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Publication Date: 2024
Monatshefte fur Chemie (00269247)155(10)pp. 967-976
The reaction between symmetric ylides RC6H4C(O)CH = PPh2(CH2)2PPh2 = CHC(O)C6H4R (Y) (R = OMe, F) and [PdCl2(COD)] (COD = 1,5-cyclooctadiene) led to the formation of palladacycle complexes, whose structures were investigated using CHN, NMR, and IR identification methods. Additionally, the precise structure of Y was confirmed through X-ray diffraction analysis. The structures of these complexes were also examined theoretically using Density Functional Theory at the BP86/def2-SVP level. The nature of the bond between the Y and PdCl2 moieties in the synthesized complexes was studied using Energy Decomposition Analysis, Natural Bond Orbital analysis, and their associated natural orbitals for chemical reactivity. The results obtained suggest the formation of palladacycles through the coordination of the ylide to the metal, mediated by ylidic carbon. Finally, the anticancer activity of these complexes as antiproliferative agents against breast carcinoma (MCF-7), Human cervix (HeLa), gastric carcinoma (AGS), and non-small lung carcinoma (A549) cell lines was investigated using the micro-culture (MTT) assay. Graphical abstract: (Figure presented.) © Springer-Verlag GmbH Austria, part of Springer Nature 2024.
Publication Date: 2023
Journal of Molecular Structure (00222860)1276
A new symmetrical macroacyclic Schiff base ligand (H2L) was prepared by the condensation reaction of 2-(4-(2-aminophenyl)piperazin-1-yl)benzeneamine and 2-hydroxy-5-nitro-benzaldehyde which was then used to synthesize the Co(II), Ni(II) and Cu(II) complexes. The new compounds were characterized by Mass spectrometry, IR, 1H NMR and 13C NMR spectroscopy and elemental analyses. The single crystal X-ray structural analysis of [CoL] showed that the Cobalt atom was in a slightly distorted trigonal prismatic environment coordinated by the four amine nitrogen atoms and two phenol oxygen atoms of the ligand; the nitro groups are not coordinating to the metal atom. The in vitro antioxidant attributes of the synthesized compounds were evaluated, using DPPH free radical scavenging with the lowest IC50 reported for [CuL]. The cytotoxicity of the compounds was also evaluated against A-549 lung adenocarcinoma cells, which showed the H2L and [CuL] were more effective than the other two compounds. NBO, EDA, and EDA-NOCV studies were used to look at the type of metal–ligand interactions in these complexes. © 2022
Publication Date: 2022
Journal of Molecular Structure (00222860)1251
Herein, we aim at preparing 15-membered-ring symmetrical pentaaza macrocyclic Schiff base complexes using a template approach, based on the condensation reaction of an amine containing piperazine moiety, 2,2-(piperazine1,4-diyl)dianiline, and 2,6-diacetylpyridine in 1:1 mol ratio while Cd(II), Mn(II) and Zn(II) metal ions are present. Moreover, FT-IR, mass spectrometry, magnetic susceptibility measurements, UV–Vis and, 1H and 13C NMR spectroscopy were used to characterize these Schiff base complexes. Besides, the structure of [C25H25N5CdBr][ClO4] was determined using a single crystal X-ray structural analysis. Being in a pentagonal planar coordination environment, the Cd atom is surrounded by a Br atom in the apical position and 5 nitrogen atoms in the pentagonal plane. We also aimed at screening the synthesized complexes to investigate their antioxidant activities applying the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging assay. also, their bactericidal activity was evaluated using a paper disk diffusion method against both Gram-negative and Gram-positive bacteria, revealing a strong antioxidant activity and moderate effectiveness against all the tested bacteria. Finally, it is worth mentioning that the complex cytotoxicity was evaluated against MCF-7 (breast) and A549 (lung) adenocarcinoma cells. Generally, as compared to [ZnLBr]ClO4 possessed a greater cytotoxic effect against the tested cells. © 2021 Elsevier B.V.
Publication Date: 2021
Journal of the Chinese Chemical Society (00094536)68(11)pp. 2140-2150
New complexes of 5-methyl-5-(4-nitrophenyl)-hydantoin (L) with HgX2 (X = Cl−, Br−, and I−) were synthesized and characterized by several means including Fourier-transform infrared (FT-IR), proton nuclear magnetic resonance (1H NMR), carbon nuclear magnetic resonance (13C NMR), mass, CHN, and Energy Dispersive X-ray analysis. The spectroscopic data verified the coordination of (L) to the Hg (II) metal centers from the oxygen atom of the carbonyl functional group. The resulting data show that the prepared complexes (1), (2), and (3) have a monodentate coordination mode to metal center and structures showing X-bridged dimers. The cytotoxicity of the prepared complexes was investigated against cancer cell lines including MCF-7 (breast), A549 (lung), and AGS (gastric) adenocarcinoma cells. The obtained data showed that complexes (1) and (2) represent a higher cytotoxic effect against the tested cells. Also, the antioxidant behavior study displayed notable antioxidant potencies for complexes (1) and (2) in comparison with ascorbic acid, as a standard. Also, for the theoretical study, density functional theory calculations at the BP86/def2-SVP level of theory were applied. The strength and nature of donor−acceptor bonds between (L) and Hg fragments in the system of [L → HgX2]2 were performed by the use of the natural bond orbital analysis, energy decomposition analysis, and their natural orbitals for chemical valence variation. © 2021 The Chemical Society Located in Taipei & Wiley-VCH GmbH.
