189203-95-0Relevant academic research and scientific papers
Comparative study of the antitumoral activity of phosphine-thiosemicarbazone gold(I) complexes obtained by different methodologies
Bermejo, Manuel R.,Fernández-Fari?a, Sandra,González-Barcia, Luis M.,González-Noya, Ana M.,Pedrido, Rosa,Rodríguez-Silva, Laura
, (2020)
A series of phosphino-thiosemicarbazone gold(I) dinuclear complexes obtained by two different synthetic procedures have been prepared. All the compounds have been spectroscopically characterized including single crystal X ray diffraction analysis in some of cases. [Au2(HL1)Cl2] (1), [Au2(HL2)2]Cl2 (2) and [Au2(HL3)2]Cl2 (3) have been prepared by chemical synthesis using a gold(III) salt as precursor; while [Au2(L1)2] (4), [Au2(L2)2]?2CH3CN (5) and [Au2(L3)2] (6) have been isolated from an electrochemical synthesis (HLn = 2-[2-(diphenylphosphanyl)-benzylidene]-N-R-thiosemicarbazone; HL1: R = methyl, HL2: R = methoxyphenyl, HL3: R = nitrophenyl). The in vitro cytotoxic activity of these gold(I) complexes was tested against some human tumor cell lines: HeLa 229 (cervical epithelial carcinoma), MCF-7 (ovarian adenocarcinoma), NCI-H460 (non-small-cell lung cancer) and MRC5 (normal human lung fibroblast), and the IC50 values compared with those of cisplatin. The neutral methyl-substituted complexes 1 and 4 and methoxyphenyl 5 displayed significant cytotoxic activities in all investigated cancer cell lines, being 1 and 4 the most effective. The ability of complexes 1 and 4 to induce cell death by apoptosis in Hela 229 was also investigated by fluorescence microscopy using the apoptotic DNA fragmentation as marker. These results indicated that the inhibition of cell proliferation is mainly due to an apoptotic process. In order to obtain more information about the mechanism of action of these metallocompounds, the interactions of complexes 1 and 4 with the thioredoxin reductase (TrxR) enzyme were analyzed. Both complexes exhibited a strong inhibition of the thioredoxin reductase activity.
Synthesis of heteroleptic copper(I) complexes with phosphine-functionalized thiosemicarbazones: An efficient catalyst for regioselective N-alkylation reactions
Ramachandran, Rangasamy,Prakash, Govindan,Vijayan, Paranthaman,Viswanathamurthi, Periasamy,Grzegorz Malecki, Jan
supporting information, p. 88 - 93 (2017/05/15)
Three new heteroleptic copper(I) complexes [Cu(PPh3)(PNS-H)] (1) (PNS-H?=?2-(2-(diphenylphosphino)benzylidene) thiosemicarbazone), [Cu(PPh3)(PNS-Me)] (2) (PNS-Me?=?2-(2-(diphenylphosphino)benzylidene)-4-methyl-3-thiosemicarbazone) and [Cu(PPh3)(PNS-Et)] (3) (PNS-Et?=?2-(2-(diphenylphosphino)benzylidene)-4-ethyl-3-thiosemicarbazone) have been synthesized and characterized by various spectral and analytical technique. The single-crystal X-ray diffraction study of complexes 2 and 3 confirmed the formation of complexes with Cu(I) ion, coordinated through P,N,S-donor atoms from the phosphino-thiosemicarbazone ligands. All the copper(I) complexes have been demonstrated as highly efficient catalysts for the synthesis of N-alkylated heterocyclic amine by the coupling of primary amines with alcohols at low catalyst loading, and the maximum yield was obtained up to 99%. The N-alkylation reactions were readily carried out under moderate conditions, and release of water was the only by-product. In addition, the effects of substituent's on the ligand, solvents, base and catalyst loading on the catalytic activity of the complexes have also been investigated. Advantageously, only one equivalent of the alcohol was consumed in the process.
the Golden Method : Electrochemical Synthesis Is an Efficient Route to Gold Complexes
González-Barcia, Luis M.,Romero, María J.,González Noya, Ana M.,Bermejo, Manuel R.,Maneiro, Marcelino,Zaragoza, Guillermo,Pedrido, Rosa
supporting information, p. 7823 - 7825 (2016/08/24)
Gold compounds to be obtained by the direct electrochemical oxidation of a noble metal are reported. This achievement provides an alternative procedure to obtaining neutral gold compounds with potential medical or catalytic applications.
Efficient and versatile catalysis of N-alkylation of heterocyclic amines with alcohols and one-pot synthesis of 2-aryl substituted benzazoles with newly designed ruthenium(ii) complexes of PNS thiosemicarbazones
Ramachandran, Rangasamy,Prakash, Govindan,Selvamurugan, Sellappan,Viswanathamurthi, Periasamy,Malecki, Jan Grzegorz,Ramkumar, Venkatachalam
, p. 7889 - 7902 (2014/05/20)
Ruthenium(ii) carbonyl complexes with phosphine-functionalized PNS type thiosemicarbazone ligands [RuCl(CO)(EPh3)(L)] (1-6) (E = P or As, L = 2-(2-(diphenylphosphino)benzylidene) thiosemicarbazone (PNS-H), 2-(2-(diphenylphosphino)benzylidene)-N-methylthiosemicarbazone (PNS-Me), 2-(2-(diphenylphosphino)benzylidene)-N-phenylthiosemicarbazone (PNS-Ph)) have been synthesized and characterized by elemental analysis and spectroscopy (IR, UV-Vis, 1H, 13C, 31P-NMR) as well as ESI mass spectrometry. The molecular structures of complexes 1, 2 and 6 were identified by means of single-crystal X-ray diffraction analysis. The analysis revealed that all the complexes possess a distorted octahedral geometry with the ligand coordinating in a uni-negative tridentate PNS fashion. All the ruthenium complexes (1-6) were tested as catalyst for N-alkylation of heteroaromatic amines with alcohols. Notably, complex 2 was found to be a very efficient and versatile catalyst towards N-alkylation of a wide range of heterocyclic amines with alcohols. Complex 2 can also catalyze the direct amination of 2-nitropyridine with benzyl alcohol to the corresponding secondary amine. Furthermore, a preliminary examination of performance for N,N-dialkylation of diamine showed promising results, giving good conversion and high selectivity. In addition, N-alkylation of ortho-substituted anilines (-NH2, -OH and -SH) led to the one-pot synthesis of 2-aryl substituted benzimidazoles, benzoxazoles and benzothiazoles, also revealing the catalytic activity of complex 2. This journal is the Partner Organisations 2014.
