ethyl thiosemicarbazide | 21149-56-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl thiosemicarbazide
• 英文别名: N-ethyl thiosemicarbazide；1-ethyl-thiosemicarbazide；(Ethylamino)thiourea；ethylaminothiourea
• CAS: 21149-56-4
• 化学式: C₃H₉N₃S
• mdl: MFCD19204293
• 分子量: 119.191
• InChiKey: IDAYARXLWPWWNI-UHFFFAOYSA-N

物化性质

• 沸点：
  187.4±23.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl thiosemicarbazide 、 5-硝基水杨醛 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以82%的产率得到5-nitro-salicylaldehyde-N¹-ethyl-thiosemicarbazone
  参考文献：
  名称：

  Synthesis, structures and antimicrobial activity of 5-nitro-salicylaldehyde-thiosemicarbazonates of zinc(II) coordinated to substituted bipyridines/phenanthrolines

  摘要：

  Reactions of zinc(II) with 5-nitro-salicylaldehyde-N-1 -substituted thiosemicarbazones {(5-NO2-2-HO-C6H4)C-2(H)=N-3-(NH)-H-2-C-1(=S)-(NHR)-H-1; R = H, H2L1; Me, H2L2; Et, H2L3; Ph, H2L4 ) and 4,4'-dimethyl-2,2'-bipyridine (dm-bipy), 2,9-dimethyl-1,10-phenanthroline (dm-phen) and 3,4,7,8-tetramethyl-1, 10-phenanthroline (tm-phen) as co-ligands, have yielded complexes of stoichiometry, [Zn(L-n)(L)] {n = 1-4; L = dm-bipy, 1, 4, 7, 10; dm-phen, 2, 5, 8, 11; tm-phen, 3, 6, 9, 12) characterized by elemental analysis, infrared and electronic absorption spectroscopy and single crystal X-ray crystallography. Complexes 9 and 10 have distorted trigonal bipyramidal geometry (tau = 0.529-0.580), while complexes 5, 8 and 11 have distorted square pyramidal geometry (tau = 0.004-0.250). They displayed fluorescence bands at lambda(max) - 430-440 nm. In comparison to unsubstituted bipyridines/phenanthrolines, these zinc(II) complexes have shown higher antimicrobial activity with low minimum inhibitory concentration (MIC) against the clinical isolate methicillin resistant Staphylococcus aureus (MRSA), Gram positive bacteria, namely, Staphylococcus aureus (MTCC740), Enterococcus faecalis (MTCC439), Gram negative bacteria, namely, Klebsiella pneumonia 1 (MTCC109), Escherichia coli (MTCC119), Salmonella typhimurium 1 (MTCC98) and one yeast strain Candida albicans (MTCC227). These complexes tested were found to be cytotoxic to microorganisms (bactericidal/fungicidal). (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.03.027
• 作为产物：
  描述：

  (1E)-3-氨基-1-亚乙基硫脲 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 ethyl thiosemicarbazide
  参考文献：
  名称：

  Jensen,K.A. et al., Acta Chemica Scandinavica (1947), 1968, vol. 22, p. 1 - 50

  摘要：

  DOI：

文献信息

• Copper(<scp>ii</scp>) complexes of hybrid hydroxyquinoline-thiosemicarbazone ligands: GSK3β inhibition due to intracellular delivery of copper
  作者：James L. Hickey、Peter J. Crouch、Sithorn Mey、Aphrodite Caragounis、Jonathan M White、Anthony R. White、Paul S. Donnelly

  DOI：10.1039/c0dt01176b

  日期：——

  Cognitive decline associated with Alzheimer's disease appears to be related to the hyper-phosphorylation of the protein tau as a consequence of increased activity of glycogen synthase kinase 3β (GSK3β), and subsequent formation of neurotoxic neurofibrillary tangles. Abberant metal ion homeostasis, particularly involving copper has been implicitly linked to the pathogenesis of the disease. Increasing intracellular copper concentrations has been found to trigger pathways that result in inhibition of GSK3β. The syntheses and characterisation of tetradentate hybrid hydroxyquinoline-thiosemicarbazone proligands is presented. The ligands form stable complexes with CuII where the copper ion is four coordinate and essentially square planar as characterised by single crystal X-ray crystallography. The reduction of the metal ion to CuI has been studied by electrochemical techniques and occurs at potentials that permit intracellular reduction. The new complexes show class dependent cell membrane permeability in neuronal-like SH-SY5Y cells with subsequent increases in intracellular copper concentrations. The increased intracellular copper results in a dose-dependent inhibition (phosphorylation) of GSK3β.

