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International Journal of Analytical Mass Spectrometry and Chromatography 2019年第2期7卷 19-34页

作者： Belén Gastaca Hernán Rubén Sánchez Fiorella Menestrina Maricel Caputo María de las Mercedes Schiavoni Jorge Javier Pedro Furlong Laboratory of Organic Compounds Studies (LADECOR) Department of Chemistry Facultad de Ciencias Exactas National University of La Plata La Plata Argentina Institute of Physics of Liquids and Biological Systems (IFLySIB CONICET) National University of La Plata La Plata Argentina Laboratory of Research and Development of Analytical Methods (LIDMA) Department of Chemistry Facultad de Ciencias Exactas National University of La Plata La Plata Argentina

Tautomeric forms of thiosemicarbazones have been investigated by spectrometric methods, their chemical reactivity and theoretical calculations of the relative tautomers stabilities. The mass spectral fragmentation of thiosemicarbazones synthesized from acetophenones has been studied by CG/MS. The analysis of the corresponding spectra shows not only the regular fragmentation mechanisms but homolytic ruptures from even-electron species. 1H NMR spectra exhibit signals for the most intense open thioketo tautomeric structure, although when using TFA a ring structure is observed in the corresponding tautomeric equilibrium. Density Functional Theory calculations (DFT) also provide evidence to support the experimental observations by GC-MS and 1H NMR. Methylation reactions give support to the occurrence of the thioenol tautomeric form which would be the second most abundant according to the Density Functional Theoretical calculations.

关键词： thiosemicarbazones Tautomerism MS NMR Theoretical Calculations

In vivo anticancer activity of vanillin,benzophenone and acetophenone thiosemicarbazones on Swiss albino mice

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Journal of Coastal Life Medicine 2014年第10期2卷 811-816页

作者： Sha Md.Shahan Shahriar Shaikh M Mohsin Ali Mele Jesmin Md.Khairul Islam Sarozit Mondal Department of Applied Chemistry and Chemical Engineering University of RajshahiRajshahi-6205Bangladesh

Objective:To study the anticancer activities of three schiff bases viz.vanillin thiosemicarbazone,benzophenone thiosemicarbazone and acetophenone thiosemicarbazone against Ehrlich ascites carcinoma(EAC)cells in Swiss albino mice.Methods:Synthesized compounds have administrated into the intraperitoneal cavity of the EAC inoculated mice at two doses.The anticancer activities have studied by monitoring the parameters such as cell growth inhibition,tumor weight measurement,survival time of EAC bearing mice as well as the changes in depleted hematological parameters due to tumorgenesis.All such data have been compared with those of a known standard drug bleomycin at the dose of 0.3 mg/kg(i.p.).Results:It has been found that these bases enhanced life span,reduced average tumor weight and inhibited tumor cell growth of EAC cell bearing mice remarkably.The results were similar in potency to those obtained with bleomycin.It was also found that the depleted hematological parameters(red blood count,white blood count and haemoglobin content)were found to be restored gradually towards normal within few weeks after ceasing the treatment.Conclusions:The compounds can be primarily considered more or less as potent anticancer agents.

关键词： Anticancer activity Ehrlich ascites carcinoma cells thiosemicarbazones

GC/MS Analyses of thiosemicarbazones Synthesized from Acetophenones: Thermal Decay and Mass Spectra Features

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International Journal of Analytical Mass Spectrometry and Chromatography 2015年第1期3卷 1-13页

作者： Belén Gastaca Gastón Galletti Hernán Rubén Sánchez Reinaldo Pis Diez María de las Mercedes Schiavoni Jorge Javier Pedro Furlong Laboratorio de Estudio de Compuestos Orgánicos (LADECOR) Departamento de Química Facultad de Ciencias Exactas Universidad Nacional de La Plata La Plata Argentina CEQUINOR Centro de Química Inorgánica (CONICET UNLP) Facultad de Ciencias Exactas UNLP La Plata Argentina

The mass spectral fragmentation of thiosemicarbazones synthesized from acetophenones has been studied by CG/MS. These carbonyl compounds exhibit chromatographic peaks which are not observed in aliphatic analogues or those synthesized from aldehydes. The analysis of the corresponding spectra has allowed structural assignment to the dimerization of gas phase neutral fragments. Theoretical calculations (DFT level) also provide evidence to support the experimental observations.

