Synthesis, Characterization and Antimicrobial Studies of N1‐[(1E)‐1‐(2‐Hydroxyphenyl) ethylidene]‐2‐oxo‐2H‐chromene‐3‐carbohydrazide and its Metal Complexes
Abstract:A new complexes of the type ML, MʹL and M″L [where M=Cu(II), Co(II), Ni(II) and Mn(II), Mʹ=Fe(III) and M″=Zn(II), Cd(II) and Hg(II) and L=N1-[(1E)-1-(2-hydroxyphenyl)ethylidene]-2-oxo-2H-chromene- 3-carbohydrazide (HL)] Schiff base have been synthesized and characterized by elemental analysis, magnetic susceptibility, molar conductance, IR,1H NMR, UV-Visible and ESR data. The studies indicate the HL acts as doubly monodentate bridge for metal ions and form mononuclear complexes. The complexes Ni(II), Co(II), C… Show more
“…In ligand seven aromatic protons have been observed in the region δ (6.9–7.5) (m, 7H) as a multiplet, and it is shifted downfield in the Zn(II), Cd(II), and Hg(II) complexes. The signals observed at δ (2.5) are due to methyl protons that remain almost unaffected in Zn(II), Cd(II), and Hg(II) complexes indicating the nonparticipation of these groups in coordination [ 21 ].…”
Section: Resultsmentioning
confidence: 99%
“…They have been studied with the view to obtain more information on stereochemistry of the complexes and to procedure more support for the conclusion, deduced with the help of magnetic data. The Co(II) complex of the electronic absorption bands appears at 15384 and 20000 cm −1 due to 4 T 1g (F) → 4 A 2g (F) ( ν 2 ) and 4 T 1g (F) → 4 T 2g (P) ( ν 3 ) transitions, respectively, in an octahedral environment [ 22 ]. The band ν 1 could not be observed because of its very low intensity.…”
Section: Resultsmentioning
confidence: 99%
“…This is less than one, suggesting partial covalency in the metal ligand bond. The values Dq, β , β %, ν 2 / ν 1 , and LFSE suggest the octahedral geometry for Co(II) complex [ 24 ]. The Co(II) complex displays a magnetic moment value of 4.88 BM, which is within the range of 4.46–5.53 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.
“…In ligand seven aromatic protons have been observed in the region δ (6.9–7.5) (m, 7H) as a multiplet, and it is shifted downfield in the Zn(II), Cd(II), and Hg(II) complexes. The signals observed at δ (2.5) are due to methyl protons that remain almost unaffected in Zn(II), Cd(II), and Hg(II) complexes indicating the nonparticipation of these groups in coordination [ 21 ].…”
Section: Resultsmentioning
confidence: 99%
“…They have been studied with the view to obtain more information on stereochemistry of the complexes and to procedure more support for the conclusion, deduced with the help of magnetic data. The Co(II) complex of the electronic absorption bands appears at 15384 and 20000 cm −1 due to 4 T 1g (F) → 4 A 2g (F) ( ν 2 ) and 4 T 1g (F) → 4 T 2g (P) ( ν 3 ) transitions, respectively, in an octahedral environment [ 22 ]. The band ν 1 could not be observed because of its very low intensity.…”
Section: Resultsmentioning
confidence: 99%
“…This is less than one, suggesting partial covalency in the metal ligand bond. The values Dq, β , β %, ν 2 / ν 1 , and LFSE suggest the octahedral geometry for Co(II) complex [ 24 ]. The Co(II) complex displays a magnetic moment value of 4.88 BM, which is within the range of 4.46–5.53 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.
