(E)3-2-(1-(2,4-Dihydroxyphenyl)ethyldeneamino)phenyl)-2-methylquinazoline-4(3H)-one Schiff Base and Its Metal Complexes: A New Drug of Choice against Methicillin-ResistantStaphylococcus aureus
Abstract:The 3-(2-aminophenyl) quinazolin-2-methyl-4(3H)-one and 2,4-dihydroxyacetophenone undergo condensation to afford (E)3-2-(1-(2,4-dihydroxyphenyl)ethyldeneamino)phenyl)-2-methylquinazoline-4(3H)-one Schiff base (DHPEAPMQ). The newly synthesized Schiff base (DHPEAPMQ) and its metal complexes were evaluated for their antimicrobial activity against methicillin-resistant Staphylococcus aureus isolated from the Gulbarga region in India. The Cu(II), Ni(II), and Zn(II) complexes of Schiff base (DHPEAPMQ) showed good an… Show more
“…Racah parameter B ′ is less than the free ion value of 1040 cm −1 indicating the covalent character of the complex. The ratios ν 2 / ν 1 and β % further support the octahedral geometry around the Ni(II) ion [ 26 ]. The Ni(II) complex showed the magnetic moment value of 3.00 BM, which is within the range of 2.7–3.3 BM.…”
The Schiff base ligand 5-bromo-3-(((8-hydroxy-2-methylquinolin-7-yl)methylene)hydrazono)indolin-2-one (BHMQMHI) was prepared via condensation of 5-bromo-3-hydrazonoindolin-2-one and 7-formyl-8-hydroxy-2-methylquinoline and its Co(II), Ni(II), Cu(II), Zn(II), Cd(II), and Hg(II) complexes have been synthesized and characterized by elemental analysis, conductance data, magnetic susceptibility measurements, IR, UV-Vis, mass spectrometry, 1H NMR, ESR, XRD, and thermal studies. By these spectral studies it is found that Co(II), Ni(II), and Cu(II) complexes have exhibited octahedral geometry whereas the Zn(II), Cd(II), and Hg(II) complexes have exhibited tetrahedral geometry. Potentiometric studies have been carried out on complexes of Schiff base (BHMQMHI) with Cu(II), Co(II), and Ni(II). Calvin-Bjerrum pH-titration technique as used by Irving and Rossotti has been applied to determine stability constants in mixed solvents at 25 ± 1°C. The present study reports the protonation constants of this ligand and stability constants of its metal complexes in dioxane-water (50%, v/v) mixtures. Metal-ligand stability constants fall in the order of Cu(II) > Co(II) > Ni(II) which is in agreement with those reported by Irving stability order. The Schiff base (BHMQMHI) and its metal complexes have been screened for their in vitro antibacterial and antifungal activities by minimum inhibitory concentration (MIC) method. The DNA cleavage activities of all the complexes were studied by agarose gel electrophoresis method. In addition, the free ligand along with its complexes has been studied for their antioxidant activity.
“…Racah parameter B ′ is less than the free ion value of 1040 cm −1 indicating the covalent character of the complex. The ratios ν 2 / ν 1 and β % further support the octahedral geometry around the Ni(II) ion [ 26 ]. The Ni(II) complex showed the magnetic moment value of 3.00 BM, which is within the range of 2.7–3.3 BM.…”
The Schiff base ligand 5-bromo-3-(((8-hydroxy-2-methylquinolin-7-yl)methylene)hydrazono)indolin-2-one (BHMQMHI) was prepared via condensation of 5-bromo-3-hydrazonoindolin-2-one and 7-formyl-8-hydroxy-2-methylquinoline and its Co(II), Ni(II), Cu(II), Zn(II), Cd(II), and Hg(II) complexes have been synthesized and characterized by elemental analysis, conductance data, magnetic susceptibility measurements, IR, UV-Vis, mass spectrometry, 1H NMR, ESR, XRD, and thermal studies. By these spectral studies it is found that Co(II), Ni(II), and Cu(II) complexes have exhibited octahedral geometry whereas the Zn(II), Cd(II), and Hg(II) complexes have exhibited tetrahedral geometry. Potentiometric studies have been carried out on complexes of Schiff base (BHMQMHI) with Cu(II), Co(II), and Ni(II). Calvin-Bjerrum pH-titration technique as used by Irving and Rossotti has been applied to determine stability constants in mixed solvents at 25 ± 1°C. The present study reports the protonation constants of this ligand and stability constants of its metal complexes in dioxane-water (50%, v/v) mixtures. Metal-ligand stability constants fall in the order of Cu(II) > Co(II) > Ni(II) which is in agreement with those reported by Irving stability order. The Schiff base (BHMQMHI) and its metal complexes have been screened for their in vitro antibacterial and antifungal activities by minimum inhibitory concentration (MIC) method. The DNA cleavage activities of all the complexes were studied by agarose gel electrophoresis method. In addition, the free ligand along with its complexes has been studied for their antioxidant activity.
