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Synthesis, structural determination and antibacterial activity of compounds derived from vanillin and 4-aminoantipyrine


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Schiff bases derived from 4-aminoantipyrine and vanillin were evaluated for their potential as antibacterial agents against some Gram positive and Gram negative bacterial strains. The antibacterial activity was studied against P. pseudoalcaligenes ATCC 17440, P. vulgaris NCTC 8313, C. freundii ATCC 10787, E. aerogenes ATCC 13048, S. subfava NCIM 2178 and B. megaterium ATCC 9885. The determination of the antibacterial activity was done using the Agar Ditsh method. The Schiff bases produced were: (1) 4-(4-hydroxy-3-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one [VV1]; (2) 4-(benzylideneamino)-1,5-dimethyl-2-phenyl-1,2-dihydro- pyrazol-3-one [VY2]); (3) 4-[(furan-3-ylmethylene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one [VY3]; (4) 4-(4-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl- 1,2-dihydro-pyrazol-3-one [VY4]; (5) 2-methoxy-4-[(4-methoxyphenylimino)methyl]phenol [VY5]; (6) 4-[(2,4-dimethylphenylimino)methyl]-2-methoxyphenol [VY6]); (7) 2-methoxy-4-(naphthalene-1-yliminomethyl)phenol [VY7] and (8) 4-[(4-hydroxy-3-methoxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamide [VY8]. The antibacterial activity was evaluated in two polar solvents, DMSO and DMF. The Schiff bases derived from vanillin as the central molecule with 2,4-dimethylaniline and sulphamethoxazole as the side chain in DMSO effectively inhibited the investigated bacteria and appear to be promising antimicrobial agents.
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... The increased lipophilicities of Schiff bases and complexes permit easy penetration into lipid membranes and seizing the growth of the organism (Abu-Dief & Mohamed, 2015). Metal complexes also disturb the respiration process of the cell and thus block the synthesis of proteins, which restricts further growth of the organisms (Vaghasiya et al., 2004;Gudasi et al., 2005). ...
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The present study aims to evaluate the antibacterial activity of some Schiff base chelates, where the Schiff bases were obtained by condensation process of 2-hydroxyacetophenone with tyrosine as the main ligand (HL1) and 4-dimethylaminobenzaldehyde with 2-aminobenzoic acid as a secondary ligand (HL2) against five pathogenic bacteria species, like Staphylococcus aureus and Enterococcus faecalis, Pseudomonas aeruginosa, Klebsiella sp. and Escherichia coli using the agar well diffusion assay. Schiff base HL1 exhibited the highest antibacterial activity than Schiff base HL2 against all the bacterial species. The chelates, Ni(II) and Zn(II) ions showed a good inhibitory effect against all the tested bacterial species, while, the other chelates Co(II), Cu(II) and Fe(III) ions did not reveal any effect on all tested bacteria. Schiff base HL1, Ni(II) and Zn(II) chelates were the most effective compounds that showed bacteriostatic and bactericidal activities against all the tested pathogenic bacteria species with MIC ranged from 3.1 to 25 mg/ml and MBC from 6.2 to 50 mg/ml.
... 4-Aminoantipyrine is known for the variety of its clinical applications such as anti-inflammatory, analgesic, antipyretic [25,26], and several chemotherapeutic agents [27]. It is evident from the reported literatures that compounds possessing pyrazole nuclei showed significant anthelmintic as well as antimicrobial activities [28][29][30]. The life of mechanical hardware is established by good corrosion control. ...
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The control of mild steel corrosion is of technical, economic, environmental and aesthetic importance. One of the best options is to use inhibitors to protect mild steel from corrosion. Some organic corrosion inhibitors are toxic to the environment, as they are degradable but have the advantage of not containing heavy metals. The toxicity of some organic inhibitors has led to a search for green corrosion inhibitors or non-toxic organic compounds that may be derived from a natural product. Plant products are inexpensive, readily available, and renewable, in addition to being environmentally friendly and acceptable. Investigations into the corrosion inhibition capabilities of 4-aminoantipyrine and its derivatives are of interest as it is the basis for the manufacture of many drugs and pharmaceutical products. Recently, scientists have started using 4-aminoantipyrine as a promising inhibitor. Reports regarding the mechanisms of the 4-aminoantipyrine adsorption process and the mechanism of corrosion inhibition are still unclear, although substantial research has been devoted to preventing corrosion by 4-aminoantipyrine. The development of computational modeling which supported by experimental results will help fill this void and help to understand the mechanism of action of 4-aminoantipyrine absorption patterns on the mild steel surface. Thus, the use of theoretical studies will help to develop excellent corrosion inhibitors with an understanding of the mechanisms of inhibition. The present review article limits the use of 4-aminoantipyrine derivatives as anti-corrosive agents.
... The samples were examined for antibacterial activity against Klebsiella pneumoniae, Pseudomonas aeruginosa and Stapylococcus aureus. Antifungal study was carried out against Aspergillus flavus, Rhizopus microspores and Candida albicans (Yogeshi et al., 2004;Perez et al., 1990). ...
