Synthesis, Characterization and Biological Activities of Cu(II), Co(II), Mn(II), Fe(II), and UO2(VI) Complexes with a New Schiff Base Hydrazone: O-Hydroxyacetophenone-7-chloro-4-quinoline Hydrazone

Allehyani E.S., Al-Harbi S.A., Alshareef F.M., Badran A., Ibrahim M.A.

Badran A., Ibrahim M.A., Mohamed N., Mostafa M.A.

Thamaraichelvan G.

A new Schiff base 4,4’-((naphthalene-1,8-diylbis(azanylylidene))bis(methanylylidene)) diphenol (NDBDP) has been synthesized from 4-hydroxybenzaldehyde and 1,8-diaminonaphthalene and characterised by Infrared, Ultraviolet-Visible, Proton-1 Nuclear Magnetic Resonance, Carbon-13 Nuclear Magnetic Resonance and mass spectral studies. Further, the Schiff base has been complexated with Cobalt(II),Nickel(II),Copper(II) and Zinc(II). All the synthesised complexes are established as neutral complexes based on various spectral, analytical and magnetic behavioral studies. The redox property of all the metal Schiff base complexes have been explored through cyclic voltammetry analysis. Density Functional Theory (DFT) studies have been performed using GAUSSIAN09W program with B3LYP/6-31G (d,p) as the basis set to substantiate the structure of Schiff base NDBDP. The synthesized Schiff base and its transition metal complexes have been scrutinised for their biopotency namely antimicrobial, anti-inflammatory and antioxidant activities. The complex [Cu(NDBDP)2] is found to possess high antioxidant activity. The cytotoxic behaviour of the [Cu(NDBDP)2] complex was scrutinized in MCF-7 (human breast cancer cell lines) which indicate the moderate cytotoxic behaviour of the complex.

Pandey N., Krishnan D., Suresh A., Abraham J., Sheela A.

Alshaye N.A., Badran A., Ibrahim M.A.

2-Chloropyridine-3-carbonitrile derivative 1 was utilized as a key precursor to build a series of linear and angular annulated pyridines linked to a 6-hydroxy-4,7-dimethoxybenzofuran moiety. Reaction of substrate 1 with various hydrazines afforded pyrazolo[3,4-b]pyridines. Treatment of substrate 1 with 1,3-N,N-binucleophiles including 3-amino-1,2,4-triazole, 5-amino-1H-tetrazole, 3-amino-6-methyl-1,2,4-triazin-5(4H)-one and 2-aminobenzimidazole produced the novel angular pyrido[3,2-e][1,2,4]triazolo[4,3-a]pyrimidine, pyrido[3,2-e][1,2,4]tetrazolo[1,5-a]pyrimidine, pyrido[3′,2′:5,6] pyrimido[2,1-c][1,2,4]triazine and benzo[4,5]imidazo[1,2-a]pyrido[3,2-e]pyrimidine, respectively. Reaction of substrate 1 with 1,3-C,N-binucleophiles including cyanoacetamides and 1H-benzimidazol-2-ylacetonitrile furnished 1,8-naphthyridines and benzoimidazonaphthyridine. Moreover, reacting substrate 1 with 5-aminopyrazoles gave pyrazolo[3,4-b][1,8]naphthyridines. Finally, reaction of compound 1 with 6-aminouracils as cyclic enamines yielded pyrimido[4,5-b][1,8]naphthyridines. Some of the synthesized products showed noteworthy antimicrobial efficiency against all types of microbial strains. Structures of the produced compounds were established using analytical and spectroscopic tools.

Bhoopathy P., Subramani K., Sundaram Krishnamoorthy B.

The present work aims to synthesize and characterize new Schiff base metal complexes (Cu(II) and Ni(II)) derived from 4,5-Dichloro-o-phenylenediamine and 3,5-Dichloro-2-hydroxyacetophenone. The synthesized Schiff base and their complexes have been characterized with the support of more than a few standard physicochemical techniques such as elemental analysis, spectroscopic, thermal, and cyclic voltammetry studies. Further the molecular structures are ascertained by computational methods like density functional theory (DFT) methods. The newly synthesized Schiff base ligand acts as ONNO donor tetradentate chelate and coordinated through an azomethine nitrogen and phenoxo oxygen atom to the Cu(II) and Ni(II). Moreover, all the newly prepared compounds exhibit moderate biological activity such as antibacterial. The synthesized compounds were screened for their antibacterial by the disc agar diffusion method. Spectral analysis exhibits square planar geometry for Cu(II) & Ni(II) mono and binuclear complexes. The antimicrobial results indicate that the homo binuclear copper (II) complex was more active than the other mono and binuclear complexes. The theoretical DFT calculations were applied to verify the molecular geometry of chelators and their complexes. The DFT optimized geometries of the complexes are in agreement with experimental observations.

