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In this study, we prepared the macrocyclic Schiff base ligand (L) derived from 1,4-dicarbonylphenyl-dihydrazide and pentane-2,4-dione (2:2) and its CoII, CuII and NiII complexes. The compounds were characterized by the analytical and spectroscopic methods like elemental analysis, molar conductance measurements, mass spectrometry, 1H nuclear magneti...
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We describe herein a fast and rapid technique for preparation of ligand 2-(1,2,4-triazol-3-ylimino)methyl)-6-methoxyphenol under microwave irradiation. The microwave methodology is rapid, convenient, proceeds under mild conditions, and gives a better yield (80–98%) and high purity of the title compounds. The prepared Schiff base was used for furthe...
A novel series of Pd(II), Pt(II), Hg(II) and Zn(II) complexes have been synthesized from the Schiff base. Structural features were determined by analytical and spectral techniques like IR, 1 H NMR, elemental analysis. The metal complexes were subjected to degradation of Janus Green B dye using prepared metal complexes 6a-d. The catalytic degradatio...
The synthetic, structural, spectroscopic and analytical properties of steric hindered Schiff-base ligand [N-(3,5-di-tertbutylsalicylaldimine)- 1-(2-Aminoethyl) piperazine (HL)] and its mononuclear Cu(II), Co(II) and Ni(II) complexes are described. The new unsymmetric steric hindered Schiff base ligand containing a donor set of NONO was prepared by...
The synthetic, structural, spectroscopic and analytical properties of steric hindered Schiff-base ligand [N-(3,5-di-tert-butylsalicylaldimine)-1-(2-Aminoethyl) piperazine (HL)] and its mononuclear Cu(II), Co(II) and Ni(II) complexes are described. The new unsymmetric steric hindered Schiff base ligand containing a donor set of NONO was prepared by...
We report here the synthesis, characterization, and antibacterial evaluation of transition metal complexes of Ni, Cu, Co, Mn, Zn, and Cd (6a–f), using a Schiff base ligand (5) derived from naproxen (an anti-inflammatory drug) and 5-bromosalicylaldehyde by a series of reactions. The ligand and the synthesized complexes were characterized by elementa...
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... Among all the synthesized compounds, the meta-halogenated vanillin showed good inhibition against both Gram-positive and Gram-negative bacteria. This is due to the synergistic effects of hydrophilic-lipophilic characteristics in the molecule thus contributing to the antibacterial properties [35]. The aromatic rings in the molecular network have also played a significant role in enhancing the lipophilic properties which also can potentially interact with the hydrophobic areas of bacterial enzymes [21]. ...
Lead compounds containing nitrogen pharmacophores from natural resources have garnered interest among researchers due to their potential for drug development. However, the extractions of the active metabolites are usually labor-intensive and time-consuming. In this study, halogenated vanillin derivatives featuring azo dyes (N=N) (1a-1 h) and Schiff base (C=N) (2a-2 h) have been synthesized via diazonium coupling and nucleophilic substitution reaction, respectively. The comparative effect of N=N and C=N moieties was evaluated for antibacterial properties against Staphylococcus aureus and Escherichia coli via disc diffusion method. Incorporating C=N (8–13 mm) into the vanillin network showed excellent inhibition against S. aureus compared to N=N (7–8 mm) and the standard ampicillin (12 mm). While the halogenated vanillin featuring N=N (7–9 mm) and C=N (7–8 mm) moieties showed excellent zone of inhibitions against E. coli compared to the parent vanillin. The in-silico screening using AutoDock Vina, showed 2c-h (inhibition zone > 10 mm) with a high binding affinity against DNA gyrase enzyme with binding energy ranging from − 7.3 to − 7.9 kcal/mol, similar to re-docking of ampicillin − 7.6 kcal/mol and co-crystalize compounds BPH651 with − 7.5 kcal/mol. This research contributes a significant milestone in drug design, especially for the development of new antibacterial drugs with outstanding properties.
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... Only small hydrophilic solutes may pass through the cell wall because of the profusion layers of proteins that act as hydrophilic transmembrane channels. In other words, a synergistic relationship between a molecule's hydrophilic and lipophilic properties is crucial in antibacterial activity for drug development (Ngaini et al. 2022;Gull and Hashmi 2015). ...