In this work, a Cu coating on carbon steel with a fine crevice structure created by laser modification was produced without the use of contaminants by exploiting the super-spread wetting properties of liquid metal. The chemical composition, microstructure, bonding properties, corrosion resistance, and antibacterial activity of the Cu coating were investigated. The coating consisted of metallic Cu containing a minor fraction of Cu2O, with surface flakes and a dense inner layer with 0.1 % porosity and thickness of 337 ± 10 μm. Three-point bending tests showed the Cu coating had good adhesion with the carbon steel substrate. Corrosion tests demonstrated that the dense structure of the Cu coating blocked electrolyte contact with the carbon steel substrate for at least 336 h, indicating that the coating provides a barrier against galvanic corrosion. Assays of antibacterial activity and biofilm inhibition suggested that growth of Escherichia coli and Staphylococcus epidermidis on the Cu coating was 99.9 % lower than that on the substrate after 2 h surface contact, and biofilm formation on the coating was >90 % lower than that on the substrate. The combined anti-corrosive properties and antibacterial activity demonstrate the potential for the Cu coating to prevent transmission of bacterial infections in hospitals and public environments.
In this study, the usability of inorganic and organic compounds containing imine bonds as thermal stabilizers in rigid PVC production at 190 °C were investigated. In the results of thermogravimetric analysis, it was observed that the thermal stability of inorganic compounds increased compared to organic compounds. As a result of mixing the synthesized inorganic and organic compounds with the base stabilizer at different rates, the plasticization torque and time and thermal endurance times were compared with the reference stabilizer used in the market. Due to the high thermal stability of the compounds, it is thought that it can be preferred because it degrades in a longer time than the reference thermal stabilizer used in the industry.
Synthesis of some ternary complexes with isatin (ISA) as primary ligand and N,N,N,N‐tetramethyl ethylene diamine (TMEDA) as secondary ligand with a series of metal ions (M) Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) is presented. IR, elemental analysis, melting point, molar conductance, mass and thermal analysis were applied to characterize the prepared compounds. Conductometry measurements reveal that all complexes are non‐electrolytes except Cr(III), Mn(II), Fe(III) and Co(II) complexes. In the light of magnetic and solid reflectance techniques, all prepared complexes were suggested in an octahedral geometry. ESR study of Cu(II) complex prove its octahedral geometry. The mixed ligand complexes were found to have the formulae [M(ISA)(TMEDA)Cl2] where M=Ni(II), Cu(II) and Zn(II); [M(ISA)(TMEDA)Cl2]Cln.xH2O in case of M=Cr(III), Fe(III) and Cd(II) (where n=l, x=0 for Cr(III), n=l, x=0 for Fe(III) and n=0, x=2 for Cd(II) and [M(ISA)(TMEDA)Cl(H2O)]Cl in case of M=Mn(II) and Co(II). Antimicrobial activity of some complexes are higher than parent ligands. Molecular docking study confirmed the importance of Cu(II), Ni(II) and Cr(III) complexes as they have the highest interaction with the receptors of crystal structure of S.aureus nucleoside (PDB ID: 3Q8U), E. coli (PDB: 3T88) and protein phosphatase (PPZl) of C. albicans (PDB: 5JPE) with minimum binding energy of −2l.5, −7.2 and −45.6 kcal/mol, respectively. Synthesis and spectral identification of some ternary complexes with isatin (ISA) and (TMEDA) ligands have been studied using elemental analysis, IR, conductivity measurement, mass, UV‐Vis spectral, magnetic susceptibility, diffused reflectance spectral and thermal analysis. ESR of Cu(II) complex support the suggested chemical structure as octahedral geometry. Antimicrobial behaviors and molecular docking have been also run for the compounds. The findings prove the antibacterial and antifungal activity of the prepared compounds.
Vanillin (4-hydroxy-3-methoxybenzaldehyde) is a known natural aromatic flavoring agent and the major component of vanilla extracted from cured vanilla pods. Vanillin has several applications in foods, beverages, pharmaceuticals, perfumes and cosmetics. The Food and Drug Administration (FDA) and Flavor and Extract Manufacturers Association (FEMA) have recommended vanillin as safe and pose minimum detrimental consequences. Additionally, several studies have reported the pharmacological activities of vanillin including anticancer, antidiabetic, antioxidant, antisickling, antimicrobial, anti-inflammatory, aphrodisiac, cardio-protective, diuretic, amongst others. In spite of these interesting reports, the general perception of vanillin has been restricted to its role as a food additive. Therefore, we reviewed the pharmacological activities of vanillin to demonstrate its therapeutic potentials, especially as a component of functional foods. We further highlighted the biosynthesis, toxicity, bioavailability and other applications of the compound. Our review revealed that vanillin holds promising potentials in the prevention and cure of diverse human (metabolic and non-metabolic) diseases and is relatively bioavailable in the systemic circulation that could warrant a clinical trial.
