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, Ichraf; Boubkri, L.; Özdemir, Namık; Mansour, Lamjed; Özdemır, İlknur; Gürbüz, Nevin; Yaşar, Şeyma; Sauthier, Mathieu; Hamdi, Naceur

doi:10.1016/j.ica.2021.120747

Cited by 17 publications

(15 citation statements)

References 107 publications

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“…However, they dissolved less in polar solvents such as water and ethyl alcohol, and in nonpolar solvents such as toluene. The structures of all complexes were fully characterized by using spectroscopic methods ( 1 H nuclear magnetic resonance [NMR], 13 C NMR, and Fourier-transform infrared [FTIR]) and elemental analysis techniques. All data obtained from these spectra were fully consistent with the proposed formula.…”

Section: Synthesismentioning

confidence: 99%

“…For the 13 C NMR spectra, the spectra mentioned below were observed. The characteristic carbene peaks (2-C carbene ) were observed between 162 and 164 ppm in all PEPPSI-Pd-NHC complexes 1a-e.…”

Section: Synthesismentioning

confidence: 99%

“…[2,8,9] In various catalytic systems described in the literature, significant progress has been made in different cross-linking reactions using pyridine enhanced, precatalyst, preparation, stabilization, and initiation (PEPPSI)-Pd-NHC complexes and these complexes have been reported to be highly efficient catalysts. [10][11][12][13][14][15] One of the most appealing properties of PEPPSI-Pd-NHC complexes in these studies is their stability in reaction environments under ambient conditions. [16] In the last decade, studies on the biological activities of the Pd-NHC complexes such as antileishmanial, [17] antibacterial, [17,18] antimicrobial, [18] and antitumor agents [19] have been published.…”

Section: Introductionmentioning

confidence: 99%

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New PEPPSI‐Pd‐NHC complexes bearing 4‐hydroxyphenylethyl group: Synthesis, characterization, molecular docking, and bioactivity properties

Behçet

Taslimi

Gök

et al. 2022

Archiv der Pharmazie

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Five 4‐hydroxyphenylethyl substituted pyridine enhanced, precatalyst, preparation, stabilization, and initiation‐Pd‐N‐heterocyclic carbene (PEPPSI‐Pd‐NHC) complexes are synthesized in a straightforward way. All PEPPSI‐Pd‐NHC complexes were prepared by mixing 4‐hydroxyphenylethyl substituted NHC precursors, palladium chloride, potassium carbonate, and potassium bromide in pyridine. All complexes were screened for human carbonic anhydrase I (hCA I) and hCA II, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α‐glucosidase (α‐Glu) inhibitory activities. The ChE inhibitory activities of the new PEPPSI‐Pd‐NHC complexes bearing the 4‐hydroxyphenylethyl group (1a–e) against α‐Glu, AChE, and BChE were determined by the Tao and Ellman methods. The results indicated that all the synthetic complexes exhibited potent inhibitory activities against all targets as compared to the standard inhibitors, revealed by IC50 values. The Ki values of the new PEPPSI‐Pd‐NHC complexes 1a–e for hCA I, hCA II, AChE, BChE, and α‐Glu were obtained in the ranges of 18.98–32.65, 22.95–38.13, 3.67–11.65, 4.09–9.36, 186.92–287.45 µM, respectively. Among the synthesized complexes, the most potent complexes were 1c toward hCA I and II with Ki values 18.98 and 22.95 µM, and 1d toward AChE and BChE with Ki = 3.67 and 4.09 µM, respectively.

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Section: Synthesismentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New PEPPSI‐Pd‐NHC complexes bearing 4‐hydroxyphenylethyl group: Synthesis, characterization, molecular docking, and bioactivity properties

Behçet

Taslimi

Gök

et al. 2022

Archiv der Pharmazie

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“…NHCs are known as strong σ-donors and weak π-acceptor ligands. This feature facilitates oxidative nucleophilic addition in C-H bond activation reactions [33,34]. According to Tolman electronic parameter (TEP) of [(L)Ir (CO) 2 Cl] complexes, NHCs have more strong σ-donor ability than tertiary phosphines ligands [33].…”

