72287-26-4Relevant articles and documents
New Pd-Fe ferrocenyl antiparasitic compounds with bioactive 8-hydroxyquinoline ligands: a comparative study with their Pt-Fe analogues
Rivas, Feriannys,Medeiros, Andrea,Quiroga, Cristina,Benítez, Diego,Comini, Marcelo,Rodríguez-Arce, Esteban,Machado, Ignacio,Cerecetto, Hugo,Gambino, Dinorah
, p. 1651 - 1665 (2021)
In the search for a more effective chemotherapy for the treatment of Human African Trypanosomiasis, a disease caused by the parasiteTrypanosoma brucei, the development of ferrocenyl compounds has arisen as a promising strategy. In this work, five new Pd-Fe heterobimetallic [PdII(L)(dppf)](PF6) compounds, including 8-hydroxyquinolyl derivatives HL1-HL5 as bioactive ligands and dppf = 1,1′-bis(diphenylphosphino)ferrocene as the organometallic co-ligand, were synthesized and fully characterized in the solid state and in solution. Molecular structures of three compounds were solved by single crystal X-ray diffraction methods. The compounds displayed submicromolar or micromolar IC50values against bloodstreamT. brucei(IC50: 0.33-1.2 μM), and good selectivity towards the pathogen (SI: 4-102) with respect to mammalian macrophages (cell line J774). The new Pd complexes proved to be 2-fold to 45-fold more potent than the drug nifurtimox but most of them are less active than their Pt analogues. Potential molecular targets were studied. The complexes interact with DNA but they do not alter the intracellular thiol-redox homeostasis of the parasite. In order to understand and predict the main structural determinants on the anti-T. bruceiactivity, a search of quantitative structure-activity relationships (QSAR) was performed including all the [M(L)(dppf)](PF6) complexes, where M = Pd(ii) or Pt(ii), currently and previously developed by us. The correlation obtained shows the relevance of the electronic effects, the lipophilicity and the type of metal. According to the QSAR study, compounds with electron-withdrawing ligands, higher lipophilicity and harboring Pt would result in higherT. bruceicytotoxicity. From the whole series of [M(L)(dppf)](PF6) compounds developed, where M = Pt(ii) or Pd(ii) and HL = 8-hydroxyquinolyl derivatives, Pt-dppf-L4 (IC50= 0.14 μM, SI = 48) was selected to perform an exploratory pre-clinical study in infected mice. This hit compound lacks acute toxicity when applied to animals in the dose/regimen described and exerts an anti-proliferative effect on parasites, which extends animal survival but is not curative.
Stereospecific Synthesis of α- and β-C-Aryl-Δ2-Glycopyranosides from p-tert-Butylphenyl α-O-Δ2-Glycopyranoside via Grignard Reagents
Moineau, Christophe,Bolitt, Veronique,Sinou, Denis
, p. 1103 - 1104 (1995)
Palladium-catalysed coupling of p-tert-butylphenyl α-O-Δ2-glycopyranoside with various substituted arylmagnesium bromides provides the corresponding C-α-aryl-Δ2-glycopyranosides, while nickel-mediated reaction allows the preparation of the C-β-aryl anomers.
The thiosulfate (S2O32?) ion; a neglected but simple hetero-donor ligand towards platinum(II), palladium(II) and nickel(II)
Henderson, William,Kaewthong, Aphiwat,Saunders, Graham C.
, (2022/01/24)
Reactions of the thiosulfate ligand (as sodium thiosulfate, Na2S2O3·5H2O) with phosphine complexes of the group 10 metals Ni(II), Pd(II) and Pt(II) resulted in five neutral thiosulfate complexes, [Ni(S2O3)(dppe)] (dppe = Ph2PCH2CH2PPh2), [Pd(S2O3)(dppe)], [Pd(S2O3)(dppf)] (dppf = Fe(C5H4PPh2)2), [Pd(S2O3)(PPh3)2] and [Pt(S2O3)(PPh3)2]. X-ray structure determinations of [Pd(S2O3)(dppf)], [Pd(S2O3)(PPh3)2] and [Pt(S2O3)(PPh3)2] confirmed that thiosulfate ligand coordinates as a bidentate chelating ligand via both sulfur and oxygen donor atoms. In addition, reactions of the thiosulfate ligand with dinuclear chloride-bridged cyclopalladated complexes gave four mononuclear anionic complexes [Pd(S2O3)(damp)]? (damp = N,N-dimethylbenzylamino, (CH3)2NCH2C6H4), [Pd(S2O3)(ptpy)]? (ptpy = p-tolylpyridyl), ]Pd(S2O3)(bzpy)]? (bzpy = 2-benzylpyridyl) and [Pd(S2O3))pap)]? (pap = 2-(phenylazo)phenyl). The structure of (Ph3PCH2Ph)[Pd(S2O3)(pap)] by X-ray crystallography revealed the ability of thiosulfate ligand to cleave the bridging chloride ligand on the starting complexes by acting as an S,O-donor chelating ligand. An ESI mass spectrometric investigation showed that the coordinated thiosulfate ligand undergoes fragmentation at elevated capillary exit voltages.
Preparation method of [1, 1'-bis (diphenylphosphino) ferrocene] palladium dichloride
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Paragraph 0030-0048, (2021/02/06)
The invention discloses a preparation method of [1, 1'-bis (diphenylphosphino) ferrocene] palladium dichloride, which comprises the following steps of: (a) adding palladium powder into an aqua regia solution, heating for dissolution, adding hydrochloric acid while the solution is hot to drive nitrate, cooling, and adding an ethanol-water mixed solution for dilution; (b) dissolving 1, 1'-bis (diphenylphosphino) ferrocene (dppf) in an organic solvent in a stirring state to obtain an organic solution of 1, 1'-bis (diphenylphosphino) ferrocene; and (c) dropwise adding the solution obtained in thestep (a) into the solution obtained in the step (b), stirring for reaction, cooling, filtering, washing, draining, and carrying out vacuum drying to obtain a red [1, 1'-bis (diphenylphosphino) ferrocene] palladium dichloride complex crystal. The initial raw material palladium powder is directly used for replacing palladium dichloride, the target product is directly synthesized, the synthesis period is shortened, the reaction steps are simplified, the efficiency is improved, the production cost is reduced, the yield of the target product is larger than 99%, and the purity of the target productis larger than 99%.