Publication Date: 2020
Polyhedron (02775387)181
New Ni(II), Pd(II) and Pt(II) complexes of 5-methyl-5-(4-nitrophenyle)-hydantoin (L) were synthesized, characterized and their biological activities were evaluated. The resulting spectroscopic and theoretical data offered strong evidences for coordination of hydantoin based ligand from oxygen atom of C[dbnd]O group to the Ni(II), Pd(II) and Pt(II) metal centers. The theoretical data proposed cis and trans structures for complexes. Moreover, the cytotoxic activity of the compounds was tested against three different cancer cell lines including MCF-7 (breast), A549 (lung) and AGS (gastric) adenocarcinoma cells. Generally, Pt(II) complex possesses a higher cytotoxic effect against the tested cells than the Pd(II) complex. Likewise, antioxidant activity assay exhibited that both of the Pd(II) and Pt(II) complexes had significant potential compared to ascorbic acid and quercetin, as the standards. Also a theoretical study on structure of monomeric complexes of the form of [L → MCl2 ← L] where M = Ni(II), Pd(II) and Pt(II) have been investigated at the BP86/def2-SVP level of theory. The bonding situation between the [MCl2] and L fragments in [L → MCl2 ← L] complexes, were carried out by natural bond orbital (NBO) and energy-decomposition analysis (EDA), as well as its natural orbitals for chemical valence variation (EDA-NOCV). The results showed that the M ← O bond interaction energies (ΔEint) of the L and MCl2 fragments in metal complexes are substantial and conform to the V-shaped trend for the transition metals of the first, second, and third row as Ni > Pt > Pd. © 2020 Elsevier Ltd
Publication Date: 2020
Chemical Data Collections (24058300)26
By the reaction of 1-Fluoro-2-nitrobenzene with homopiperazine, the new polyamine 2,2′-(1,4 -diazepane -1,4-diyl)dianiline (A) was prepared. The N4O2 Schiff base ligands were synthesized from condensation of polyamine A with 2-hydroxybenzaldehyde (H2L1) or 2‑hydroxy-3-methoxybenzaldehyde (H2L2). Four macroacyclic Schiff-base complexes were obtained by reaction of cobalt (II) and copper (II) ions with ligands. All resulting compounds were characterized by 13C and 1H NMR, FT-IR, elemental analysis and mass spectrometry. Molar conductivity (ɅM) data were determined using 10−3 molar solutions of the synthesized compounds in acetonitrile. The antioxidant activity of all products has been studied. The geometries of the [MLn]m + (M = Co, Cu; Ln = L1, L2, L3, L4; m = 0, 1) complexes containing homopiperazine or piperazine moiety were optimized at the BP86/def2-SVP level of theory. Furthermore with the help of NBO and EDA, the nature of M ← Ln (n = 1 − 4) bonds in complexes are studied. © 2020
Publication Date: 2018
New Journal of Chemistry (11440546)42(17)pp. 14308-14317
Herein novel crab-like biological-based glycoluril with sulfonic acid tags, namely glycoluril tetrakis(butane-1-sulfonic acid) (GTBSA), was prepared in nano-size form and fully characterized via several techniques, such as 1H and 13C NMR, Fourier transform infrared spectroscopy (FT-IR), CHNS analysis, mass spectroscopy, X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal gravimetric analysis (DTG), scanning electron microscopy (SEM) and transmission electron microscopy (TEM). It is proved that this novel nanostructured catalyst is an efficient catalyst for the synthesis of novel spiropyrans via the one-pot multi-component condensation of isatine, naphthalene-2,3-diol or 2,5-dihydroxycyclohexa-2,5-diene-1,4-dione, and malononitrile or 1,3-dicarbonyl compounds in refluxing water. The mild reaction conditions, easy work-up, good to excellent yields and reusability of the catalyst are the major advantages of the described procedure. Results from DPPH radical scavenging assays showed that the synthesized compounds have eminent antioxidant efficacies (IC50:0.16 ± 0.01 to 0.55 ± 0.02 mg mL-1). Moreover, the in vitro antibacterial activities of the compounds were assessed against 4 Gram-positive and Gram-negative bacterial strains via a disc diffusion method. The results showed that compounds 2S and 3S possess high suitability for E. coli growth inhibition, comparable to the positive control gentamicin. © 2018 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Publication Date: 2018
Journal Of The Iranian Chemical Society (1735207X)15(2)pp. 471-481
Abstract: In this work, acetic acid functionalized poly(4-vinylpyridinum) bromide as a green and reusable catalyst was successfully tested on the synthesis of various bis-coumarins under solvent-free conditions. In addition, antioxidant and anti-inflammatory activities of the synthesized bis-coumarins were in vitro screened by 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging and formalin-induced edema model system, respectively. Antifungal activity was also evaluated against Fusarium oxysporum. Results showed that the synthesized bis-coumarins studied possess strong antioxidant (IC50; 0.149 ± 0.005 to 1.348 ± 0.006 mg/ml) and anti-inflammatory activities in comparison with ascorbic acid and diclofenac as positive controls, respectively. Also, the compounds showed good inhibition activity against Fusarium oxysporum (58 ± 1.4 to 100 ± 0.0%). For their biological activities, the synthesized bis-coumarins may be suggested to apply as biological agents for special use in future. Graphical Abstract: [Figure not available: see fulltext.] © 2017, Iranian Chemical Society.