Section: Introductionmentioning

confidence: 99%

“…This feature facilitates oxidative nucleophilic addition in C-H bond activation reactions [33,34]. According to Tolman electronic parameter (TEP) of [(L)Ir (CO) 2 Cl] complexes, NHCs have more strong σ-donor ability than tertiary phosphines ligands [33]. As a result, in transition metal catalysis and coordination chemistry, NHCs have become the primary ligand.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular docking, and biological evaluation of 5‐alkyl(aryl)‐2‐isobutylthiazole derivatives: As α‐amylase, α‐glucosidase, and protein kinase inhibitors

Khan

Buğday

Rehman

et al. 2022

Applied Organom Chemis

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A series of 18 biologically active C5‐arylated‐2‐isobutylthiazole derivatives that were synthesized by Pd‐NHC complexes [Pd(μ‐Cl)Cl (NHC)]2, NHC = SIXyl, 2), (LCl2Pd‐NHC, L = PPh3, 3), (LCl2Pd‐NHC, L = Py, 4), (LCl2Pd‐NHC, L = 3‐CHO‐Py, 5) catalyzed C‐H bond activation reactions. The catalytic activity of Pd‐NHC complexes was examined on the C‐H bond activation reaction of 2‐isobutylthiazole. All Pd‐NHC complexes were characterized by 1H nuclear magnetic resonance specroscopy (NMR), 13C NMR, fouirer transform infrared spektroscopy (FTIR), quadrupole‐time of flying‐liquit cromotagraphy/mass spektroscopy (Q‐TOF‐LC/MS), gas chromatography–mass spectrometry (GCMS), and melting point detection technique. The physicochemical properties, pharmacokinetics, and drug‐likeness were calculated by SwissADME. PkCSM database was used to calculate toxicities profile. All the products (6a–6s) were additionally assessed in vitro for their antidiabetic potential using α‐amylase and α‐glucosidase inhibitory activities. The protein kinase activity was performed to evaluate their anticancer activities. All the compounds possess drug‐like characters as they followed Lipinski's rule of five (RO5). Almost all the compounds showed no to fewer toxicities. In addition, other than the compounds, that is, 6a, 6b, 6c, 6m, 6n, 6p, and 6s, the rest of the compounds showed good α‐glucosidase inhibitory potential (IC50 7.17 ± 0.201 to 74.08 ± 0.244 μg/ml) when compared with acarbose standard (IC50 16.59 ± 0.135 μg/ml). All compounds had moderate to good inhibitory potential against the α‐amylase enzyme, with IC50 values ranging from 12.00 ± 0.289 to 76.15 ± 0.477 μg/ml. Eleven analogs (6e, 6f, 6g, 6h, 6j, 6k, 6l, 6n, 6o, 6p, and 6r) showed good to moderate activity. Seven analogs (6a, 6b, 6c, 6d, 6i, 6m, and 6s) showed no α‐amylase inhibitory activity. The protein kinase inhibition potential was determined for the first time, and the compounds 6d, 6e, 6f, 6h, 6k, 6p, and 6r depicted activity with the zone of inhibition in the range of 9 ± 1.3 to 19 ± 1.5 mm. The ligands and active site binding interactions of α‐glucosidase, α‐amylase, and protein kinase enzymes were also studied using molecular modeling.

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Synthesis and cytotoxic activity of PEPPSI complexes based on 2-R-5,6-dihydro[1,2,4]triazolo[3,4-a]isoquinolin-2-ium salts

Ermakova,

Gracheva,

Maiorova

et al. 2024

Russ Chem Bull

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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

Cited by 17 publications

References 107 publications

New PEPPSI‐Pd‐NHC complexes bearing 4‐hydroxyphenylethyl group: Synthesis, characterization, molecular docking, and bioactivity properties

New PEPPSI‐Pd‐NHC complexes bearing 4‐hydroxyphenylethyl group: Synthesis, characterization, molecular docking, and bioactivity properties

Synthesis, molecular docking, and biological evaluation of 5‐alkyl(aryl)‐2‐isobutylthiazole derivatives: As α‐amylase, α‐glucosidase, and protein kinase inhibitors

Synthesis and cytotoxic activity of PEPPSI complexes based on 2-R-5,6-dihydro[1,2,4]triazolo[3,4-a]isoquinolin-2-ium salts

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