Synthesis and Investigation of Antimicrobial, Antioxidant, Enzymatic Inhibitory, and Antiproliferative Activities of Ruthenium (II) Complexes Bearing Benzimidazole-Based N-Heterocyclic Carbene (NHC) Ligands (original) (raw)
Related papers
Inorganica Chimica Acta, 2017
In search of a new antimicrobial and antioxidant with improved potency, we designed and synthesized a pair of chromone hydrazones and their transition metal complexes. The characterization and elucidation of the structure of the prepared compounds were performed by elemental analysis, IR, electronic, EPR and thermo gravimetric analyzes, as well as conductivity and magnetic susceptibility measurements. The EPR spin Hamiltonian parameters of copper complexes were calculated. The spectroscopic data showed that the ligands act as a monobasic tridentate. The coordination sites with the metal (II) ion are pyrone oxygen, azomethine nitrogen and hydrazonic oxygen. Hydrazones and their metal complexes have shown antimicrobial activity against Gram-positive bacteria (S. aureus and B. subtilis); Gram-negative bacteria (P. aeruginosa and E. coli) and fungus (C. albicans) and also the synthesized ligands were tested for their antioxidant activity in vitro by DPPH scanning and the ABTS radical method. The substitution requirements for favorable antioxidant activity were investigated. Compounds containing a phenolic hydroxyl group at the imine (azomethine) position as well as an additional electron donor group exhibited lower IC 50 values and the result shows that all hydrazones have a significant antioxidant activity compared to the standard antioxidants Trolox.
Synthesis and antioxidant activity evaluation of a syringic hydrazones family
European journal of medicinal chemistry, 2010
A novel series of hydrazones derived from syringaldehyde and their antioxidant properties have been explored. Several employed methods such as scavenging effect on 2,2diphenyl-1-picrylhydrazyl (DPPH) radical and 2,2,′-azinobis(3-ethylbenzthiazoline-6-sulfonic acid (ABTS •+) radical cation expressed as Trolox equivalent antioxidant capacity (TEAC), inhibition of superoxide anion (O 2 -) generation and of human cell-mediated low-density lipoprotein oxidation (monitored by the formation of TBARS) exhibited their potent antioxidant properties. The carbonyl scavenger efficacy was also evaluated by measuring the ability to decrease the protein carbonyl content in cells challenged with oxidized LDL. In this report, we discuss about the synthesis of hydrazones and their dual biological role, antioxidant and carbonyl scavenger for further application in atherosclerosis.
A series of 20 metal based [Cu(II), Co(II), Ni(II), Mn(II) and Zn(II)] compounds have been synthesized with novel 2,5dihydroxyacetophenone isonicotinoyl hydrazone (L 1) and 2,5-dihydroxyacetophenone benzoyl hydrazone (L 2) Schiff bases and were screened for antioxidant and cytotoxic activities. All these complexes exhibited strong antioxidant activity against DPPH radical but no nitric oxide radical scavenging activity. Cytotoxicity assay showed toxicity at varied levels, that is,
Journal of Applied Pharmaceutical Science
In the present study, a series of 4-hydroxy-Nʹ-[(1E)-substituted-phenylmethylidene] benzohydrazide analogs was synthesized, characterized, and evaluated for their antibacterial and anti-oxidant activity. All the tested compounds show high antibacterial activity with compound AR 7 , Nʹ-(3,4,5-trimethoxybenzylidene)-4-hydroxybenzohydrazide as the most active compound, whereas compounds AR 10 (hydrogen peroxide scavenging) and AR 8 (2,2-diphenyl-1picrylhydrazyl radical scavenging activity method) were found to possess maximum anti-oxidant activity indicating that different mechanisms are involved in different anti-oxidant determination methods.