Chemical modification of active scaffolds from natural products has gained interest in pharmaceutical industries. Nevertheless, the metabolites extraction is time-consuming while the lead is frequently mismatched with the receptor. Here, the diazo coupling approach was introduced to generate a series of vanillin derivatives featuring halogenated azo dyes (1a-h). The vanillin derivatives showed effective inhibition of S. aureus (7-9 mm) and E. coli (7-8 mm) compared to the parent vanillin, while 1b had the highest inhibition zone (9 mm) against S. aureus comparable to the reference ampicillin. The presence of N = N, C = O, -OH, -OCH3 and halogens established strategic binding interactions with the receptor. The potential vanillin-azo as an antimicrobial drug was supported by in silico docking with penicillin-binding proteins and DFT (using Gaussian 09) with binding affinity -7.5 kcal/mol and energy gap (Egap) 3.77 eV, respectively. This study represents a significant advancement in drug discovery for effective antibiotics with excellent properties.
... The complexes of divalent cobalt, nickel, copper, zinc, cadmium, and mercury were studied and characterized with a Schiff base ligand derived from the reaction of 2hydroxybenzohydrazide with 2-hydroxy-1-naphthaldehydecarboxaldehyde, then reacting the prepared ligand with chloride ions mentioned above to form metal complexes in a ratio The determination of the elements cobalt (II), nickel (II) copper(II) zinc (II) and cadmium (II) by a spectrophotometric method using an atomic absorption spectrometer, (21) ). and when it bonds with the metal ion, it shifted to lower frequencies (1595-1541cm -1 ), which indicates the coordination of the nitrogen atom of the isomethine group with the metal ions (22,23,24) .The spectrum of infrared showed the stretching frequency of the group (C=O) at the region (1687 cm -1 ), and when forming the complexes, the band appeared at a lower frequency than the ligand band at (1681-1620cm -1 ), which indicates the participation of the oxygen atom of the carbonyl group in coordination with the metal ions of the prepared complexes. (25,26) The stretching frequency of the hydroxyl group (OH) appeared as a ( لعدد ا ، 1 لسنة ،) 2023 ...
... Macrocycles are interesting ligands since they are good hosts for a variety of metal ions, neutral molecules and organic cation guests. 2,4,5,9 The hostguest chemistry of metal -ions and macrocycles is quite important in fundamental studies like phase-transfer catalysis. 3 Macrocyclic coordination compounds are assumed to mimic the synthetic models of metalloporphyrin's and metallocorrins because of their intrinsic structural properties. ...
A novel macrocyclic Schiff base ligand 1,4,8,11-tetraaza-2,3,9,10-tetramethyl cyclotetradeca-1,3,8,10-tetraene was synthesized by condensation between butane-2,3-dione and propane-1,3-diamine in an alcoholic medium. The complexes of Co(II), Ni(II), Cu(II) and Zn(II) with Schiff base have been prepared from metal salts in an alcoholic medium. The synthesized Schiff base and its metal complexes are characterized by elemental analysis, molar conductance measurements, magnetic susceptibility, FTIR and electronic absorption spectral data. The higher molar conductance values of these metal complexes show their electrolytic nature. The Schiff base behaves as tetradentate ligand. The general molecular formula of the metal complexes has been found to be [M(L)(X)2] where M= Co(II), Ni(II), Cu(II) and Zn(II) , L=Schiff base and X= water, chlorine and ethanol . Thus, on the basis of elemental analysis and spectral studies octahedral geometry was assigned to metal complexes. The synthesized metal complexes showed more antimicrobial activity than free Schiff base ligand.
... According to the results, metal complexes are more effective against bacteria than ligands. Among all the complexes Ni complex is found to be more active against all species as it shows the same MIC value (4 μg/mL) to the standard antibiotic Amikacin against Bacillus subtilis [65]. ...
The World is facing an epidemic of various diseases caused by viruses, bacteria, and fungi. Apart from it, cancer, malaria, and diabetes are some major health problems. So, a need arises to discover novel molecules that can be used as therapeutic drugs for several diseases, including cancer and diabetes. Macrocyclic Schiff base (MSB) transition metal complexes are popularly studied organometallic compounds due to their vast biological applications in treating infectious diseases and various health problems. This attracts the researchers to the Chemistry of Schiff base metal complexes in pharmaceutical applications and areas like biochemical, bio-inorganic, environmental, industrial, photochemical, photophysical, photoelectronic etc. So, the Novel synthesis of Schiff base metal complexes will design and develop more effective therapeutic drugs. Even though the topic is quite old and exploited, many researchers are still globally working to find new MSB complexes and their applications. Based on the above considerations, we have reviewed the pharmaceutical properties of MSB transition metal complexes synthesized in the last two decades.
