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A Green Synthesis of Carbene-Metal-Amides (CMAs) and Carboline-Derived CMAs with Potent in vitro and ex vivo Anticancer Activity.
ChemMedChem
July 2022
Department of Chemistry and Centre for Sustainable Chemistry, Ghent University, Krijgslaan 281,S-3, 9000, Ghent, Belgium.
The modularity and ease of synthesis of carbene-metal-amide (CMA) complexes based on the coinage metals (Au, Ag, Cu) and N-heterocyclic carbenes (NHCs) as ancillary ligands pave the way for the expansion of their applications beyond photochemistry and catalysis. Herein, we further improve the synthesis of such compounds by circumventing the use of toxic organic solvents which were previously required for their purification, and we expand their scope to include complexes incorporating carbolines as the amido fragments. The novel complexes are screened both in vitro and ex vivo, against several cancer cell lines and high-grade serous ovarian cancer (HGSOC) tumoroids, respectively.
View Article and Find Full Text PDFSimple Synthetic Routes to Carbene-M-Amido (M=Cu, Ag, Au) Complexes for Luminescence and Photocatalysis Applications.
Chemistry
August 2021
Department of Chemistry and Centre for Sustainable Chemistry, Ghent University, Krijgslaan 281,S-3, 9000, Ghent, Belgium.
The development of novel and operationally simple synthetic routes to carbene-metal-amido (CMA) complexes of copper, silver and gold relevant for photonic applications are reported. A mild base and sustainable solvents allow all reactions to be conducted in air and at room temperature, leading to high yields of the targeted compounds even on multigram scales. The effect of various mild bases on the N-H metallation was studied in silico and experimentally, while a mechanochemical, solvent-free synthetic approach was also developed.
View Article and Find Full Text PDFCoinage Metal N-Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications.
ChemMedChem
May 2021
Department of Chemistry, Manipal Institute of Technology, Manipal Academy of Higher Education, Manipal, 576104, Karnataka, India.
New weapons are constantly needed in the fight against cancer. The discovery of cisplatin as an anticancer drug prompted the search for new metal complexes. The successful history of cisplatin motivated chemists to develop a plethora of metal-based molecules.
View Article and Find Full Text PDFCluster Expansion versus Complex Formation: Coinage Metal Coordination to Silylated [Ge] Cages.
Inorg Chem
October 2020
Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching b. München, Germany.
Deltahedral nine-atom tetrel element Zintl clusters are promising building blocks for the straightforward solution-based synthesis of intermetalloid clusters through the reaction with organometallic compounds. Herein we report on novel coordination sites of metal--heterocyclic carbene (NHC) complexes to [Ge] clusters and unexpected cluster isomerization. We present the synthesis of a series of coinage metal-NHC complexes of silylated [Ge] clusters [NHCCu(η-Ge{Si(TMS)})] (; TMS = trimethylsilyl) and [NHCM(η-Ge{Si(TMS)})] (, M = Cu, R = Pr; , M = Cu, R = Mes; , M = Cu, R = Dipp; , M = Ag, R = Dipp; , M = Au, R = Dipp), in which the coinage metals coordinate to open rectangular cluster faces and act as additional cluster vertex atoms.
View Article and Find Full Text PDFOrganic Azide and Auxiliary-Ligand-Free Complexes of Coinage Metals Supported by N-Heterocyclic Carbenes.
Inorg Chem
February 2020
Department of Chemistry and Biochemistry , The University of Texas at Arlington, Arlington , Texas 76019 , United States.
Organic azide complexes of copper(I) and silver(I), [(SIPr)CuN(1-Ad)NN][SbF], [(SIPr)CuN(2-Ad)NN][SbF], [(SIPr)CuN(Cy)NN][SbF], and [(SIPr)AgN(1-Ad)NN][SbF] have been synthesized by using Ag[SbF] and the corresponding organic azides with (SIPr)CuBr and (SIPr)AgCl (SIPr = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene). The copper and silver organic azide complexes were characterized by various spectroscopic techniques and X-ray crystallography. Group trends of isoleptic Cu(I), Ag(I), and Au(I) organic azide complexes are presented on the basis of experimental data and a detailed computational study.
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