Synthesis, spectral characterization, density functional theory studies, and biological screening of some transition metal complexes of a novel hydrazide–hydrazone ligand of isonicotinic acid

Tolan, Dina A.; Kashar, Tahani I.; Yoshizawa, Kazunari; El‐Nahas, Ahmed M.

doi:10.1002/aoc.6205

Cited by 25 publications

(24 citation statements)

References 82 publications

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“…3 T 1g (P) (ν 3 ) transitions, respectively. [53,58] The magnetic moment value of Ni(II) complex (3.45 B.M.) along with its electronic transition bands confirms the high-spin octahedral environment around Ni(II) ions.…”

Section: Electronic Spectra and Magnetic Moment Studiesmentioning

confidence: 68%

“…[51,52] However, the spectrum of Cu(II) perchlorate complex (6) displays a splitted band at 1079, 1075, and 622 cm À1 , compatible with a monodentate chelation of perchlorate group. [53][54][55] The previously mentioned data along with the absence of vibrational modes of ÀOH group are ruling out tautomerism and confirm the neutral behavior of the ligand that acts as a bidentate one through amino nitrogen and carbonyl oxygen atoms.…”

Section: Infrared Spectral Studiesmentioning

confidence: 77%

“…Furthermore, the ligand spectrum displays signals within range δ (6.07-7.18 ppm), corresponding to aromatic ring protons. [53,55,60] These signals are almost in the same position in Cd(II) complex (Table 3). The absence of ÀOH signal in the ligand spectrum gathered with IR spectral data establishes the ligand neutral coordination mode.…”

Section: H 1 Nmr Spectral Investigationmentioning

confidence: 78%

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Spectral studies, thermal investigations, and anticancer activity of some divalent metal complexes derived from 2‐(4‐bromophenylamino)acetohydrazide ligand

Emara

El‐Sayed

Khalaf‐Allah

et al. 2022

Applied Organom Chemis

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A series of biologically active metal complexes was yielded from the reactions of 2‐(4‐bromophenylamino)acetohydrazide ligand (HL) with Co(II), Ni(II), Cu(II), Cd(II) chlorides, CuBr2, Cu(CH3COO)2, and Cu(ClO4)2 salts. The structure and stereochemistry of the afforded complexes were elucidated by means of elemental analyses, molar conductance, magnetic susceptibility, thermal analyses (TG/DTG), and spectral techniques (mass, IR, UV‐Vis, and 1H NMR). Elemental analyses along with molar conductance data demonstrated that all metal complexes are nonelectrolyte and were formed with 1L:1M, 1L:2M, and 2L:1M stoichiometry. IR spectral data provided an evidence for the neutral bidentate behavior of the hydrazide ligand toward metal ions via carbonyl oxygen and amino nitrogen atoms (ON donor). Magnetic susceptibility along with electronic absorption spectral results authenticated that all complexes have an octahedral geometry except, CuCl2 complex (3), which possessed a square planar one. The hydrazide ligand and some of its synthesized metal complexes were screened in vitro for their antitumor and apoptotic activity. The results showed that CuBr2 complex (4) has promising anticancer activities against breast MCF7, liver HepG2, and colorectal HCT 116 cancerous cells through induction of proapoptotic gene (Bax) and inhibit the antiapoptotic gene (Bcl‐2), thus increase the Bax/Bcl‐2 ratio. Moreover, these newly synthesized compounds were most potent and can be used as a therapeutic chemoprevention against these cancerous cells compared with doxorubicin (DOX), the currently available anticancer drug against solid tumors.

