Tetrameric copper(II) metallocyclic complex bearing an amino acid derived Schiff base ligand: Structure, catalytic and antioxidant activities

Soberanes, Yedith; López-Gastélum, Karla-Alejandra; Moreno-Urbalejo, Jonathan; Salazar-Medina, Alex J.; Estrada-Montoya, María del Carmen; Sugich-Miranda, Rocio; Hernández-Paredes, Javier; González‐Córdova, Aarón F.; Vallejo-Córdoba, Belinda; Sotelo‐Mundo, Rogerio R.; Velázquez-Contreras, Enrique F.; Rocha-Alonzo, Fernando

doi:10.1016/j.inoche.2018.06.010

Cited by 9 publications

(4 citation statements)

References 17 publications

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“…glycine, DL‐a‐alanine, DL‐phenylalanine, DL‐valine, tryptophan and alanine), are well documented as dibasic tri‐O,N,O‐donor chelate reagents specifically with copper (II) ions forming high stable Cu (II)‐complexes . The vacant fourth coordination site of Cu 2+ ion in the complex would be occupied by neutral molecules, for example water, urea and pyridine, or anionic species, for example cyanate or thiocyanate anions in a geometry of square planar, square‐pyramidal or square‐bipyramidal, with a monomeric, dimeric, oligomeric or polymeric structure . The different bridging structures with mixed ligands of Cu (II)‐amino acid Schiff base complexes were also formed previously…”

Section: Introductionmentioning

confidence: 99%

Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Al-Hussein

Adam

2020

Applied Organom Chemis

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N‐Salicylidene amino acid Schiff base sodium sulfonate salt, as a tridentate dibasic chelating ligand, was obtained from the common condensation of salicylaldehyde‐5‐sodium sulfonate with tyrosine (HPST). The internal formed ligand coordinated to Cu2+ ion in an aqueous media affording new Cu (II)‐complex (Cu‐PST), which characterized by various physico‐chemicals spectral tools. The mononuclear complex was evaluated as a homogeneous and heterogeneous catalyst in the (ep)oxidation protocols of 1,2‐cyclooctene and benzyl alcohol. Heterogeneously, Cu‐PST was immobilized on Fe3O4‐SiO2, as nanoparticles. The heterogeneous catalyst was characterized by infrared, X‐ray diffraction, scanning electron microscopy, transmission electron microscopy, energy‐dispersive spectroscopy, Brunauer−Emmett−Teller and magnetism. Homogeneously, the temperature, solvent and oxidant influences were examined in the catalytic reactions to realize the best reaction conditions. Cu‐catalyst exhibited better catalytic performance in the (ep)oxidation processes homogeneously than that in the heterogeneous phase at 80°C for 2 hr in acetonitrile. Reusability of the homogeneous catalyst was for a maximum of three times in the (ep)oxidation reaction, whereas the heterogeneous catalyst was active for six times. A mechanistic pathway was proposed for both catalysts, comparatively.

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Section: Introductionmentioning

confidence: 99%

Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Al-Hussein

Adam

2020

Applied Organom Chemis

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“…Metallocyclic structures are not common for amino acid Schiff base ligands. This is one of the few reports of this kind of structure [ 24 ]. Copper(II) centers are attached to two ligand units: the first ligand ( 2 ) coordinates the copper(II) ion through the imine nitrogen atom (N1), the phenolic oxygen atom (O3) and one of the carboxylate oxygen atoms (O1); a second ligand ( 2 * ) completes the coordination sphere through one of the carboxylate oxygen atoms (O2 *) and acts as a tridentate ligand, coordinating a second copper(II) center through N1 *, O3 *, and O1 *, atoms; this pattern continues until a four-metal cycle is completed.…”

Section: Resultsmentioning

confidence: 96%

Mononuclear and Tetranuclear Copper(II) Complexes Bearing Amino Acid Schiff Base Ligands: Structural Characterization and Catalytic Applications

et al. 2021

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Two new glycine-Schiff base copper(II) complexes were synthesized. Single crystal X-ray diffraction (SCXRD) allowed us to establish the structure of both complexes in the solid state. The glycine-Schiff base copper(II) complex derived from 2′-hydroxy-5′-nitroacetophenone showed a mononuclear hydrated structure, in which the Schiff base acted as a tridentate ligand, and the glycine-Schiff base copper(II) complex derived from 2′-hydroxy-5′-methylacetophenone showed a less common tetranuclear anhydrous metallocyclic structure, in which the Schiff base acted as a tetradentate ligand. In both compounds, copper(II) had a tetracoordinated square planar geometry. The results of vibrational, electronic, and paramagnetic spectroscopies, as well as thermal analysis, were consistent with the crystal structures. Both complexes were evaluated as catalysts in the olefin cyclopropanation by carbene transference, and both led to very high diastereoselectivity (greater than 98%).

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“…ROS (reactive oxygen species) were suspected to be the cause of the bacterial inhibition, so oxidation tests were performed with ABTS (2,2 -azinobis-3-ethylbenzothiazoline-6-sulfonic acid) and copper compounds (C4.1, C6.1, C2.2, C8.2, C9.2 and C11.2), and compared to sodium persulfate, in the dark or under a white lamp (60 watt). The result produced absolutely no oxidized ABTS species, And, as mentioned in the literature, copper Schiff-based compounds can exhibit antioxidant activity [23][24][25]. The antioxidant activity of the best antibacterial compounds C4.1, C6.1, C2.2, C8.2, C9.2 and C11.2 was kinetically tested against the oxidation of ABTS to the ABTS + radical [26] by sodium persulfate (Figure 2).…”

Section: Antioxidant Activitymentioning

confidence: 90%

Synthesis, Identification and Antibacterial Activities of Amino Acid Schiff Base Cu(II) Complexes with Chlorinated Aromatic Moieties

Otani

Fayeulle

Nakane

et al. 2022

Applied Microbiology

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Amino acid Schiff base Cu(II) complexes were synthesized under microwave irradiation using methanol as a solvent, to maximize the best conditions to obtain the attained compounds, containing aromatics possessing no, one or two chlorine atoms. The compounds’ antibacterial activities were tested against Gram-positive and Gram-negative bacteria, and the most active were tested for their antioxidant activities, and as E. coli, in particular, was found to be sensitive to these compounds, their interaction with this bacterium was investigated. It was found that, depending on the amino acid used for the formation of the Schiff base ligand, its LogPo/w mono-chlorinated or bis-chlorinated compounds are the most efficient against the tested bacteria.

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Tetrameric copper(II) metallocyclic complex bearing an amino acid derived Schiff base ligand: Structure, catalytic and antioxidant activities

Cited by 9 publications

References 17 publications

Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Catalytic evaluation of copper (II)N‐salicylidene‐amino acid Schiff base in the various catalytic processes

Mononuclear and Tetranuclear Copper(II) Complexes Bearing Amino Acid Schiff Base Ligands: Structural Characterization and Catalytic Applications

Synthesis, Identification and Antibacterial Activities of Amino Acid Schiff Base Cu(II) Complexes with Chlorinated Aromatic Moieties

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