New asymmetric Schiff base ligand derived from allylamine and 2,3-dihydroxybenzaldehyde and its molybdenum(VI) complex: Synthesis, characterization, crystal structures, computational studies and antibacterial activity together with synergistic effect against Pseudomonas aeroginosa PTTC 1570

Rudbari, Hadi Amiri; Khorshidifard, Mahsa; Askari, Banafshe; Habibi, Neda; Brunò, Giuseppe

doi:10.1016/j.poly.2015.07.060

Cited by 31 publications

(9 citation statements)

References 80 publications

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“…Holm and co-workers have demonstrated that a similar isomer of (Et 4 N) 2 [WO 3 (Cl 2 bdt)] also exhibited a difference between the W–S Cl2bdt bonds as a result of a trans influence, although the difference was significantly smaller (∼0.1 Å) . Significantly larger Mo–O catecholate bond length differences of up to 0.25 Å were reported in octahedral [MoO 2 (catecholate) 2 ] 2– , where only one of the two catecholate oxygens was trans to oxo. − The catecholate is rotated away from the Cu center about the C imine –C catecholate bond. All optimized isomers demonstrated similar coordination environments for the Cu(I)/Mo(VI) ions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Cu(I)/Mo(VI) Reactivity of a Bifunctional Heterodinucleating Ligand on a Xanthene Platform

et al. 2021

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In an effort to probe the feasibility of a model of Mo-Cu CODH (CODH = carbon monoxide dehydrogenase) lacking a bridging sulfido group, the new heterodinucleating ligand LH 2 was designed and its Cu(I)/Mo(VI) reactivity was investigated. LH 2 ((E)-3-(((5-(bis(pyridin-2-ylmethyl)amino)-2,7-di-tert-butyl-9,9-dimethyl-9H-xanthen-4-yl)imino)methyl)benzene-1,2-diol) features two different chelating positions bridged by a xanthene linker: bis(pyridyl)amine for Cu(I) and catecholate for Mo(VI). LH 2 was synthesized via the initial protection of one of the amine positions, followed by two consecutive alkylations of the second position, deprotection, and condensation to attach the catechol functionality. LH 2 was found to exhibit dynamic cooperativity between two reactive sites mediated by H-bonding of the catechol protons. In the free ligand, catechol protons exhibit H-bonding with imine (intramolecular) and with pyridine (intermolecular in the solid state). The reaction of LH 2 with [Cu-(NCMe) 4 ] + led to the tetradentate coordination of Cu(I) via all nitrogen donors of the ligand, including the imine. Cu(I) complexes were characterized by multinuclear NMR spectroscopy, high-resolution mass spectrometry (HRMS), X-ray crystallography, and DFT calculations. Cu(I) coordination to the imine disrupted H-bonding and caused rotation away from the catechol arm. The reaction of the Cu(I) complex [Cu(LH 2 )] + with a variety of monodentate ligands X (PPh 3 , Cl − , SCN − , CN − ) released the metal from coordination to the imine, thereby restoring imine H-bonding with the catechol proton. The second catechol proton engages in H-bonding with Cu−X (X = Cl, CN, SCN), which can be intermolecular (XRD) or intramolecular (DFT). The reaction of LH 2 with molybdate [MoO 4 ] 2− led to incorporation of [Mo VI O 3 ] at the catecholate position, producing [MoO 3 (L)] 2− . Similarly, the reaction of [Cu(LH 2 )] + with [MoO 4 ] 2− formed the heterodinuclear complex [CuMoO 3 (L)] − . Both complexes were characterized by multinuclear NMR, UV−vis, and HRMS. HRMS in both cases confirmed the constitution of the complexes, containing molecular ions with the expected isotopic distribution.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Cu(I)/Mo(VI) Reactivity of a Bifunctional Heterodinucleating Ligand on a Xanthene Platform

et al. 2021

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“…The intramolecular H-bond distances and angle are also in the expected range (N-H: 0.88 Å, H … O: 1.88 Å, N … O: 2.5673(4) Å and NHO: 134 ). [78,79]…”