  与阿尔茨海默病相关的认知衰退似乎与糖原合酶激酶3β（GSK3β）活性增强导致蛋白tau的高度磷酸化，从而形成神经毒性神经原纤维缠结有关。异常的金属离子稳态，特别是涉及铜的部分，已隐含地与该疾病的病理机制相关联。发现增加细胞内铜浓度会触发导致GSK3β抑制的途径。本文介绍了四齿杂化羟基喹啉-缩硫半卡巴脘前配体的合成与表征。这些配体能与CuII形成稳定的配合物，其中铜离子为四配位且基本呈平面正方形，这一特点通过单晶X射线晶体学进行了表征。通过电化学技术研究了金属离子的还原为CuI的过程，并且发生在允许细胞内还原的电位。这些新的配合物在类神经细胞SH-SY5Y中表现出依赖类型的细胞膜透过性，随后增加了细胞内铜浓度。增加的细胞内铜导致了剂量依赖性的GSK3β抑制（磷酸化）。
• 3-Thiovinyl-cephalosporins
  申请人：Rhone-Poulenc Industries

  公开号：US04307116A1

  公开（公告）日：1981-12-22

  Novel cephalosporins of the general formula (I); ##STR1## in which R is alkyl, L-2-amino-2-carboxy-ethyl, phenyl, pyridyl, pyridyl-N-oxide, pyrimidin-2-yl, substituted pyridazin-3-yl, 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 4-position, 1,3,4-triazol-5-yl or 2-alkoxycarbonyl-1,3,4-triazol-5-yl substituted in the 1-position, 1,4-dialkyl-5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl, 1-alkyl-5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl, 2-alkyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl, triazol-5-yl, 1,3,4-thiadiazol-5-yl which is substituted or unsubstituted, 1,2,4-thiadiazol-5-yl which is substituted, 1,3,4-oxadiazol-5-yl which is substituted or unsubstituted, oxazol-2-yl which is substituted or unsubstituted or tetrazol-5-yl which is substituted or unsubstituted in the 1-position, R' is a hydrogen atom or a radical of the general formula (II); ##STR2## and R.sup.o is hydrogen, alkyl, vinyl or cyanomethyl, as well as their salts, are useful as anti-bacterial agents.

  新型头孢菌素类化合物，其通式为(I)；##STR1##其中R为烷基、L-2-氨基-2-羧基乙基、苯基、吡啶基、吡啶基-N-氧化物、嘧啶-2-基、取代的吡啶-3-基、4-位取代的5,6-二氧代-1,4,5,6-四氢-1,2,4-三嗪-3-基、1,3,4-三唑-5-基或1-位取代的2-烷氧羰基-1,3,4-三唑-5-基、1,4-二烷基-5,6-二氧代-1,4,5,6-四氢-1,2,4-三嗪-3-基、1-烷基-5,6-二氧代-1,4,5,6-四氢-1,2,4-三嗪-3-基、2-烷基-5,6-二氧代-1,2,5,6-四氢-1,2,4-三嗪-3-基、三唑-5-基、取代或未取代的1,3,4-噻二唑-5-基、取代的1,2,4-噻二唑-5-基、取代或未取代的1,3,4-噁二唑-5-基、取代或未取代的噁唑-2-基或1-位取代或未取代的四唑-5-基，R'为氢原子或通式(II)的基团；##STR2##且R.sup.o为氢、烷基、乙烯基或氰甲基，以及它们的盐，可用作抗菌剂。
• Influence of terminal substitution on structural, DNA, Protein binding, anticancer and antibacterial activities of palladium(ii) complexes containing 3-methoxy salicylaldehyde-4(N) substituted thiosemicarbazones
  作者：P. Kalaivani、R. Prabhakaran、E. Ramachandran、F. Dallemer、G. Paramaguru、R. Renganathan、P. Poornima、V. Vijaya Padma、K. Natarajan

