Synthesis, characterization and biological activity of novel complexes of zinc(II) diclofenac with nitrogen based ligands

2018

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Novel Zn(II) complexes with the general formula: [Zn(furo) 2 (L) n ], n = 1 or 2, (furo = furosemide = (4-chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoic acid) were prepared. The complexes [Zn(furo) 2 (MeOH) 2 ] (1; MeOH = methanol), [Zn(furo) 2 (2-ampy) 2 ] (2; 2-ampy = 2-aminopyridine), [Zn(furo) 2 (2-ammepy) 2 ] (3; 2-ammepy = 2-aminomethylpyridine), [Zn(furo) 2 (H 2 O)(2,2-bipy)] (4; 2,2′bipy = 2,2′-bipyridine), [Zn(furo) 2 (H 2 O)(4,4′-bipy)] (5; 4,4′-bipy = 4,4′bipyridine), [Zn(furo) 2 (1,10-phen)] (6; 1,10-phen = 1,10-phenanthroline),[Zn(furo) 2 (2,9-dmp)] (7; 2,9-dmp = 2,9-dimethyl-1,10-phenanthroline), and [Zn (furo) 2 (quin) 2 ] (8; quin = quinoline) were synthesized and characterized using different techniques such as IR, UV-Vis, 1 H NMR, 13 C NMR, LC/MS and others. The crystal structure of complex (4) was determined using singlecrystal X-ray diffraction.The anti-bacterial activity of complexes (1-8) was tested using agar diffusion method against three gram-positive (Staphylococcus aureus, Bacillus subtilis and Staphylococcus epidermidis) and three gram-negative bacteria (Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa). The obtained results showed different Inhibition Zone Diameters (IZD) with various anti-bacterial activities against the selected gram-positive and gram-negative bacteria. In addition, the rate of bis-(4-nitrophenyl) phosphate hydrolysis was measured at different temperatures, different pH values and different concentrations. The rates for the eight complexes were in the following order: complex 4 > 2 > 5 > 8 > 7 > 6 > 3 > 1. KEYWORDS anti-bacterial activity, bioactive nitrogen based ligands, bis-(4-nitrophenyl) phosphate, furosemide, zinc(II) complexes

Section: Resultssupporting

confidence: 62%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Structures and Various Biological Applications of New Zn(II) Complexes Having Different Coordination Modes Controlled by the Drug Furosemide in Presence of Bioactive Nitrogen Based Ligands

Raymoni

2018

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“…Hydrogen bonding between molecules plays a key role in the complex geometry and in stabilizing the complex in the solid state. [ 102,103 ] The nitrate ion and lattice water molecules are involved in a series of strong and highly directional O–H···N and O–H···O bonding interactions.…”

Section: Resultsmentioning

confidence: 99%

Two novel Cu (II) levofloxacin complexes with different bioactive nitrogen‐based ligands; single‐crystal X‐ray and various biological activities determinations

Mubarak

Metani

2021

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Two new copper (II) complexes with the third generation quinolone antibacterial agent levofloxacin, 2‐aminopyridine and 2,2′‐bipyridine nitrogen‐based ligands with the following molecular structures [Cu (levo)2(2‐ampy)].6.25H2O (1) and [Cu (levo)(H2O)(2,2‐bipy)](NO3).2.5H2O (2) were synthesized. The complexes were characterized by spectroscopic methods and others. The crystal structure of complex 1 revealed that the Cu (II) cation is coordinated to two bidentate chelating levofloxacinato ligands, and one monodentate 2‐ampy ligand in the axial position forming a slightly distorted square pyramidal geometry. The mononuclear cationic complex 2 was determined in the triclinic crystal system and the chiral space group P1 with four molecules per unit cell in which the Cu (II) cation is coordinated to one bidentate chelating levofloxacinato ligand, one bidentate 2,2‐bipy, and one water molecule in a distorted square pyramidal geometry. In vitro antibacterial activities for the complexes and their parent ligands against four gram‐negative bacteria (Proteus mirabilis, Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumonia) and four gram‐positive bacteria (Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, and Enterococcus faecalis) using the agar diffusion method have been determined with inhibition zone diameter (IZD) values between 29 and 46 mm. In addition, the minimum inhibition concentration (MIC) and the minimum bactericidal concentration (MBC) have been investigated. The MIC results of complexes 1 and 2 showed significant antibacterial activities against the P. mirabilis and B. subtilis than levofloxacin.

Synthesis, characterization and in vitro biological activity of new zinc(II) complexes of the nonsteroidal anti‐inflammatory drug sulindac and nitrogen‐donor ligands

Shalash

Akkawi

et al. 2017

Metal carboxylate compounds with nitrogen‐ and/or oxygen‐donor ligands with various carboxylate coordination modes, monodentate, bidentate and bridging bidentate, have been shown to be important from biological and chemical aspects. Five zinc ion binary compounds, diaqua‐bis‐(2‐((E)‐5‐fluoro‐2‐methyl‐1‐(4‐(methylsulfinyl)benzylidene)‐1H–inden‐3‐yl)acetato)zinc(II) (1), aqua‐bis‐(2‐((E)‐5‐fluoro‐2‐methyl‐1‐(4‐(methylsulfinyl)benzylidene)‐1H–inden‐3‐yl)acetato)pyridin‐2‐aminezinc(II) (2), (2‐((E)‐5‐fluoro‐2‐methyl‐1‐(4‐(methylsulfinyl)benzylidene)‐1H–inden‐3‐yl)acetato) pyridin‐2‐ylmethanaminezinc(II) (2‐((E)‐5‐fluoro‐2‐methyl‐1‐(4‐(methylsulfinyl)benzylidene)‐1H–inden‐3‐yl)acetate) (3), bis‐(2‐((E)‐5‐fluoro‐2‐methyl‐1‐(4‐(methylsulfinyl)benzylidene)‐1H–inden‐3‐yl)acetato)‐1,10‐phenanthrolinezinc(II) (4) and bis‐(2‐((E)‐5‐fluoro‐2‐methyl‐1‐(4‐(methylsulfinyl)benzylidene)‐1H–inden‐3‐yl)acetato)‐1,10‐phenanthrolinezinc(II) (5), have been prepared and fully characterized. In addition, the complexes were evaluated for their antibacterial activity using the in vitro agar diffusion method against two Gram‐positive (Staphylococcus epidermidis, Staphylococcus aureus) and two Gram‐negative (Bordetella, Escherichia coli) bacteria and yeast species (Saccharomyces and Candida). Complex 5 showed reasonable activity against yeast. All compounds showed greater antibacterial activity against Gram‐positive than Gram‐negative bacteria. Results indicated that the efficiency of complex 5 in preventing the formation of β‐hematin was 67.6%. The efficiency of chloroquine as a standard drug was reported as 93%. Furthermore, the phosphatase activity of the Zn(II) complexes was studied and results indicated an effect of the zinc complexes on phosphatase activity.