Synthesis, in vitro safety and antioxidant activity of new pyrrole hydrazones
Acta Pharmaceutica, 2020
, in vitro safety and antioxidant activity of new pyrrole hydrazones Six new N-pyrrolylhydrazide hydrazones were synthesized under micro synthesis conditions, assuring about 59-93 % yield, low harmful emissions and reagent economy. The structures of the new compounds were elucidated by melting points, TLC characteristics, IR, 1 H and 13 C NMR spectral data followed by MS data. The purity of the obtained compounds was proven by the corresponding elemental analyses. "Lipinski's rule of five" parameters were applied for preliminary evaluation of the pharmacokinetic properties of the target molecules. The initial in vitro safety screening for cytotoxicity (on HepG2 cells) and hemocompatibility (hemolysis assay) showed good safety of the new compounds, where ethyl 5-(4-bromophenyl)-1-(1-(2-(4-hydroxy-3-methoxybenzylidene)hydrazineyl)-1-oxo-3-phenylpropan-2-yl)-2-methyl-1H-pyrrole-3-carboxylate (4d) and ethyl 5-(4-bromophenyl)-1-(1-(2-(2hydroxybenzylidene)hydrazineyl)-1-oxo-3-phenylpropan-2-yl)-2-methyl-1H-pyrrole-3-carboxylate (4a) were the least toxic. The antioxidant activity in terms of radical scavenging activity (DPPH test) and reducing ability (ABTS) was also evaluated. The antioxidant protective potential of the compounds was next determined in different in vitro cellular-based models, revealing compounds 4d and 3 [ethyl 5-(4-bromophenyl)-1-(1-hydrazineyl-1-oxo-3-phenylpropan-2-yl)-2-methyl-1H-pyrrole-3-carboxylate] as the most promising compounds, with 4d having better safety profile.
Synthesis, in vitro safety and antioxidant activity of new pyrrole hydrazones
Acta Pharmaceutica
Six new N-pyrrolylhydrazide hydrazones were synthesized under micro synthesis conditions, assuring about 59–93 % yield, low harmful emissions and reagent economy. The structures of the new compounds were elucidated by melting points, TLC characteristics, IR, 1H and 13C NMR spectral data followed by MS data. The purity of the obtained compounds was proven by the corresponding elemental analyses. “Lipinski’s rule of five” parameters were applied for preliminary evaluation of the pharmacokinetic properties of the target molecules. The initial in vitro safety screening for cytotoxicity (on HepG2 cells) and hemocompatibility (hemolysis assay) showed good safety of the new compounds, where ethyl 5-(4-bromophenyl)-1-(1-(2-(4-hydroxy-3-methoxybenzylidene)-hydrazineyl)-1-oxo-3-phenylpropan-2-yl)-2-methyl-1H-pyr-role-3-carboxylate (4d) and ethyl 5-(4-bromophenyl)-1-(1-(2-(2-hydroxybenzylidene)hydrazineyl)-1-oxo-3-phenylpropan--2-yl)-2-methyl-1H-pyrrole-3-carboxylate (4a) were the least toxic....
Jundishapur Journal of Microbiology
Background: The semi-synthesis of drugs from natural products is still limited and complicated. Recently, there has been compelling global need to develop novel and potential antibacterial and antioxidant agents. Objectives: The current study aimed at semi-synthesizing new derivatives from naringin, to verify their chemical structures and assess their antibacterial and antioxidant potentials. Methods: The semi-synthesis of naringin was conducted in the presence of hydrazone and oxime derivatives in acidic solution, while elemental and spectral analytical methods were used to verify the chemical structures of the semi-synthesized molecules. Also, to assess their antibacterial activity, the micro-broth dilution method with different American type culture collection (ATCC) strains as Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, and clinical isolate methicillin-resistant Staphylococcus aureus (MRSA) were utilized. Moreover, 2, 2-Diphenyl-1-Picrylhydrazyl (DPPH) was used to assess the antioxidant activity of the derived compounds. Results: Three new hydrazone and oxime compounds were semi-synthesized from naringin and their chemical structures were identified by 13 C NMR, IR, MS, and 1 H NMR. Among the semi-synthesized compounds, the (2a) molecule showed the best antibacterial activity with a minimum inhibitory concentration (MIC) value of 62.5 µg/mL. Also, this compound exhibited the best antioxidant activity with IC50 3.7 µg/mL, in comparison with the other studied samples. Conclusions: Hydrazone (2a) compound could be used as a potent antioxidant and bacterial agent. Further studies are required to investigate other therapeutic effects of the (2a) molecule.