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Section: Electronic Spectra and Magnetic Moment Studiesmentioning

confidence: 68%

Section: Infrared Spectral Studiesmentioning

confidence: 77%

Section: H 1 Nmr Spectral Investigationmentioning

confidence: 78%

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Spectral studies, thermal investigations, and anticancer activity of some divalent metal complexes derived from 2‐(4‐bromophenylamino)acetohydrazide ligand

Emara

El‐Sayed

Khalaf‐Allah

et al. 2022

Applied Organom Chemis

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“…In evaluating the antioxidant activity of MD, one has to also consider that pyridines are very good coordinating ligands and therefore it is highly likely that MD forms chelates with trace metals [5,6]. Previous studies showed that the presence of transition metals such as Cu(I) can produce hydroxyl radicals via the Fenton-like reaction (1.1) [7][8][9][10][11]:…”

Section: Introductionmentioning

confidence: 99%

Theoretical insights into the antiradical activity and copper-catalysed oxidative damage of mexidol in the physiological environment

et al. 2022

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Mexidol ( MD , 2-ethyl-6-methyl-3-hydroxypyridine) is a registered therapeutic agent for the treatment of anxiety disorders. The chemical structure suggests that MD may also act as an antioxidant. In this study, the hydroperoxyl radical scavenging activity of MD was studied to establish baseline antioxidant activity, followed by an investigation of the effect of MD on the copper-catalysed oxidative damage in biological systems, using computational methods. It was found that MD exhibits moderate radical scavenging activity against HOO • in water and pentyl ethanoate solvents following the single electron transfer and formal hydrogen transfer mechanisms, respectively. MD can chelate Cu(II), forming complexes that are much harder to reduce than free Cu(II): MD chelation completely quenches the Cu(II) reduction by ascorbic acid and suppresses the rate of reduction reaction by O 2 ⋅ − that are the main reductants of Cu(II) in biological environments. Therefore, MD exerts its anti-HO • activity primarily as an OIL-1 inhibitor.

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“…Furthermore, they are important compounds for drug design, as possible ligands for metal complexes, organo-catalysis and also for the syntheses of heterocyclic compounds [10]. In recent years, a lot of biologically important hydrazide-hydrazones derivatives have been synthesized from different carbonyl compounds [11] [12] [13] [14] [15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic, Molecular Modeling and Anti-Fungal Studies of Some Divalent Metal Complexes of 4-Hydroxyacetophenone Isonicotinoyl Hydrazone

Toh-Boyo¹,

Njong²,

Babette³

et al. 2021

OJIC

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A novel ligand N-4-hydroxyacetophenone isonicotinoyl hydrazone and its manganese(II) and nickel(II) metal complexes have been synthesized. The synthesized Schiff base and its metal complexes have been characterized by physical state determination, melting point and solubility measurements in different solvents, infrared, proton nuclear magnetic resonance, mass spectrometric and powder X-ray spectroscopic techniques. The thermal properties of the prepared compounds were obtained from TG/DTG measurements. On the basis of the analytical techniques, the ligand was found to be bidentate in nature coordinating to the metal ions through the azomethine nitrogen and carbonyl oxygen atoms leading to distorted octahedral geometries of the metal complexes which were modeled using MM2 force field. The ligand and its metal(II) complexes were evaluated for antifungal activity against Aspergillus fumigatus, Aspergillus niger, Candida albicans and Rhizopus stolonifera. The antifungal evaluation results revealed an enhanced activity upon coordination of the ligand with the metal(II) ions. The activity of the metal complex to the tested fungal strains was in the order Ni(II) > Mn(II).

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Synthesis, spectral characterization, density functional theory studies, and biological screening of some transition metal complexes of a novel hydrazide–hydrazone ligand of isonicotinic acid

Abstract: Highlights• A new hydrazide-hydrazone ligand of isonicotinic acid was synthesized. • Seven mononuclear Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), and Hg(II) complexes of the new ligand were prepared and characterized by different tools.

Cited by 25 publications

References 82 publications

Spectral studies, thermal investigations, and anticancer activity of some divalent metal complexes derived from 2‐(4‐bromophenylamino)acetohydrazide ligand

Spectral studies, thermal investigations, and anticancer activity of some divalent metal complexes derived from 2‐(4‐bromophenylamino)acetohydrazide ligand

Theoretical insights into the antiradical activity and copper-catalysed oxidative damage of mexidol in the physiological environment

Synthesis, Spectroscopic, Molecular Modeling and Anti-Fungal Studies of Some Divalent Metal Complexes of 4-Hydroxyacetophenone Isonicotinoyl Hydrazone

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