Badran A., Ahmed A., Nabeel A.I., Ibrahim M.A.

The chemical behaviour of electron deficient substrate 1 was investigated with some 1,2-bi-nucleophilic reagents. Reaction of substrate 1 with hydrazine derivatives namely hydrazine hydrate, phenylhydrazine, 7‑chloro-4-hydrazinoquinoline and 3-hydrazino-5,6-diphenyl-1,2,4-triazine led to 7-pyrazolylquinolinopyranoquinolines 2, 3, 6 and 7, respectively. These reactions proceed through γ-pyrone ring opening followed by pyrazole ring closure. Moreover, treating compound 1 with hydroxylamine hydrochloride provided 7-isoxazolylquinolino[3′,4′:5,6]pyrano[3,2-c]quinoline 8. The molecular structures were optimized utilizing DFT/B3LYP functional with 6–311G+(d,p) basis sets for all compounds. Moreover, global reactivity descriptors like chemical potential (μ), electronegativity (χ), hardness (η), softness (S) and electrophilicity index (ω) were computed to predict the chemical reactivity and kinetic stability of the synthesized compounds. The locations susceptible to attack by electrophiles and nucleophiles were examined at the same theoretical level by using molecular electrostatic potential (MEP) and condensed Fukui functions. The NMR chemical shifts were computed by the Gauge Independent Atomic Orbital (GIAO) method and compared to the experimental results. The first hyperpolarizability of the prepared compounds is higher than urea, so serves as good candidate for nonlinear optical (NLO) materials. The synthesized substances were tested for their efficacy as antimicrobial agents against a variety of bacterial and fungal species. Additionally, the present compounds revealed some antitumor activity (compounds 3 and 7 showed activity comparable to cis-platin, used as a reference drug in the assay). Furthermore, the synthesized compounds were moderately compliant with Lipinski's rule of five, suggesting that related compounds might be suitable for oral administration as medications.

Kumar R., Thakur A., Sachin, Chandra D., Kumar Dhiman A., Kumar Verma P., Sharma U.

Quinoline-based metal complexes have gained considerable attention in recent years due to their applications in various fields, including catalysis, material sciences, and medicinal chemistry. These complexes are characterized by their unique physicochemical properties, electronic arrangements, and stearic arrangements, which portray them as attractive for multiple applications. The coordination behaviour of quinoline moiety with different transition metals conceptualizes the basis of applying these complexes in diverse fields. Various reports from the scientific fraternity have focused on the same concept in past years. Herein, we have engrossed the developments and applications of quinoline-based coordination complexes. In the current review, the various aspects of quinoline-based coordination complexes have been discussed in the following five sections (i) quinoline-based coordination complexes with different transition metals that are isolated, characterized, and utilized for diverse catalytic applications; (ii) the complexes formed in situ via the coordination of quinoline-derivatives (substrates as well as ligands) with various metal ions under catalytic conditions; (iii) quinoline-based coordination complexes utilized in the field of material chemistry; (iv) biological applications of quinoline-based complexes arises due to the coordination properties; (v) and finally, the application of quinoline-based coordination complexes in sensing of various metal ions and bioimaging studies. Hence, the current compilation aims and elaborate on the coordination chemistry of quinoline-based complexes for their impact on diverse fields.

Sonawane H.R., Vibhute B.T., Aghav B.D., Deore J.V., Patil S.K.

Since the last decade, research on quinoline Schiff base metal complexes has risen substantially due to their versatile applications across many significant fields. Schiff bases are also known as azomethines, aldimines, and imines. Quinoline Schiff base-derived metal complexes are intriguing to study topics. These complexes are employed in biological, analytical, and catalytic fields. Researchers have found that Schiff bases are more biologically active when coordinated with metal ions. Research in the biological sciences has shown that heterocyclic compounds like quinoline and its derivatives are important. Because of their broad spectrum of activity, quinoline derivatives have been discovered to be effective therapeutic agents for various disorders. Even though various classical synthetic pathways mentioned in the literature are still in use, there is an urgent need for a new, more effective method that is safer for the environment, has a higher yield, generates less hazardous waste, and is easier to use. This highlights the critical need for a safe, eco-friendly approach to quinoline scaffold synthesis. This review focuses exclusively on Schiff base metal complexes derived from quinoline, fabricated and studied in the past ten years, and having anticancer, antibacterial, antifungal, antioxidant, antidiabetic, antiproliferative, DNA-intercalation, and cytotoxic activities.

Várhelyi C., Szőke Á., Sziráki L., Tomoaia-Cotișel M., Homonnay Z., Szalay R., Simon-Várhelyi M., Mereu R.-., Pokol G., Szilágyi I.-., Papp J., Mihály J., Kuzmann E.