... A significant number of metal complexes of different macrocycles [18,19,20], including, those relevant to the present investigation, 14-membered octamethyl tetraazamacrocyclic diene ligand (Me 8 [14] diene), isomeric ligands (L A , L B , and L C ) and their N-pendent derivative ligands, are available in the literature [21,22,23,24,25,26]. In this context, copper(II) and nickel(II) complexes with bis-hydroxyethyl (L BY and L CY ) and dimethyl (L BZ and L CZ ) derivatives of the isomeric ligands L B and L C have been studied [23,24]. ...
... The UV-visible spectra did not exhibit any d-d bands but displayed charge transfer bands as expected for d 10 system. Consistent with previous work, the stereochemistry of the compounds does not change during axial substitution reactions [19], so the stereochemistry of axial ligand substitution products of [Cd(L CX ) (ClO 4 ) 2 ]2H 2 O were assigned by comparison with the 1 H-NMR data of [Cd(L CX ) (ClO 4 ) 2 ]2H 2 O. ...
The isomeric ligand LC, a saturated analogue of 2,9-C-meso-Me8[14]diene, on reflux with excess acrylonitrile afforded 1,8-N-pendant cyanoethyl derivative LCX. Interaction of LCX with cadmium(II) perchlorate, nitrate, acetate, and chloride salts produced six coordinated octahedral compounds, [Cd(LCX)(ClO4)2]∙2H2O, [Cd(LCX)(NO3)2], [Cd(LCX)(CH3COO)2], and [Cd(LCX)Cl2], respectively. Further, axial substitution reactions between [Cd(LCX)(ClO4)2]∙2H2O and KI, KBr, KCl, KSCN, and NaNO2 in a 1:2 ratio yielded six coordinated octahedral compounds, [Cd(LCX)I2]∙H2O, [Cd(LCX)Br2]∙2H2O, [Cd(LCX)Cl(ClO4)]∙2H2O, [Cd(LCX)(NCS)2]∙H2O, and [Cd(LCX)(NO2)(ClO4)]∙2H2O, respectively. All of the newly prepared compounds have been characterized by analytical, spectroscopic, molar conductivity, and magnetochemical data. The crystal structure of the ligand LCX was determined by x-ray crystallography which showed the 14-membered ring to adopt an extended chair conformation. Antibacterial activities of the newly formed cadmium(II) complexes against selected bacteria showed these to exhibit moderate and selective activity with 1-4 and 8 exhibiting greatest potency against the gram negative bacterium Salmonella typhi, and 5, 6, and 7 against the gram positive bacterium Bacillus wiedmannii.
... This formation is similar to biological molecules such as hemoglobin, chloroprene, catalytically enzyme and vitamin B12. Most complexes of macrocyclic Schiff base ligand stable with a high oxidation state of metal ion, slow coordination reaction, and high thermal stability [5,6]. The development of transition metal reaction with macrocyclic ligand encountered some difficulties; for example, most non-transition metals react with large ring ligands such as Pb(II), Ba(II) and Ag(II), the transmetallation technique has been used to form the same complex with a transition metal, in this case, the complexes of non-transition metal must be dissolved completely in the solvent [2,7]. ...
New series of Schiff base macrocyclic complexes have been prepared through a new chemical approach. Firstly, ligand Bis (2,6-diamine pyridine 2,5-hexanedione (DP-HD) prepared via reacting of 2,6-diamine pyridine (DP) with 2,5-hexanedione(HD) in molar ration (1DP:1HD). The complexes of this ligand include Mn (II), Fe (II), Co (II), Ni (II) and Cu (II) as central metal ions also prepared with a molar ratio of (1 ligand:1 metal ion). Metals chloride was used as raw materials for this preparation. A variety of spectral and physical techniques were applied to characterize the macrocyclic complexes such as 1H-NMR, FT-IR, UV-Vis, CHN analysis, conductivity, Atomic absorption and magnetic susceptibility. Depending on spectral and magnetic measurements, the suggested geometrical shapes of these complexes were reported. FT-IR spectroscopy recorded the coordination sites based on the ligand's main group bands that could shift to a lower frequency. Finally, thermal stability has been investigated for ligands and their complexes. While the thermal gravimetric analyses (TGA) and differential thermal analyses (DTA) approved the stability of these compounds if compared to their ligands only.
... This formation is similar to biological molecules such as hemoglobin, chloroprene, catalytically enzyme and vitamin B12. Most complexes of macrocyclic Schiff base ligand stable with a high oxidation state of metal ion, slow coordination reaction, and high thermal stability [5,6]. The development of transition metal reaction with macrocyclic ligand encountered some difficulties; for example, most non-transition metals react with large ring ligands such as Pb(II), Ba(II) and Ag(II), the transmetallation technique has been used to form the same complex with a transition metal, in this case, the complexes of non-transition metal must be dissolved completely in the solvent [2,7]. ...