Section: X-ray Crystal Structure Of [Ag (Br 2 -L 2 )No 3 ] M (Ag6)mentioning

confidence: 99%

Antimicrobial and antiprotozoal activities of silver coordination polymers derived from the asymmetric halogenated Schiff base ligands

Kordestani

Rudbari

Fateminia

et al. 2020

Applied Organom Chemis

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A series of polymeric silver(I) complexes with Schiff base ligands containing pyridine and 3,5‐halogen substituted phenol moieties were synthesized and characterized by spectroscopic methods and in the case of Ag6 also by X‐ray crystallography. All silver(I) complexes (Ag1–Ag8) were evaluated for their biological activity against a panel of pathogens including the protozoa Trypanosoma cruzi, T. brucei, T. rhodesiense and Leishmania infantum; the bacteria Staphylococcus aureus, Escherichia coli, Mycobacterium tuberculosis H37Ra and the yeast Candida albicans. Cytotoxicity evaluation was carried out on human lung fibroblasts (MRC‐5) and on primary peritoneal mouse macrophages. The most relevant result reveals antileishmanial activity potential with all complexes demonstrating higher potency than the reference drug miltefosine. Complexes with the best antiprotozoal profile (i.e., Ag2 and Ag7) were selected for incorporation into poly (lactic acid) nanoparticles (PLA NPs) with the aim to enhance selectivity. PLA/Ag2 NPs and PLA/Ag7 NPs exhibited adequate physicochemical properties, that is, average size of 263 ± 60 nm and 225 ± 6 nm, respectively, good entrapment efficiency (69% and 63%), loading content (6.2% and 5.7%) and stability. The cytotoxicity of PLA/Ag2 NPs and PLA/Ag7 NPs on MRC‐5 cells was reduced with respect to the “free” metal complexes by ~2‐fold and ~6‐fold, respectively.

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“…In recent years, Schiff base metal complexes have taken wide attention due to broad applications such as anticancer, antioxidant, antifungal and anticonvulsant-centigrade, corrosion inhibition and also anti-inflammatory activity [1][2][3]. The azomethine functional group (C=N) has extraordinary donor properties and is vital for coordination chemistry.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural studies and antioxidant activities of M(II) complexes with NOS donor schiff base ligand

Turan¹

2021

Sigma J Eng Nat Sci - Sigma Müh Fen Bil Derg

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Schiff base ligand, (E)-methyl 6-acetamido-2-(5-bromo-2-hydroxybenzylideneamino)-4,5,6,7tetrahydrobenzo[b]thiophene-3-carboxylate, was successfully prepared with condensation reaction. The newly obtained Schiff base used to synthesize five new complex, [FeLCl(From the magnetic and spectral data, the geometric structures of these complexes were found to be square planar and octahedral. The characterizations of ligand and complexes were done by FT-IR, UV-Vis, 1 H and 13 C-NMR, microanalyses, magnetic susceptibility, mass spectra and thermogravimetry analysis (TGA) and further were screened for antioxidant activities. Antioxidant properties of synthesized compounds were examined using different methods including total antioxidant activity, FRAP (ferric reducing antioxidant power), CUPRAC (cupric reducing antioxidant capacity) and DPPH (2,2-diphenyl-1-picrylhydrazyl). The Ru(II), Pd(II), Fe(II) and Co(II) metal complexes generally exhibited good antioxidant properties.

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New asymmetric Schiff base ligand derived from allylamine and 2,3-dihydroxybenzaldehyde and its molybdenum(VI) complex: Synthesis, characterization, crystal structures, computational studies and antibacterial activity together with synergistic effect against Pseudomonas aeroginosa PTTC 1570

Cited by 31 publications

References 80 publications

Synthesis and Cu(I)/Mo(VI) Reactivity of a Bifunctional Heterodinucleating Ligand on a Xanthene Platform

Synthesis and Cu(I)/Mo(VI) Reactivity of a Bifunctional Heterodinucleating Ligand on a Xanthene Platform

Antimicrobial and antiprotozoal activities of silver coordination polymers derived from the asymmetric halogenated Schiff base ligands

Synthesis, structural studies and antioxidant activities of M(II) complexes with NOS donor schiff base ligand

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