Novel iron(II) Schiff base type complexes of [Fe(4-benzyl-2-hydroxy-propiophenone)2(o-phenylenediamine)], [Fe(ninhydrin)2(ethylenediamine)], [Fe(ninhydrin)2(1,2-propylenediamine)], [Fe(2,4,6-trihydroxy-benzyl-4-methoxyphenyl-ketone)2(ethylenediamine)] and [Fe(ninhydrin)2(1,3-propylenediamine)] have been prepared by reaction of the components dissolved in ethanol at refluxing temperature in inert atmosphere, and were characterized by mass spectrometry (MS), infrared spectrometry (IR), thermal analysis, atomic force microscopy (AFM), 57Fe Mössbauer spectroscopy, cyclic voltammetry and biological activity tests. Mössbauer spectroscopy revealed the dominant occurrence of high spin FeII besides minor or no low spin FeII in the complexes, and minor FeIII impurity phase. The cyclic voltammograms indicated peaks due to redox processes in certain complexes. In these cases the occurrence of low spin FeII was also observed. Low biological activity was experienced for some compounds. The thermal decomposition process of all complexes was performed by TG–DTG–DTA analysis in air atmosphere aiming to understand the mechanism of the mass change with increasing temperature. The importance of the current research is to find correlation between the Fe spin states, redox processes and biological activity.

Dongare G., Aswar A.

New hydrazone Schiff base N'‑(2‑hydroxy-3-methoxybenzylidene)-4-oxopiperidine-1-carbohydrazide (H2L), synthesized by the condensation reaction of 2‑hydroxy-3-methoxybenzaldehyde (HMB) and 4-oxopiperidine-1-carbohydrazide (CPH), form mononuclear complexes, [Mn(HL)(Cl)(H2O)2], [Co(HL)(Cl)(H2O)2], [Ni(HL)(Cl)(H2O)2] and [Cu(HL)(Cl) (H2O)2]. The formation of ligand was confirmed by elemental analysis, melting point, IR, 1H and 13C NMR, and ESI-Mass spectroscopy, Cu(II) complex was further examined by ESR spectroscopy. Other properties, like, molar conductance, IR, electronic spectra, magnetic susceptibility, DFT, powder X-ray diffractometer, fluorescence and thermal analysis have also been studied. Powder X-ray diffraction patterns inferred that compounds are nanocrystalline nature. Surface morphology further support this observation. All compounds show good absorption properties and in excited state at (λ334nm), the fluorochromes of the ligand and its metal (II) complexes emitted a good fluorescence emission with the resonation of 0.2 nm in (λ527–545 nm) region. The DFT B3LYP/6–311G+(d,p) calculations were carried out for the determination of the optimized structure of ligand (H2L) and its metal complexes. The frontier MOs energies data indicated good charge transfer (CT) from HOMO to LUMO. Thermal study of complexes monitored under nitrogen atmosphere led us to determine the activation parameters of various decomposition steps. On the basis of activation energy evaluated by Coat-Redfern relation, thermal stability order was found to be Ni(II)

Negru (Apostol) G., Ghinet A., Bîcu E.

In the context of a continuously increasing global cancer risk, the search for new effective and affordable anticancer drugs remains a constant demand. This study describes chemical experimental drugs able to destroy cancer cells by arresting their growth. New hydrazones with quinoline, pyridine, benzothiazole and imidazole moieties have been synthesized and evaluated for their cytotoxic potential against 60 cancer cell lines. 7-Chloroquinolinehydrazones were the most active in the current study and exhibited good cytotoxic activity with submicromolar GI50 values on a large panel of cell lines from nine tumor types (leukemia, non-small cell lung cancer, colon cancer, CNS cancer, melanoma, ovarian cancer, renal cancer, prostate cancer and breast cancer). This study provided consistent structure-activity relationships in this series of experimental antitumor compounds.

Jarullah A.A., Ali W.B., Mohammed O.W.

Views Icon Views Article contents Figures & tables Video Audio Supplementary Data Peer Review Share Icon Share Twitter Facebook Reddit LinkedIn Tools Icon Tools Reprints and Permissions Cite Icon Cite Search Site Citation Areej Ali Jarullah, Wassan B. Ali, Omnia Wael Mohammed; Synthesis and antibacterial evaluation of ligand 3-(2-amino-5-b-benzoyl-phenylimino)-1,3-dihydro-indol-2-one and its complexes with ions of Co(II), Ni(II), Cu(II), and Zn(II). AIP Conference Proceedings 31 March 2023; 2475 (1): 040012. https://doi.org/10.1063/5.0105189 Download citation file: Ris (Zotero) Reference Manager EasyBib Bookends Mendeley Papers EndNote RefWorks BibTex toolbar search Search Dropdown Menu toolbar search search input Search input auto suggest filter your search All ContentAIP Publishing PortfolioAIP Conference Proceedings Search Advanced Search |Citation Search

Dong Y., Li M., Hao Y., Feng Y., Ren Y., Ma H.

Verma S., Lal S., Narang R., Sudhakar K.