Synthesis, characterization, biological evaluation, DFT and molecular docking studies of (<i>Z</i>)-2-((2-bromo-4-chlorophenyl)imino)methyl)-4-chlorophenol and its Co(<scp>ii</scp>), Ni(<scp>ii</scp>), Cu(<scp>ii</scp>), and Zn(<scp>ii</scp>) complexes

Waziri, Ibrahim; Masena, Hlonepho M.; Yusuf, Tunde L.; Coetzee, Louis-Charl C.; Adeyinka, Adedapo S.; Muller, Alfred J.

doi:10.1039/d3nj02910g

Cited by 5 publications

(1 citation statement)

References 94 publications

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“…The Schiff base ligand, (Z)-2-(((4-chlorophenyl)imino)methyl)naphthalen-1-o1, was synthesized using a simple condensation reaction by adopting our previously reported method. [24][25][26] A solution of 2-hydroxy-1-naphthaldehyde (1.0 g, 5.8 mmol, 1 eq) in 20 mL of methanol was added to a stirring solution of 4-chloroaniline (0.74 g, 5.8 mmol, 1 eq) in 20 mL of methanol at room temperature. After which, the resulting mixture turned yellow, and three drops of formic acid were added while the stirring continued.…”

Section: Synthesis Of the Schiff Base Ligand (Hl)mentioning

confidence: 99%

Antioxidant Activity and DFT Calculations of Metal Complexes Derived from a Schiff Base Ligand: Synthesis, Characterization, and Biological Evaluation

Lawan,

Mshelia,

Mala

et al. 2024

ChemistrySelect

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Metal complexes derived from Schiff bases are known to have a wide range of applications, spanning the areas of material and medicinal sciences. Herein, a Schiff base ligand, (Z)‐2‐(((4‐chlorophenyl)imino)methyl)naphthalen‐1‐ol HL, was synthesized via a condensation reaction between 2‐hydroxy‐1‐naphthaldehyde and 4‐chloroaniline using methanol as a solvent in the presence of a catalytic amount of formic acid. The obtained ligand was further reacted with Mn(II), Ni(II), and Cu(II) using their acetate salts in a 1 : 2 stoichiometric ratio of metal to ligand to afford complexes C1–C3, respectively. Physicochemical and analytical techniques consisting of FTIR, UV‐Vis, elemental (CHN and metal content), TGA, HRMS, 1H, and 13 C NMR spectroscopy were deployed to establish the formation of the compounds. Results show that the ligand coordinated with the metal ions through the oxygen and nitrogen atoms of the phenolate and azomethine moieties, respectively, forming ON‐type complexes. Furthermore, the free ligand and its complexes were evaluated for their antioxidant activity compared to the standard (ascorbic acid) using an in vitro DPPH radical scavenging assay. From this investigation, C1 demonstrated higher radical scavenging activity than the free ligand, the complexes, and the standard (ascorbic acid). But the ligand has better scavenging activity than C2 and C3 at higher concentrations. DFT was also used to examine the electronic properties of the compounds, and the data obtained corroborated well with the experimental study.

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Section: Synthesis Of the Schiff Base Ligand (Hl)mentioning

confidence: 99%

Antioxidant Activity and DFT Calculations of Metal Complexes Derived from a Schiff Base Ligand: Synthesis, Characterization, and Biological Evaluation

Lawan,

Mshelia,

Mala

et al. 2024

ChemistrySelect

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Synthesis, Corrosion Inhibition, In Silico ADME, DFT, and Antibacterial Activity of Pyridine‐Based Schiff Base and Its Cu (II) Complex

