Substituted N-heterocyclic carbene PEPPSI-type palladium complexes with different N-coordinated ligands: Involvement in the direct C-H bond activation of heteroarenes derivatives with aryl bromide and their antimicrobial, anti-inflammatory and antioxidant activities

Slimani I., Boubakri L., Ozdemir N., Mansour L., Ozdemir İ., Gurbuz N., ...Daha Fazla

INORGANICA CHIMICA ACTA, cilt.532, 2022 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 532
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1016/j.ica.2021.120747
  • Dergi Adı: INORGANICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core
  • Anahtar Kelimeler: N-Heterocyclic carbene, PEPPSI-type palladium-NHC complexes, Direct arylation, N-Heterocyclic carbene benzimidazolium salts, Antimicrobial, Antioxidant and anti-inflammatory activities, CROSS-COUPLING REACTIONS, SUZUKI-MIYAURA REACTION, CATALYZED DIRECT ARYLATION, HECK REACTIONS, NHC, FUNCTIONALIZATION, PD, BENZOXAZOLES, RUTHENIUM, WATER
  • İnönü Üniversitesi Adresli: Evet

Özet

In this study new benzimidazolium salt as N-heterocyclic carbene precursors and their related new PEPPSI-Pd (II)-N-heterocyclic carbene (NHC) complexes 3a-e were prepared and caracterized. The structures of all compounds have been characterized by H-1 NMR, C-13 NMR, and IR spectroscopy, as well as elemental analysis techniques and Direct analysis in real time (DART)-time-of-flight mass spectrometry (TOF-MS), which support the proposed structures. Further confirmations of structural details were provided by a single-crystal X-ray. A single crystal of PEPPSI-Pd(II)-N-heterocyclic carbene (NHC) complex 3c shows that the coordination geometry around Pd slightly distorted square-planar geometry. Next, the PEPPSI-Pd(II)-N-heterocyclic carbene (NHC) complexes 3a-e were used as catalysts in the direct C-5-arylation of 2-acetyl furan and 2-acetylthiophene with various aryl bromides. These complexes exhibited moderate to high catalytic activities and gave C-H activation selectively at the C-5-position. Further, PEPPSI-Pd(II)-N-heterocyclic carbene (NHC) complexes 3a-e have been evaluated for their potential antibacterial properties against a panel of bacterial strains namely, Micrococcus luteus, Listeria monocytogenes, Salmonella Typhimurium, Staphylococcus aureus, candida albican and pseudomonas aeruginosa. In addition; these new PEPPSI-Pd(II)-N-heterocyclic carbene (NHC) complexes 3a-e were investigated for anti-oxidant activities by super oxide radical; DPPH (2,2-Diphenyl-1-picrylhydrazyl); and hydroxyl radical scavenging assays; in which most of them displayed significant antioxidant activities. Furthermore; PEPPSI-Pd(II)-N-heterocyclic carbene (NHC) complexes 3a-e were evaluated for anti-inflammatory activity by indirect haemolytic and lipoxygenase inhibition assays and revealed good activity.