Akademik Veri Yönetim Sistemi
Applied Organometallic Chemistry, cilt.7545, ss.7545-7561, 2024 (Hakemli Dergi)
Five copper complexes (3a–e) stabilized by ring-expanded back-bond functio-nalized N-heterocyclic carbene ligands (re-NHCs) were produced in the glove-box by reacting free re-NHC with CuI precursor. The potential of these re-NHC-Cu complexes as catalysts on the synthesis of mono- and di-(1,-4-disubstituted-1,2,3-triazoles) by Cu-catalyzed azide–alkyne cycloaddition(CuAAC) reactions was investigated. Various spectroscopic approaches wereutilized to completely characterize the structures of the re-Cu-NHC complexes. Furthermore, density functional theory (DFT) calculations were carried out toget further insights into their molecular geometry and CuAAC reaction mech-anism. The re-NHC-Cu complexes showed high activity on the CuAAC reac-tion in an open-air atmosphere at rt. The Gibbs free energies as well as theoptimized geometries of the intermediates and the transition states of thedetermining step of the reactions catalyzed by 3a, 3e, and 3b complexes werecomputed. Complex 3e was found to be the most efficient catalyst among thesere-NHC-Cu complexes. Additionally, re-Cu-NHC complexes were investigatedfor their biological activities, including antiproliferative, antioxidant, AChEand TyrE inhibition, and antiparasitic activity. The results showed that the 3b,3d, and 3e complexes possessed strong antiproliferative activity against humancolon carcinoma (HCT-116) and moderate cytotoxic activity against hepatocel-lular carcinoma (HepG-2) cell lines. In addition, effective selective antileish-manial effects were observed for the 3e compound against both promastigotesand amastigotes stages of L. major with an IC 50 value of 0.027 and0.39 μM mL1, respectively. These results demonstrate that these compoundsare promising candidates for the treatment of colorectal cancer and leishmaniasis.