“…To assess the biological profile, another series of antimicrobial agents based on metals with a [(1E)-1-(2-hydroxyphenyl)ethylidene]-2-oxo-2H-chromene-3-carbohydrazide Schiff base possessing a NOO donor system was synthesized and thoroughly analyzed. Cd(II) complex showed the maximum zone of inhibition (18 and 16 mm) against E. coli and A. flavus organisms compared to [Cd(L)Cl 2 ]2H 2 O complex which showed the maximum zone of inhibition (27 and 31 mm) [ 37 , 38 ]. Co(II) complex of the same SB showed the maximum zone of inhibition (12 mm) against Staphylococcus aureus compared to [Co(L)H 2 OCl]Cl·6H 2 O complex which showed the maximum zone of inhibition (20 mm) [ 38 ].…”
Section: Resultsmentioning
confidence: 99%
“…Cd(II) complex showed the maximum zone of inhibition (18 and 16 mm) against E. coli and A. flavus organisms compared to [Cd(L)Cl 2 ]2H 2 O complex which showed the maximum zone of inhibition (27 and 31 mm) [ 37 , 38 ]. Co(II) complex of the same SB showed the maximum zone of inhibition (12 mm) against Staphylococcus aureus compared to [Co(L)H 2 OCl]Cl·6H 2 O complex which showed the maximum zone of inhibition (20 mm) [ 38 ].…”
Novel Schiff base ligand was prepared by the condensation of 2,2-(ethylenedioxy)bis(ethylamine) and imidazole-2-carboxaldehyde in a 1:2 ratio, and its complexes with Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), and Cd(II) metal ions were synthesized in a 1:1 ratio. Various methods were used to identify the Schiff base ligand and complexes. Characterization techniques such as infrared, UV, and
1
H NMR spectral tests, elemental analysis, molar conductivity, magnetic properties, thermal analysis, BET surface area, and theoretically by DFT were used to help further understanding of the complex structures. For all complexes, the ligand behaved as a neutral tetradentate ligand with NOON donor atoms and spectroscopic studies indicated an octahedral structure. The electrolytic behavior of the complexes was revealed by the molar conductivity measurements. In addition, thermogravimetric analysis was used to investigate the decomposition of the complexes and Schiff base ligand. According to the results obtained, the antibacterial activity of the metal complexes is higher than that of the Schiff base ligand against one or more bacterial species. The results showed that Cd(II) complex exhibits enhanced activity against
Aspergillus flavus
and Ni(II) complex against
Candida albicans
than the standard drug ketoconazole. The Mn(II) complex had stronger activity against human breast cancer cell line (MCF-7) than the other complexes. Antiviral drug development is critical in the latest outbreak of a novel coronavirus (SARS-CoV-2). The new coronavirus was screened using molecular docking.
Supplementary Information
The online version contains supplementary material available at 10.1007/s13738-021-02359-w.
Mononuclear chelates of Cr(III), Mn(II), Fe(III), Ni(II), Cu(II), Zn(II) and Cd(II) resulting from new tridentate Schiff base ligand , 4-((1-(5-acetyl-2,4-dihydroxyphenyl)ethylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one, were synthesized and characterized via various spectroscopic methods. Metal to ligand ratio was found to be 1:1, which was revealed via elemental analysis. IR has sharp out that the coordination of the ligand towards the metal ions was carried out via NOO atoms. UV-Vis, 1 HNMR spectral data, molar conductance measurements, BET surface area, melting points and theoretically through density function theory were used such as characterizing techniques in supporting of further interpretation of the complexes structures. The complexes were octahedral except Cu(II) and Ni(II) complexes were tetrahedral as suggested through the magnetic moment measurement. The complexes were found to have surface area, pore volume and particle radius 23-176 m 2 g -1 , 0.02-0.33 cc/g and 8.71-4.32 nm, respectively, as pointed out from BET measurement. Schiff base ligand and its metal complexes were tested in vitro to estimate their bactericidal activity opposed to Gram-negative and Gram-positive bacteria and antifungal organisms. In the recent incident of a novel coronavirus (SARS-CoV-2) spreads, antiviral drug detection is of most importance. MOE 2008 was used headed for screen potential drugs with molecular docking by the structural protein and non-structural protein sites of new coronavirus and the study was constructed to molecular docking without validation through MD simulations. Interactions with the main protease may play a key role in fighting against viruses.
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