Current research targets innovative medical textiles of nanofibrous nature and antibacterial activity to prevent diaper dermatitis. The work is based on electrospun nanofibers from cellulose acetate (CA) and lignin (Lig) polymers. A series of new copper complexes were synthesized and loaded to the CA/Lig solution mix then subjected to electrospinning, giving rise to the tricomponent bioactive mats CA/Lig/Cu-complex. The surface morphology of electrospun nanofiber mats was smooth and homogenous as the concentration of lignin increased in the mixture. The incorporation of lignin improved the electrospinnability of the cellulose acetate; however, it increased the fiber diameter. The water contact angle, absorption underload were significantly improved as lignin content increased. The incorporation of Cu-complex in electrospun CA and CA/Lig fiber mats occurred without any substantial change in the surface morphology, indicating well encapsulation of the complex. The electrospun mats were active against Pseudomonas aeruginosa, Acinetobacter baumannii, Staphylococcus epidermidis, and Streptococcus faecalis. The cytotoxicity, protein leakage, and biological results, together with the above studies, would advocate copper complex loaded CA/Lig fibers as a potential candidate for hygienic applications.
6-amino-2-(4-nitrophenyl)-1H-benzimidazole (6A2NHB) was synthesized and characterized by FT-IR, UV visible spectroscopy. The optimized structure, geometry parameters and wavenumbers of the title compound were calculated using the basis sets of Hartree Fock and DFT (B3LYP/ B3PW91) methods with 6-311 G (d, p) and 6-311++ G (d, p) and analyzed with experimental data. Electronic absorption spectra and ¹H-¹³C NMR studies have been computed in gas and solvents (DMSO, chloroform, water) by using TD-DFT (IEF-PCM). To know the stability, hyper conjugative interaction and delocalization NBO study has been executed. Molecular electrostatic potential reveals the chemical reactivity sites for the reaction. Antimicrobial activity reveals the synthesized compound biological activity.
Metal surfactant complexes have opened new horizons for scientific research as prospective alternatives for conventionally used bioactive organic compounds, which are often accompanied by severe side effects. The introduction of metal ions introduces dual functionality and expanded reactivity into the surfactant. They exhibit thrilling biological activities, however, their true potential for clinical applications has yet to be acknowledged. The metalloamphiphiles assemble to form aggregates, which themselves can act as therapeutically active agents due to their unique ability to bind to the DNA or proteins. Cationic surfactants having positive charges attached to surfaces, particles, polymers, peptides, or bilayers have been used as antimicrobial, antifungal, anticancer agents. These metal-based aggregates are known to inhibit proliferation and induce cell death by apoptosis or by necrosis in the cancer cells. The easily tunable amphiphiles thus offer a promising platform for versatile biological activities and reducing the complexity of multidrug administration.
The isocyanides CNC6H2R2-2,6-CHO-4 (1a–b) (a: R = Me; b: R = CHMe2), react with hydroxylamine, 2-pyridylhydrazine, and formylhydrazide to form CNC6H2R2-2,6-CHNOH-4 (2a–b), CNC6H2R2-2,6-CHNNH(2-C5H4N)-4 (3a–b), and CNC6H2R2-2,6-CHNNHCHO-4 (4b), respectively. The oxime and hydrazone derivatives 2–4 were chosen because of their potential for self-association via hydrogen bonding. Reaction of the isocyanides 1–4 (L) with FeI2, PdI2, and PtI2 affords complexes of the types trans-[FeI2(L4)], trans-[PdI2(L)2], and trans-[PtI2(L2)]. The molecular structures of the complexes trans-[FeI2(L4)] (L = 1b, 2a and 2b) and trans-[PdI2(L)2] (L = 2b) were determined by X-ray crystallography. The oxime derivatives form extended hydrogen bonded networks.
Density (rho), kinematic viscosity (nu), and absolute viscosity (eta) are presented for mixtures of ethane-1,2-diol and N,N-dimethylformamide from -10 to +80-degrees-C. The above properties were fitted by empirical equations stating their dependence on temperature and mole fraction of the mixture. Furthermore, some considerations regarding the meaning of the obtained adjustment parameters are made. The excess functions, such as molar volumes V(E), have been derived. The trends of V(E) data vs mole fraction of the mixtures have exhibited markedly negative deviations from ideality, indicating extensive molecular interactions between the components of the binary solvent system.
Three Schiff bases of racemic gossypol with L-amino acid methyl esters are synthesized and studied by FTIR and (1)H-NMR spectroscopy, and their structures are calculated by the PM3 semiempirical method. The Schiff bases in the study exist in the solid state and in solutions as enamine forms. The existence of diastereoisomers is very visible in the (1)H-NMR spectra. The amount of the diastereoisomers depends on the amount of time the solutions are rested in diffused light. The epimerization from D,L-isomer to L,L-isomer is very slow. The structures of the Schiff bases and the hydrogen bonds within these structures are discussed.
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