1058159-10-6Relevant academic research and scientific papers
Tailored ligand acceleration of the cu-catalyzed azide-alkyne cycloaddition reaction: Practical and mechanistic implications
Presolski, Stanislav I.,Hong, Vu,Cho, So-Hye,Finn
, p. 14570 - 14576 (2010)
Tris(heterocyclemethyl)amines containing mixtures of 1,2,3-triazolyl, 2-benzimidazoyl, and 2-pyridyl components were prepared for ligand acceleration of the copper-catalyzed azide-alkyne cycloaddition reaction. Two classes of ligands were identified: thos
Synthesis, characterization and catalytic activity of novel ruthenium complexes bearing NNN click based ligands
Sole, Roberto,Bortoluzzi, Marco,Spannenberg, Anke,Tin, Sergey,Beghetto, Valentina,De Vries, Johannes G.
, p. 13580 - 13588 (2019/09/30)
Novel air stable ruthenium(ii) complexes bearing tridentate ligands bis((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine (L1), 1-(1-benzyl-1H-1,2,3-triazol-4-yl)-N-(pyridin-2-ylmethyl)methanamine (L2) or 2-(4-phenyl-1H-1,2,3-triazol-1-yl)-N-(pyridin-2-ylmethyl)ethan-1-amine (L3) were synthesised. The nitrogen based ligands were easily prepared by virtue of click chemistry using cheap and commercially available reagents. The ruthenium complexes were obtained by heating the Ru(PPh3)3Cl2 precursor and the tridentate NNN ligand in toluene under reflux for 2 hours, achieving yields of 82-87%. These complexes were fully characterized by means of NMR, FT-IR and high resolution ESI spectroscopy. The crystal structure of one of the complexes was determined. These complexes showed excellent activity and selectivity in the hydrogenation of ketones and aldehydes. DFT calculations show that complex 3 may react through an outer-sphere catalytic cycle rather than via an inner-sphere mechanism.
Click-to-chelate : Design and incorporation of triazole-containing metal-chelating systems into biomolecules of diagnostic and therapeutic interest
Struthers, Harriet,Spingler, Bernhard,Mindt, Thomas L.,Schibli, Roger
experimental part, p. 6173 - 6183 (2009/05/27)
The site-specific conjugation of metal chelating systems to biologically relevant molecules is an important contemporary topic in bioinorganic and bioorganometallic chemistry. In this work, we have used the Cu'-catalyzed cycloaddition of azides and terminal alkynes to synthesise novel ligand systems, in which the 1,2,3-triazole is an integral part of the metal chelating system. A diverse set of bidentate alkyne building blocks with different aliphatic and aromatic backbones and various donor groups were prepared. The bidentate alkynes were reacted with benzyl azide in the presence of a catalytic amount of Cu 1 to form tridentate model ligands. The chelators were reacted with [ReBr3(CO)3]2- to form well-defined and stable complexes with different overall charges, structures and hydrophilicities. In all cases tridentate coordination of the ligands, including through N3 of the 1,2,3-triazole ring, was observed. The ligand systems could also be quantitatively radiolabelled with the precursor [99mTc (H 2O)3(CO)3]+ at low ligand concentrations. Similarly the alkynes were reacted with an azido thymidine derivative to form a series of compounds, which could be radiolabeled in situ to form single products. Subsequent incubation of the neutral and cationic organometallic 99mTc thymidine derivatives with human cytosolic thymidine kinase, a key enzyme in tumour proliferation, revealed that only the neutral compounds maintained substrate activity towards the enzyme. Bioconjugation, radiolabelling and enzymatic reactions were successfully performed in a matter of hours. Thus, click chemistry provides an elegant method for rapidly functionalising a biologically relevant molecule with a variety of efficient metal chelators suitable for (radiolabelling with the M(CO) 3 core (M = 99mTc, Re), to offer new potential for technetium-99m in clinical and preclinical tracer development.