  DOI：10.1039/c1dt11838b

  日期：——

  of the complexes with calf-thymus DNA (CT-DNA) has been explored by absorption and emission titration methods. Based on the observations, an electrostatic binding mode of DNA has been proposed. The protein binding studies were monitored by quenching of tryptophan and tyrosine residues in the presence of complexes using Lysozyme as model protein. Antibacterial activity studies of the complexes have been

  在与[PdCl 2（PPh 3）2 ]的等摩尔反应中，观察到3-甲氧基水杨醛-4（N）-取代的硫代半氨基甲酮的可变螯合行为。通过各种分析，光谱技术（质量，1 H-NMR，吸收，IR）对新配合物进行了表征。所有新的配合物都通过单晶X射线衍射进行结构表征。晶体学结果表明，配位体ħ 2大号1和H 2大号4被协调作为络合物binegative三齿ONS供体配体1和4通过形成6个五元环。但是，配体H 2通过形成五元螯合环，L 2和H 2 L 3以单负性二齿NS供体的形式在2和3中与钯结合。从该研究中发现，在末端4（N）-氮上的取代可能对硫代半脲的螯合能力有影响。2和3中存在氢键可能负责防止酚氧与金属离子的配位。络合物与小牛胸腺DNA（CT-DNA）的相互作用已通过吸收和发射滴定法进行了研究。基于这些观察，已经提出了DNA的静电结合模式。蛋白质结合研究通过淬灭色氨酸溶菌酶作为模型蛋白，在复合物存在下，
• Thiosemicarbazone platinacycles with tertiary phosphines. Preparation of novel heterodinuclear platinum–tungsten complexes
  作者：Darío Lata、M. Teresa Pereira、Juan M. Ortigueira、Javier Martínez、Brais Bermúdez、Jesús J. Fernández、José M. Vila

  DOI：10.1016/j.poly.2012.04.015

  日期：2012.6

  afforded the tetranuclear platinum(II) compounds [Pt(R1C6H3)C(H) NN C(S)NHR2}]4 (1a–1f) with the ligand as terdentate [C,N,S] after C–H activation and NH deprotonation. The reaction of 1a–1f with PPh3 in 1:4 M ratio gave the mononuclear compounds [Pt(R1C6H3)C(H) NN C(S)NHR2}(PPh3)] (2a–2f). Treatment of 1a–1f with large-bite diphosphines Ph2P(CH2)nPPh2 (n = 2, dppe; n = 3, dppp; n = 4, dppb) afforded the

  硫代半咔唑（R1C6H4）C（H）NN（H）C（S）NHR2的抽象处理[R1，R2：4-Me，H（a）; 4-Me，Me（b）; 4-Me，Et（c）; 2-Me，H（d）; 2-Me，Me（e）; 2-Me，Et（f）]与顺式[PtMe2（cod）]提供四核铂（II）化合物[Pt （（R1C6H3）C（H）NN C（S）NHR2}] 4（1a-1f） C–H活化和NH去质子化后，配体为齿状[C，N，S]。1a-1f与PPh3以1：4 M的比例反应生成单核化合物[Pt （（R1C6H3）C（H）NN C（S）NHR2}（PPh3）]（2a-2f）。用大剂量二膦Ph2P（CH2）nPPh2（n = 2，dppe; n = 3，dppp; n = 4，dppb）处理1a-1f得到双核化合物[Pt [（R1C6H3）C（H）N –N = C（S）NHR2]} 2 μ-Ph2P（CH2）n
• [EN] COPPER COMPLEXES FOR TREATMENT OF NEURODEGENERATIVE DISORDERS<br/>[FR] COMPLEXES DE CUIVRE DESTINÉS AU TRAITEMENT D'ÉTATS NEURODÉGÉNÉRATIFS
  申请人：ALS THERAPY DEVELOPMENT INST

  公开号：WO2022047014A1

  公开（公告）日：2022-03-03

  The present disclosure relates to copper complexes, pharmaceutical compositions comprising these complexes, chemical processes for preparing these complexes, and their use in the treatment of neurodegenerative disease, e.g., amyotrophic lateral sclerosis (ALS).

  本公开涉及铜配合物、包含这些配合物的药物组合物、制备这些配合物的化学过程，以及它们在治疗神经退行性疾病（例如肌萎缩侧索硬化症）中的应用。