A novel azo‐azomethine benzoxazole‐based ligand and its transition metal (II), (III), (IV) complexes: Synthesis, characterization, theoretical studies, biological evaluation, and catalytic application

Abstract

This work describes the synthesis of a novel multiple dentation azo-Schiff base dye 2- ((3-((5-chlorobenzo[d]oxazol-2-yl)diazenyl)-4-hydroxybenzylidene) amino)pyridin-3-ol (H 2 L) based mixed heterocyclic bnzoxazole and pyridine moieties in facile two successive steps approach. Firstly is the synthesis of start azo dye 3- ((5-chlorobenzo[d]oxazol-2-yl)diazenyl)-4-hydroxybenzaldehyde (CBOAHB) followed by condensation with 3-hydroxy 2-amino pyridine. It's novel binuclear Ni (II), Cu (II), Ru (III), and Zr (IV) 2:1 metal-to-ligand stoichiometric complexes were synthesized and characterized via various spectroscopic and analytical techniques. The data showed the paramagnetic Ni 2+ complex has tetrahedral geometry, while the Cu 2+ , Ru 3+ , and diamagnetic Zr 4+ complexes have octahedral geometrical structures. Data of the crystallinity, morphology, and average particle size showed that Cu 2+ and Ru 3+ complexes were formed at the nanoscale. The geometrical structures according to 3D molecular modeling are in good agreement with those proposed by the experiments. The azo start CBOAHB, H 2 L, and its metal complexes have been examined for their biological and catalytic features. The Zr 4+ complex manifested higher antibacterial activity against Staphylococcus aureus (S. aureus), the ligand H 2 L exhibited higher antibacterial activity against Escherichia coli (E. coli), and the Ni 2+ complex showed higher antifungal activity against Candida albicans (C. Albicans). The anticancer activity was evaluated against human hepatocellular carcinoma (HepG-2), colorectal carcinoma (HCT-116), and human breast carcinoma (MCF-7). The ligand H 2 L has very strong cytotoxicity toward HepG-2 cells, Ni (II) complex has the strongest cytotoxicity against HCT-116 cells and Zr (VI) has the strongest cytotoxicity against MCF-7 cells. The findings of antioxidant activity are in perfect accord with those obtained from anticancer. The heterogeneous catalytic activity was examined for the reduction of Direct Blue 14 dye. Ru (III) complex and Cu (II) complex achieved the highest catalytic activity with the highest degradation % and within a very short time did not exceed 3 min.

Synthesis, Characterization, in silico DFT, Molecular docking, ADMET Profiling Studies and Toxicity Predictions of Ag(I) Complex Derived from 4‐Aminoacetophenone

“…Moreover, the spectra of the free ligand exhibit additional spectral bands at (3126 and 3046) cm −1 and (3120 and 2924) cm −1 correspond to υ(C‐H armatic ) and υ(C‐H aliphatic ) for (DMPDE) and Ag(I) complex respectively. The appearance of stretching vibration is characterized by υ(C−H), It is confirmed that the ligand conforms to an azo structure does not form a hydrazo structure and reacts with metal ions through the azo moiety [52] . Triplet bands were also noticed at (1674, 1599, 1491) and (1675, 1601, 1495) cm −1 for DMPDE and Ag(I) complex were related to υ(C=O), υ(C=N) and υ(N=N).…”

“…The appearance of stretching vibration is characterized by υ(CÀ H), It is confirmed that the ligand conforms to an azo structure does not form a hydrazo structure and reacts with metal ions through the azo moiety. [52] Triplet bands were also noticed at (1674, 1599, 1491) and (1675, 1601, 1495) cm À 1 for DMPDE and Ag(I) complex were related to υ(C=O), υ(C=N) and υ(N=N). In the spectrum of the azo ligand, there are two feature moiety pairs: υ(N=N) and υ(À CÀ N=NÀ CÀ ).…”

Synthesis, Characterization, Antimicrobial, Density Functional Theory, and Molecular Docking Studies of Novel Mn(II), Fe(III), and Cr(III) Complexes Incorporating 4-(2-Hydroxyphenyl azo)-1-naphthol (Az)

“…In the case of the CrAz 2 complex, the electronic spectrum band at 615 nm was connected to the transition of 4 A 2g (F) → 4 T 2g (F) in the octahedral geometry complex. 52 The 3.84 B.M magnetic moment found for the CrAz 2 complex may be described by the occurrence of a d 3 (t 2g…”

“…Research in the fields of biology, electrochemistry, and analysis may all make use of these substances in a variety of different ways . Because of their potential cytotoxicity as well as their antibacterial, antifungal, and antioxidant capabilities, they have garnered a lot of studies. , There has been a significant amount of research done on the production of metal­(II) complexes of azo compounds, as well as their biological activity. , Because their azo group possesses powerful medicinal properties, azo dyes are advantageous chelating agents for a variety of metal ions, , due to the azo group of these dyes. In addition to this, it has been demonstrated that azo metal complexes can be beneficial as metal anticorrosion agents and as thermally stable optical storage devices, , …”

Zeolite-encapsulated copper(ii) complexes with NNO-tridentate Schiff base ligands: catalytic activity for methylene blue (MB) degradation under near neutral conditions

“…12–14 Copper-based complexes acting as alternatives to expensive metals, have been employed in the degradation of dyes, and exhibit superior reactivity. 15–17 However, there are several disadvantages to homogenous catalysts that prevent their application, such as the inability to achieve easy separation and high recyclability of these catalysts. To overcome these drawbacks, heterogenization of catalysts has occurred in the last few years.…”