Heliyon, 2020
There has been substantial interest over the past many years in the design of novel chemical compounds containing the azomethine group (-NH-N¼CH) and exhibiting various medicinal properties such as antibacterial, antiviral, antifungal, and anti-inflammatory activities. Herein, hydrazones were synthesized via the chemical reaction of substituted aromatic hydrazides with various aromatic aldehydes. The obtained products were confirmed using different physical and spectroscopic techniques, such as m.p., IR, 1 H-NMR and 13 C-NMR. The present study was designed to synthesize different aromatic hydrazones assembled by various combinations of aromatic hydrazides and aromatic benzaldehydes containing different substituents such as hydroxyl and polyhydroxyl groups as key structural features. Thus, incorporating such moieties and simultaneously creating highlyconjugated systems was expected to create novel species to mimic as much as possible natural phenolics, chalcones and stilbenes. Compounds of aromatic hydrazones synthesized in the present study were tested in vitro for their direct and indirect antioxidant activities using different methods such as DPPH, ABTS and FTC. The antioxidant activities of the new compounds ranged from very weak to very high activity. In addition, the inhibition of tyrosinase and cholinesterase by these compounds was tested. The new compounds containing two or three hydroxyl groups attached to aldehyde rings exhibited significantly greater inhibition effects on tyrosinase or cholinesterase activities in comparison to other compounds of the same series containing only one hydroxyl group.
Social Science Research Network, 2021
New photophysical and antioxidant materials of trimesic trihydrazide derivatives were synthesized by one-pot stage of trimesic trihydrazide and different aromatic aldehydes. All compounds were characterized by spectroscopic techniques (NMR, MS, and IR) and elemental analysis. The absorption and emission spectral characteristics of hydrazone derivatives were investigated. The absorption maxima showed red shift relative to the starting compound. While the emission maxima showed clear dependent on the type of substituents. The electron donating and electron withdrawing showed red and blue shifts relative to the starting compound, respectively. The compounds' effectiveness as antioxidant was estimated by DPPH radical scavenging and ABTS radical cation assays in vitro which indicated that the derivatives could be used as potential antioxidants. In addition, compounds 3g, and 3i showed strong antioxidant activities according to the DPPH assay and compounds 3c and 3m exhibited good antioxidant activities in ABTS assay. Antimicrobial activity of the derivatives was estimated using a micro-broth dilution method. Furthermore, molecular geometries of all prepared derivatives were fully optimized using density functional theory (DFT) calculations at the 6-31G(d)/B3LYP level of theory.
Organic Communications
In this research, five novel hydrazone derivatives (2a-e) were obtained for the first time, characterized and investigated for their antioxidant properties, and acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. The target molecules were easily synthesized by the condensation reaction of 2,4dinitrophenylhydrazine (2,4-DNPH) with aryl esters (1a-e) derived from salicylaldehyde as a starting material. These molecules were fully elucidated by some spectroscopic techniques and elemental analysis. Antioxidant activities of newly synthesized molecules were examined by CUPRAC reducing, ABTS and DPPH radical scavenging assays. The IC50 values of the screened molecules were determined in the range of 72.54-221.52 µM against AChE and in the range of 8.46-48.28 µM against BChE. Among the tested molecules, compound 2e indicated the highest activity against both AChE and BChE. Also, the inhibitory capacities of all tested molecules were compared to the standard molecules galanthamine. On the other hand, In CUPRAC reducing assay, the target molecules exhibited antioxidant activities in the range of 30.29 and 59.43 µM. Among these compounds, compound 2b (IC50=30.29 µM) showed the closest activity to the standard compounds butylated hydroxytoluene (BHT) (IC50=30.62 µM) and butylated hydroxyanisole (BHA) (IC50=34.24 µM).