New series of Schiff base macrocyclic complexes have been prepared through a new chemical approach. Firstly, ligand Bis (2,6-diamine pyridine 2,5-hexanedione (DP-HD) prepared via reacting of 2,6-diamine pyridine (DP) with 2,5-hexanedione(HD) in molar ration (1DP:1HD). The complexes of this ligand include Mn (II), Fe (II), Co (II), Ni (II) and Cu (II) as central metal ions also prepared with a molar ratio of (1 ligand:1 metal ion). Metals chloride was used as raw materials for this preparation. A variety of spectral and physical techniques were applied to characterize the macrocyclic complexes such as 1H-NMR, FT-IR, UV-Vis, CHN analysis, conductivity, Atomic absorption and magnetic susceptibility. Depending on spectral and magnetic measurements, the suggested geometrical shapes of these complexes were reported. FT-IR spectroscopy recorded the coordination sites based on the ligand's main group bands that could shift to a lower frequency. Finally, thermal stability has been investigated for ligands and their complexes. While the thermal gravimetric analyses (TGA) and differential thermal analyses (DTA) approved the stability of these compounds if compared to their ligands only.
... This formation is similar to biological molecules such as hemoglobin, chloroprene, catalytically enzyme and vitamin B12. Most complexes of macrocyclic Schiff base ligand stable with a high oxidation state of metal ion, slow coordination reaction, and high thermal stability [5,6]. The development of transition metal reaction with macrocyclic ligand encountered some difficulties; for example, most non-transition metals react with large ring ligands such as Pb(II), Ba(II) and Ag(II), the transmetallation technique has been used to form the same complex with a transition metal, in this case, the complexes of non-transition metal must be dissolved completely in the solvent [2,7]. ...
New series of Schiff base macrocyclic complexes have been prepared through a new chemical approach. Firstly, ligand Bis (2,6-diamine pyridine 2,5-hexanedione(DP-HD) prepared via reacting of 2,6-diamine pyridine (DP) with 2,5-hexanedione(HD) in molar ration (1DP:1HD). The complexes of this ligand include
Mn (II), Fe (II), Co (II), Ni (II) and Cu (II) as central metal ions also prepared with a molar ratio of (1 ligand:1 metal ion). Metals chloride was used as raw materials for this preparation. A variety of spectral and physical techniques were applied to characterize the macrocyclic complexes such as 1H-NMR, FT-IR, UV-Vis, CHN
analysis, conductivity, Atomic absorption and magnetic susceptibility. Depending on spectral and magnetic measurements, the suggested geometrical shapes of these
complexes were reported. FT-IR spectroscopy recorded the coordination sites based on the ligand's main group bands that could shift to a lower frequency. Finally, thermal stability has been investigated for ligands and their complexes. While the thermal gravimetric analyses (TGA) and differential thermal analyses (DTA)
approved the stability of these compounds if compared to their ligands only.
... Some macrocyclic complexes have been reported to exhibit potential antibacterial and antifungal activities. 4,5 Prompted by these applications, in the present paper, we wish to report the macrocyclic complexes synthesized from 3,4-diaminotoluene and acetylacetone and their antibacterial, antifungal and antioxidant activities. [6][7][8] Furthermore, the removal of methylene blue dye from aqueous solution by using iron complexes was also studied. ...
... In contrast, complex 5 registered the least antioxidant activity. Higher antioxidant activity observed in Cr(III) complexes (d 3 ) may be attributed to their virtue of more electron affinity as compared to half-filled Fe(III) (d5 ) complexes. 19 Fig.-6: Best Docking Score (Run 3rd: -8.18 kcal/mol) of the interaction of [Fe(C24H28N4)NO3](NO3)2 with hydrolase from Paenibacillus polymyxa.Table-6: Percentage Antioxidant Activity of the ComplexesCONCLUSIONMacrocyclic complexes of Cr(III) and Fe(III) metal ions were synthesized and characterized with the help of various spectroscopic and physicochemical techniques. ...
A new series of macrocyclic complexes have been synthesized by template condensation between 3,4- diaminotoluene and acetylacetone in the presence of trivalent metal ions to form macrocyclic complexes having four coordination sites. Different spectroscopic and physicochemical techniques were used to establish the geometry and structural framework of the synthesized macrocyclic complexes. Further, these complexes were also investigated for their antibacterial, antifungal and antioxidant activities. Removal of methylene blue dye from the aqueous by iron complexes was also investigated.
