不存在邻位基团，抑制剂的效力大大降低。-羟基和通过改变苯甲醛的取代基得到改善。为了建立药效基团模型，我们探索了在酪氨酸酶活性位点上的硫半脲类化合物的结合模式。使用AUTODOCK程序进行了对接分析，以解释与酪氨酸酶活性位点结合的柔性硫代半碳胺分子，因为它们在大小和疏水性上都与酪氨酸酶的活性位点和底物通道完美匹配。它们的结合主要通过抑制剂中硫和氮原子与酪氨酸酶活性位点中的双核铜的配位作用。仍然需要对这些类型的抑制剂进行进一步的补充研究，例如用于治疗异常黑色素色素沉着和抑制食物或水果褐变的潜在候选药物。

  DOI：

  10.1039/c9nj02360g

文献信息

• Caenorhabditis elegans as a model for exploring the efficacy of synthesized organoruthenium complexes for aging and Alzheimer's disease a neurodegenerative disorder: A systematic approach
  作者：G. Devagi、G. Shanmugam、A. Mohankumar、P. Sundararaj、F. Dallemer、P. Kalaivani、R. Prabhakaran

  DOI：10.1016/j.jorganchem.2017.03.023

  日期：2017.6

  article deals with the preparation and characterisation of new organoruthenium(II) complexes, namely [RuCp(Dea-Sal-tsc)(PPh3)] (1), [RuCp(Dea-Sal-mtsc)(PPh3)] (2), [RuCp(Dea-Sal-etsc)(PPh3)] (3) and [RuCp(Dea-Sal-ptsc)(PPh3)] (4). The new ruthenium(II) complexes were characterized by various analytical, spectral techniques. The structure of the ligand [H2-Dea-Sal-tsc] and the complex [RuCp(Dea-Sal-tsc)(PPh3)]

  本文讨论了新型有机钌（II）配合物的制备和表征，即[RuCp（Dea-Sal-tsc）（PPh 3）]（1），[RuCp（Dea-Sal-mtsc）（PPh 3）] （2），[RuCp（Dea-Sal-etsc）（PPh 3）]（3）和[RuCp（Dea-Sal-ptsc）（PPh 3）]（4）。新的钌（II）配合物通过各种分析，光谱技术表征。通过X射线晶体学证实了配体[H 2 -Dea-Sal-tsc]和配合物[RuCp（Dea-Sal-tsc）（PPh 3）]（1）的结构。配合物（1-4）以秀丽隐杆线虫为模型研究毒性，抗逆性，衰老和神经保护作用。通过DPPH自由基清除测定法进行体外清除自由基的活性，复合物（1-4）的清除活性高于标准维生素C（IC 50  = 5.28±0.10）。用复合物4处理过的mev-1突变蠕虫的寿命增加了22.4％以上。复4触发的DAF-16的核定位，提高SOD
• Effect directed synthesis of a new tyrosinase inhibitor with anti-browning activity
  作者：Ignacio Cabezudo、I. Ayelen Ramallo、Victoria L. Alonso、Ricardo L.E. Furlan

  DOI：10.1016/j.foodchem.2020.128232

  日期：2021.3

  TLC bioautography, (c) inhibitor identification via mass spectrometry coupled to bioautography. During these proof-of-concept experiments, the approach led to the straightforward identification of a new thiosemicarbazone with improved tyrosinase inhibition properties and fresh-cut apple slices antibrowning effect when compared to kojic acid. In conclusion, the platform represents an interesting strategy

  抑制酶促褐变是提高食品质量的有吸引力的目标。这项工作的目的是基于（a）一锅制备硫代氨基脲化合物文库，（b）使用酪氨酸酶TLC生物自显影技术进行生物学评估，（c）通过抑制剂鉴定来鉴定酪氨酸酶抑制剂的新平台。质谱结合生物自显影。在这些概念验证实验过程中，该方法可直接鉴定出一种新的硫代半碳环素，与硫辛酸相比，该硫代半碳硫酮具有增强的酪氨酸酶抑制特性和鲜切的苹果片抗褐变作用。总之，该平台代表了发现此类抑制剂的有趣策略。
• Binuclear Ni(II) complexes containing ONS donor Schiff base ligands: Preparation, spectral characterization, X-ray crystallography and biological exploration
  作者：G. Kalaiarasi、S. Dharani、S. Rex Jeya Rajkumar、Vincent M. Lynch、R. Prabhakaran

