Synthesis, DFT calculations, and investigation of catalytic and biological activities of back-bond functionalized re-NHC-Cu complexes

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dc.authoridBoulebd, Houssem/0000-0002-7727-8583
dc.authoridBugday, Nesrin/0000-0002-3882-035X
dc.authoridyasar, sedat/0000-0001-7285-2761
dc.authoridMANSOUR, Lamjed/0000-0002-9415-9383
dc.authorwosidBoulebd, Houssem/HMP-2883-2023
dc.authorwosidMANSOUR, Lamjed/U-3028-2017
dc.contributor.authorYagmurlu, Ayse
dc.contributor.authorBugday, Nesrin
dc.contributor.authorYasar, Seyma
dc.contributor.authorBoulebd, Houssem
dc.contributor.authorMansour, Lamjed
dc.contributor.authorKoko, Waleed S.
dc.contributor.authorHamdi, Naceur
dc.date.accessioned2024-08-04T20:56:03Z
dc.date.available2024-08-04T20:56:03Z
dc.date.issued2024
dc.departmentİnönü Üniversitesien_US
dc.description.abstractFive copper complexes (3a-e) stabilized by ring-expanded back-bond functionalized N-heterocyclic carbene ligands (re-NHCs) were produced in the glovebox 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 were utilized to completely characterize the structures of the re-Cu-NHC complexes. Furthermore, density functional theory (DFT) calculations were carried out to get further insights into their molecular geometry and CuAAC reaction mechanism. The re-NHC-Cu complexes showed high activity on the CuAAC reaction in an open-air atmosphere at rt. The Gibbs free energies as well as the optimized geometries of the intermediates and the transition states of the determining step of the reactions catalyzed by 3a, 3e, and 3b complexes were computed. Complex 3e was found to be the most efficient catalyst among these re-NHC-Cu complexes. Additionally, re-Cu-NHC complexes were investigated for their biological activities, including antiproliferative, antioxidant, AChE and TyrE inhibition, and antiparasitic activity. The results showed that the 3b, 3d, and 3e complexes possessed strong antiproliferative activity against human colon carcinoma (HCT-116) and moderate cytotoxic activity against hepatocellular carcinoma (HepG-2) cell lines. In addition, effective selective antileishmanial effects were observed for the 3e compound against both promastigotes and amastigotes stages of L. major with an IC50 value of 0.027 and 0.39 mu M mL-1, respectively. These results demonstrate that these compounds are promising candidates for the treatment of colorectal cancer and leishmaniasis. re-NHC-Cu complexes have been synthesized and used as catalyst on CuAAC reactions. imageen_US
dc.description.sponsorshipIdot;noenue University BAP [FYL-2020-2154]; King Saud University, Riyadh, Saudi Arabia [RSP2023R75]en_US
dc.description.sponsorshipThe authors extended their appreciation to the researchers supporting & Idot;noenue University BAP Project number FYL-2020-2154, and the authors extended their appreciation to the researchers supporting Project number RSP2023R75, King Saud University, Riyadh, Saudi Arabia. The supercomputing resources used in this work to perform DFT calculations were supported by the HPC of UCI-UFMC (Unite de Calcul Intesif of the University Freres Mentouri Constantine 1).en_US
dc.identifier.doi10.1002/aoc.7545
dc.identifier.issn0268-2605
dc.identifier.issn1099-0739
dc.identifier.issue7en_US
dc.identifier.scopus2-s2.0-85194001141en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1002/aoc.7545
dc.identifier.urihttps://hdl.handle.net/11616/102009
dc.identifier.volume38en_US
dc.identifier.wosWOS:001229965300001en_US
dc.identifier.wosqualityN/Aen_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.ispartofApplied Organometallic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectbiological activityen_US
dc.subjectcopperen_US
dc.subjectCuAAcen_US
dc.subjectDFTen_US
dc.subjectre-NHCen_US
dc.subjecttriazoleen_US
dc.titleSynthesis, DFT calculations, and investigation of catalytic and biological activities of back-bond functionalized re-NHC-Cu complexesen_US
dc.typeArticleen_US

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