“…The solution of compound (ZA) was gradually added to the aldehyde-containing acid solution while stirring. At the end of this time, the cooling of the mixture with crushed ice yielded the colored powder, which was separated by filtration and then recrystallized using absolute% ethanol to obtain the final compounds (ZA1-ZA6) (21) .…”
Section: General Procedures For the Synthesis Of Quinazolinone Schiff...mentioning
New series of 4-aminophenyl quinazolinone attached to an aromatic aldehyde moiety has been designed. Compound (ZA) was synthesized by a reaction of benzene-1,4-diamine with 2-aminobenzoic acid.
The reaction between (ZA) intermediate and different substituted aromatic aldehydes (R1- R6) is considered one of the most common chemical reactions for the synthesis of imine compounds (Schiff bases) to produce compound (ZA1-ZA6). FTIR, 1H-NMR, and 13C-NMR have been used to confirm the chemical structures of various substances. MTT assay was used to assess in vitro anti-proliferative action for estrogen receptor alpha. The anti-proliferative study discovered a dose-dependent effect on cell proliferation in breast cancer (MCF-7) with inhibitory concentration In comparison to the reference medication tamoxifen (IC50 of 133.4µg\mL), IC50 of the compounds (ZA1, ZA2, ZA3) was 0.07964, 57.43 & 0.002717 µg\mL, respectively at 72 hours on same cell line mentioned above, that also signifies that compound ZA1 has a significantly greater effect on this cell line type
This review aims to shed light on the profound implications of Schiff Bases in combating a
spectrum of pathogens by delving into their complex classification, synthesis, and reactions. The investigation
also covers the varied molecular properties of Schiff bases, highlighting their potential
use as chelating agents in coordination chemistry. Moreover, the investigation explores the discerning
nature of Schiff Bases about metal ions and their adeptness in establishing intricate associations,
highlighting their significance in metal coordination chemistry and specialized pharmaceutical
transport mechanisms. Moreover, the review delves into the synthetic capacity of Schiff Bases, highlighting
their importance in synthetic methodologies due to their exceptional adaptability, selectivity,
and structural similarity to organic compounds. The methodology employs a rigorous systematic literature
review to understand Schiff Bases comprehensively. This involves a meticulous analysis of
various research articles and publications, allowing for a comprehensive exploration of the topic. The
assessment of experimental investigations contributes to comprehending their molecular attributes,
specificity for metal ions, and capacity for synthesis. The presented analysis amalgamates a multitude
of sources to provide a nuanced and comprehensive viewpoint on the subject matter of Schiff Bases.
The findings underscore the multifaceted utility of Schiff Bases in the fight against pathogens, their
adaptability as chelating compounds, and their discerning affinity for metal ions. The examination of
synthesis highlights their profound importance in synthetic methodologies and their striking resemblance
to compounds found in living organisms. In conclusion, this analysis reveals Schiff Bases as
highly adaptable compounds with potential in antimicrobial therapy, coordination chemistry, and
precision drug delivery. The distinctive molecular attributes of these substances, functioning as chelators,
contribute to their notable importance. The ability of Schiff bases to form complexes and their
preference for metal ions highlight the wide range of applications for these molecules. Schiff Bases
have a transformative effect on chemistry and medicine as we investigate their synthetic potential,
driven by their versatility and structural similarity to biological compounds.
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