  DOI：10.1016/j.jinorgbio.2020.111176

  日期：2020.10

  molecular structure of complexes [Ni2(H-DEAsal-tsc)2(μ-dppm)]·2Cl (1) and [Ni2(DEAsal-ptsc)2(μ-dppm)] (4) have been confirmed by single crystal X-ray diffraction studies. The analysis indicated that in complex 1, the ligand [H2-DEAsal-tsc] coordinated as monobasic tridentate donor through phenolic oxygen, azomethine nitrogen and thione sulfur atoms. However, in complex 4, the ligand [H2-DEAsal-ptsc] behaved

  四个双核Ni（II）络合物[ [Ni 2（H-DEAsal-TSC）2（μ-dppm）]·2Cl（1），[Ni 2（DEAsal-mTSC）2（μ-dppm）]（2），从配体即4（N，N）合成[Ni 2（DEAsal-eTSC）2（μ-dppm）]（3）和[Ni 2（DEAsal-pTSC）2（μ-dppm）]（4）。 -diethylaminosalicylaldehyde-4（ñ）-thiosemicarbazone [ ħ 2 - DEAsal-TSC ] ħ 2大号1 /4（ñ，Ñ）-diethylaminosalicylaldehyde-4（Ñ） -甲基缩氨基硫脲[ ħ 2 - DEAsal-MTSC ] ħ 2大号2 /4（Ñ，Ñ）-diethylaminosalicylaldehyde-4（Ñ） -乙基缩氨基硫脲[ ħ 2 - DEAsal-ETSC ] ħ 2 L 3/4（
• New palladium metallacycles containing 4(N,N′)-diethylaminosalicylaldehyde-4(N)-thiosemicarbazones: Synthesis, spectral, structural and DNA/protein binding studies
  作者：P. Kalaivani、C. Umadevi、R. Prabhakaran、F. Dallemer、P.S. Mohan

  DOI：10.1016/j.ica.2015.08.031

  日期：2015.11

  absorption and emission titration methods. Based on the observations, an intercalative binding mode of DNA has been proposed. The protein binding abilities of the new complexes along with their precursor were monitored by quenching of tryptophan and tyrosine residues using BSA as model protein. From the studies, it was found that the new palladium metallacycles exhibited better affinity than their

  摘要在与[PdCL2（AsPh3）2] 1：1化学计量反应中，研究了4（N，N'）-二乙基氨基水杨醛-4（N）取代的硫代半氨基甲酮（H2L1-4）的通用配位行为。所有新的配合物（1-4）均通过分析，红外，吸收和1H NMR光谱学表征。配合物[Pd（DeaSal-tsc）（AsPh3）]（1），[Pd（H-DeaSal-mtsc）（AsPh3）]（2）和[Pd（H-DeaSal-etsc）（AsPh3）]（3）通过单晶X射线衍射研究对它们的结构进行了表征。晶体学结果表明，配体H2L1通过形成六个和五个成员环而配位为配合物1中的单负三齿ONS供体配体。鉴于配体H2L2和H2L3通过留下第三个潜在的供体原子而形成五元螯合环，从而在2和3中作为单负性双齿NS供体与钯结合，酚氧保持完整，不参与键合。酚氧的不参与可能是由于酚氢和N 2氮之间的分子内氢键。钯（II）前体[PdCL2（AsPh3）2]，配体（H2L1
• Semicarbazone and thiosemicarbazone appended 4-diethylamino-2‑hydroxybenzyl compounds as highly selective bifunctional chemosensors: An experimental and computational approach
  作者：Sethu Amuthakala、Sundaram Bharathi、Aziz Kalilur Rahiman

  DOI：10.1016/j.ica.2022.121302

  日期：2023.2

  and F− anion in a mixture of solvent, CH3CN:CH3OH (8:2, v/v). The receptor S3 possesses high sensitivity and selectivity in comparison with the receptors S1 and S2. The binding constant and limit of detection of the receptors with sensed cations and anion showed high sensitivity and selectivity towards Co2+ cation with order of magnitude 6, greater than the other sensed cations. In addition, the receptors

  三种双功能化学传感器，2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazinecarboxamide (S1), 2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazinecarbothioamide (S2) and 2-(4-(diethylamino)-2 -hydroxybenzylidene) -N - methylhydrazinecarbothioamide (S3) 已被设计和合成用于在室温下识别溶液中的无机阳离子和阴离子。受体S2的结构通过单晶X射线衍射技术证实，其在单斜晶系P2 1/n空间群中结晶。阳离子（Mn 2+、Fe 2+、Co 2+、Ni 2+、Cu 2+、Zn 2+和Pb 2+ ）的选择性和灵敏度) 和阴离子（F -、Cl -、Br -、I -、HSO 4 -和 H 2 PO