关键词： thiosemicarbazones Mass Spectrometry Analyses Dimerization of thiosemicarbazones

Synthesis and Cytotoxicity of the First Arene Ruthenium Compound Containing Two Thiosemicarbazone Ligands

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Chinese Journal of Structural Chemistry 2019年第9期38卷 1543-1548页

作者：苏炜罗志进崔浩唐兆丰李培源彭炳华 Key Laboratory of Guangxi Key Laboratory of Natural Polymer Chemistry and Physics(Nanning Normal University) Nanning530001China College of Pharmacy Guangxi University of Chinese MedicineNanning530001China

A Ru-arene compound containing two thiosemicarbazone ligands [(η6-p-cymene)Ru(TSC)2 Cl]Cl(1, TSC = benzophenone 4-methylthiosemicarbazone) has been synthesized and characterized by 1 H NMR, elemental analysis and HR-ESI mass spectrometry analysis. The molecular structure was determined by single-crystal X-ray diffraction analysis. The in vitro anticancer activities of the complex have been evaluated against two human cancer cell lines(SGC-7901, BEL-7404), and the IC50 values are 32.5 and 57 μM, respectively.

关键词： ruthenium arene thiosemicarbazones X-ray crystal diffraction cytotoxicity running head arene ruthenium compound containing TSC

Cu(II) Propionyl-Thiazole Thiosemicarbazone Complexes: Crystal Structure, Inhibition of Human Topoisomerase IIα, and Activity against Breast Cancer Cells

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Open Journal of Medicinal Chemistry 2018年第2期8卷 30-46页

作者： Edward C. Lisic Victoria G. Rand Lana Ngo Patrick Kent Jeffrey Rice Deidra Gerlach Elizabeth T. Papish Xiaohua Jiang Department of Chemistry Tennessee Technological University Cookeville TN USA Department of Chemical Engineering Tennessee Technological University Cookeville TN USA Department of Chemistry The University of Alabama Tuscaloosa Alabama USA

Two new thiosemicarbazone ligands, 2-propionylthiazole ethylthiosemicarbazone (PTZ-ETSC), and 2-propionylthiazole tert-butylthiosemicarbazone (PTZ-tBTSC), along with their two copper(II) complexes, [Cu(PTZ-ETSC)Cl] and [Cu(PTZ-tBTSC)Cl], are reported here for the first time. Once characterized by NMR and MS, these mono-anionic tridentate ligands were reacted with Cu2+ to form the square planar metal complexes [Cu(PTZ-ETSC)Cl] and [Cu(PTZ-tBTSC)Cl]. The x-ray crystal structure of the [Cu(PTZ-tBTSC)Cl] complex shows that the complex adopts a square planar arrangement around the copper(II) ion, but forms a sulfur-bridged dimer in the solid state. Both of the copper complexes displayed strong inhibition of human topoisomerase IIα at activities between 2-4 μM for [Cu(PTZ-ETSC)Cl], and between 8-10 μM for the [Cu(PTZ-tBTSC)Cl] complex. The EC50 values for the MDA-MB-231 breast cancer cell line were 82.6 μM for (PTZ-ETSC), 17.9 μM for [Cu(PTZ- ETSC)Cl], 97.8 μM for (PTZ-tBTSC), and 1.41 μM for [Cu(PTZ-tBTSC)Cl]. The EC50 values for the MCF7 breast cancer cell lines were 9.36 μM for (PTZ-ETSC), 0.13 μM for [Cu(PTZ-ETSC)Cl], 0.333 μM for (PTZ-tBTSC), and 0.093 μM for [Cu(PTZ-tBTSC)Cl].

关键词： Topoisomerase Breast Cancer thiosemicarbazones