Schiff bases and their metal Complexes: A review on the history, synthesis, and applications

Boulechfar, Chérifa; Ferkous, Hana; Delimi, Amel; Djedouani, Amel; Kahlouche, Abdesalem; Boublia, Abir; Darwish, Ahmad S.; Lemaoui, Tarek; Verma, Rajesh; Benguerba, Yacine

doi:10.1016/j.inoche.2023.110451

Cited by 121 publications

(70 citation statements)

References 132 publications

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“…We emphasize our observation that ligated salen can be reduced in situ by a simple reductant like HBpin has important implications for the catalysis presented here and beyond because (i) formation of an active Fe-salan complex could indicate that catalyst activation and active cyclotrimerization catalysis involves some element of ligand reduction and (ii) salen ligands are commonly regarded as being synthetically robust and somewhat inert; our study herein indicates otherwise. − …”

Section: Resultsmentioning

confidence: 99%

The Complex Reactivity of [(salen)Fe]₂(μ-O) with HBpin and Its Implications in Catalysis

Hood,

Lau,

Diefenbach

et al. 2023

ACS Catal.

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We report a detailed study into the method of precatalyst activation during alkyne cyclotrimerization. During these studies we have prepared a homologous series of Fe(III)-μoxo(salen) complexes and use a range of techniques including UV−vis, reaction monitoring studies, single crystal X-ray diffraction, NMR spectroscopy, and LIFDI mass spectrometry to provide experimental evidence for the nature of the on-cycle iron catalyst. These data infer the likelihood of ligand reduction, generating an iron(salan)-boryl complex as a key on-cycle intermediate. We use DFT studies to interrogate spin states, connecting this to experimentally identified diamagnetic and paramagnetic species. The extreme conformational flexibility of the salan system appears connected to challenges associated with crystallization of likely on-cycle species.

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Section: Resultsmentioning

confidence: 99%

The Complex Reactivity of [(salen)Fe]₂(μ-O) with HBpin and Its Implications in Catalysis

Hood,

Lau,

Diefenbach

et al. 2023

ACS Catal.

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“…Complexes with Schiff bases of this type have shown considerable antitumor and antimicrobial activity. [36][37][38] For this reason, we have chosen this specific group of Schiff bases as ligands for synthesizing complexes with copper and determine whether the synthesized complexes show biological activity.…”

Section: Introductionmentioning

confidence: 99%

“…The Schiff bases tetradentate ligands with two nitrogen donor and two oxygen donor atoms were very often synthesized with various substituents near the nitrogen and oxygen atoms. Complexes with Schiff bases of this type have shown considerable antitumor and antimicrobial activity 36–38 . For this reason, we have chosen this specific group of Schiff bases as ligands for synthesizing complexes with copper and determine whether the synthesized complexes show biological activity.…”

Section: Introductionmentioning

confidence: 99%

Structure, interaction with biomolecules, and cytotoxicity of copper (II) complexes chelating some Schiff base ligands

Mijatović,

Caković,

Lolić

et al. 2023

Applied Organom Chemis

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Cancer remains one of the most common diseases worldwide in terms of deaths and claims many lives every day. Transition metal complexes are candidates in the development of anticancer drugs, with cisplatin being used in chemotherapy worldwide. Copper, an endogenous metal, is known for its pronounced redox potential and nucleophilicity, especially when bound to biological molecules. Cu (II) complexes were synthesized containing ethane‐1,2‐diamine as amine moiety and pentane‐2,4‐dione and/or 1‐phenylbutane‐1,3‐dione, pentane‐2,4‐dione and/or 1,1,1‐trifluoropentane‐2,4‐dione or 1,1,1‐trifluoropentane‐2,4‐dione and/or 1‐phenylbutane‐1,3‐dione as β‐diketone moiety. Standard methods were used to confirm the structure of complexes 1–6. X‐ray crystal structure analysis characterized complex 1 containing the ligand ethane‐1,2‐diamine and pentane‐2,4‐dione. The interactions of complexes 1–6 with calf thymus DNA (ct‐DNA) were followed by electronic absorption and fluorescence spectroscopy methods and by viscosity measurements. In contrast, interaction with Salmon Sperm DNA was investigated using the electrophoretic mobility shift assay. The results indicate a moderate affinity of complexes 1–6 for binding to DNA. Gel electrophoresis also shows that the studied complexes have a concentration‐dependent interaction with DNA. Spectroscopic fluorescence techniques were used to monitor the affinity of the complexes for bovine serum albumin (BSA). Complexes 1–6 showed satisfactory binding ability for BSA. Cytotoxicity analyses were performed on the human colorectal carcinoma HCT‐116 and healthy lung fibroblast MRC‐5 cell lines, showing that complex 5 exhibited selectivity between cancer and normal cells, which is critical for drug development.