Chaudhary,

Guragain,

Chaudhary

et al. 2024

Applied Organom Chemis

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Herein, we report the synthesis of an (E)‐N‐(pyridine‐3‐ylmethylene)pyridine‐2‐amine Schiff base (ENppa) and its Cu (II) complex (Cu‐ENppa) using 2‐aminopyridine (2APy) and pyridine‐3‐carbaldehyde (P3C). This study aimed to investigate the ADMET profiles, electronic features, antibacterial and anticorrosion activities of the synthesized ligand, and its Cu (II) complex. The compounds were characterized using various techniques, including CHN analysis, FT‐IR, 1H and 13C NMR, MALDI‐TOF MS, ICP‐MS, SEM, TGA/DTA, UV–visible spectroscopy, and powder X‐ray diffraction (PXRD). The Cu (II) ion exhibited tetrahedral geometry in the complex by coordinating with two nitrogen atoms, one from an imine group and the other from a pyridine ring. UV–visible spectroscopy and magnetic moment data also supported this geometry. TGA/DTA revealed three stages of decomposition at 141°C°C–255°C, 255°C°C–367°C, and 549°C°C–659°C, with CuO as the final residue. PXRD analysis identified ENppa and Cu‐ENppa as nanocrystallites, with crystallinities of 82% and 49%, respectively. Both compounds were highly effective in inhibiting mild steel corrosion in acidic media, with inhibition efficiencies of 97% and 98%, respective for Cu‐ENppa and ENppa. They also exhibited favorable ADME profiles, indicating potential as drug candidates for in silico ADME studies. The antibacterial activity results demonstrated promising efficacy, with Cu‐ENppa showing higher activity than ENppa.

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Exploring the Potential of N‐Benzylidenebenzohydrazide Derivatives as Antidiabetic and Antioxidant Agents: Design, Synthesis, Spectroscopic, Crystal Structure, DFT and Molecular Docking Study

Waziri,

Yusuf,

Kelani

et al. 2024

ChemistrySelect

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Hydrazone‐type Schiff bases have been widely explored owing to their therapeutic properties. These compounds are known to have antibacterial, antifungal, anticancer, and antioxidant properties, among others. In the present study, six hydrazone‐based Schiff bases (BB1–BB6) were synthesized by the reaction between derivatives of benzaldehyde and benzo hydrazide in methanolic medium in the presence of catalytic amount of formic acid. The synthesized compounds were characterized using various spectroscopic techniques such as NMR (1H, 13C, COSY, DEPT, HSQC, HMBC, and NOESY), FTIR, UV‐Vis, elemental (CHN) analysis, and high‐resolution mass spectroscopy. In addition, single crystal structures of BB2, BB4, and BB6 were obtained. In vitro antidiabetic and antioxidant potential of the compounds was evaluated on glucosidase, amylase, NO, FRAP, and DPPH assays, respectively. In all the assays, compounds BB6, BB4, and BB2 showed higher activity than the others. To further explore the chemical reactivity properties and their mechanism of action against the tested assays, DFT and molecular docking study were performed, and the results obtained reinforce the experimental study data.

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Synthesis, characterization, biological evaluation, DFT and molecular docking studies of (Z)-2-((2-bromo-4-chlorophenyl)imino)methyl)-4-chlorophenol and its Co(ii), Ni(ii), Cu(ii), and Zn(ii) complexes

Abstract: An equimolar reaction of 5-chlorosalicylaldehyde and 2-bromo-4-chloroaniline yielded the Schiff base (Z)-2-((2-bromo-4-chlorophenyl)imino)methyl)-4-chlorophenol) (HL), which was used for complexation to Co2+, Ni2+, Cu2+, and Zn2+ metal salts.

Cited by 5 publications

References 94 publications

Antioxidant Activity and DFT Calculations of Metal Complexes Derived from a Schiff Base Ligand: Synthesis, Characterization, and Biological Evaluation

Antioxidant Activity and DFT Calculations of Metal Complexes Derived from a Schiff Base Ligand: Synthesis, Characterization, and Biological Evaluation

Synthesis, Corrosion Inhibition, In Silico ADME, DFT, and Antibacterial Activity of Pyridine‐Based Schiff Base and Its Cu (II) Complex

Exploring the Potential of N‐Benzylidenebenzohydrazide Derivatives as Antidiabetic and Antioxidant Agents: Design, Synthesis, Spectroscopic, Crystal Structure, DFT and Molecular Docking Study

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