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“…This enormous outcome in the research on Schiff bases results in the demand of novel compounds with novel applications. 1 Hydroxynaphthoquinone ligands have the outstanding chelating ability due to their structural features. Lawsone, the chief constituent of Henna and a member of hydroxynaphthoquinone family, is proposed to possess enormous applications especially in biological field.…”

Section: Introductionmentioning

confidence: 99%

New homoleptic imine derivative of lawsone and its metal complexes: Preparation, characterization, in vitro and in silico biological investigation

Sheela,

Kumar,

Raman

2023

Applied Organom Chemis

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In this article, a Schiff base derivative has been prepared using 2‐hydroxy‐1,4‐naphthoquinone and 3‐amino‐1,2,4‐triazole, and consecutively, four metal complexes (Co(II), Ni(II), Cu(II) and Zn(II)) have been synthesized using this Schiff base derivative as precursor ligand. Characterization of the synthesized compounds are done by employing spectral techniques such as UV–vis, infrared (IR), nuclear magnetic resonance (NMR), mass and electron paramagnetic resonance (EPR). All these methods establish the existence of imine group and the octahedral geometry of the complexes. The synthesized complexes are evaluated for their DNA binding properties that confirm that the binding mode is intercalation. The bioactive ligand and its complexes also exhibit pronounced pharmacological activities such as antioxidant and antimicrobial activities against bacteria such as Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Salmonella typhi; fungi, namely, Aspergillus niger, Aspergillus flavus, Candida albicans and Rhizoctonia bataticola. Moreover, the compounds are examined for their density functional theory (DFT) studies using Gaussian 09 programme. Various reactivity descriptors are calculated based on the highest occupied molecular orbital–lowest unoccupied molecular orbital (HOMO‐LUMO) energies. Molecular docking is conducted with two different receptors 1BNA and 1HD2 proteins to get a wide knowledge on the in vitro biological examination and also the interaction of the compounds with different proteins.

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Schiff bases and their metal Complexes: A review on the history, synthesis, and applications

Cited by 121 publications

References 132 publications

The Complex Reactivity of [(salen)Fe]₂(μ-O) with HBpin and Its Implications in Catalysis

The Complex Reactivity of [(salen)Fe]₂(μ-O) with HBpin and Its Implications in Catalysis

Structure, interaction with biomolecules, and cytotoxicity of copper (II) complexes chelating some Schiff base ligands

New homoleptic imine derivative of lawsone and its metal complexes: Preparation, characterization, in vitro and in silico biological investigation

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Schiff bases and their metal Complexes: A review on the history, synthesis, and applications

Cited by 121 publications

References 132 publications

The Complex Reactivity of [(salen)Fe]2(μ-O) with HBpin and Its Implications in Catalysis

The Complex Reactivity of [(salen)Fe]2(μ-O) with HBpin and Its Implications in Catalysis

Structure, interaction with biomolecules, and cytotoxicity of copper (II) complexes chelating some Schiff base ligands

New homoleptic imine derivative of lawsone and its metal complexes: Preparation, characterization, in vitro and in silico biological investigation

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The Complex Reactivity of [(salen)Fe]₂(μ-O) with HBpin and Its Implications in Catalysis

The Complex Reactivity of [(salen)Fe]₂(μ-O) with HBpin and Its Implications in Catalysis