Four novel Cu(II) chelates were synthesized by reacting hydrated CuCl2 and Cu(CH3COO)2 with two derivatives of 1,3,4‐thiadiazolethiosemicarbazone. The structures and geometries of the synthesized complexes were deduced applying the alternative analytical and spectral tools confirming the complexes to have the formulae [(LH)Cu(Cl)]•0.5H2O, [(LH)Cu(OAc)(H2O)2]•0.5H2O, [(LCl)Cu(Cl)(H2O)2]•H2O and [(LCl)Cu(OAc)]; where LH and LCl are phenyl and p‐chlorophenyl derivatives of 1,3,4‐thiadiazolethiosemicarbazone ligands, respectively (deprotonated form). IR spectral data confirmed the coordination of the ligands to the copper center as monobasic tridentate in the thiol form. Thermal analysis, UV–Vis spectra and magnetic moment assured the geometry around the copper center to be square planar, trigonal bipyramid and octahedral which have been confirmed by the computational studies. The two ligand derivatives and their copper complexes were applied to evaluate their binding modes with SS‐DNA via UV–Vis spectral titration and viscosity measurements. The DNA‐binding constant (kb) values of the investigated derivatives were calculated and compared with ethidium bromide in order to assess their mode of binding with DNA. Moreover, docking study of these complexes was carried out to recognize the drug–DNA interactions and to calculate their binding energies.
The two azo dye ligands named 4‐(2,4‐dihydroxy‐5‐formylphen‐1‐ylazo)‐N‐thiazol‐2‐yl‐benzenesulfon amide (H3TPBS) and 4‐(2,4‐dihydroxy‐phenylazo)‐N‐(3,4‐dimethyl‐1,2‐oxazol‐5 yl)benzenesulfonamide (H3IPBS) were employed for the synthesis of a series of Cu(II) chelates through the reaction of the ligands with Cu(II) salts of different anions. Full structure affirmation of all complexes has been done. Analytical results confirmed the formation of the metal chelates in the molar ratio 2:1 (M:L). Ultraviolet–visible spectra and magnetic moment proved the formation of complexes in square planar and square pyramidal geometries. Antimicrobic activity of the synthesized complexes has been assigned and compared with their parent ligands and also compared with standard antibiotic drugs showing enhanced activity over both the ligands and the standard drugs. The antitumor efficacy of the complexes has been also evaluated contra the two cell lines A‐549 cells (human Lung cancer cell line) and Panc‐1 (Pancreatic carcinoma) and compared with the standard drug Vinblastine. Additionally, The Cu(II) chelates were examined for their activity in oxidation coupling of o‐aminophenol (OAP) to 2‐aminophenoxazine‐3‐one (APX) in DMF solvent in open air atmosphere. The examined complexes afforded low to relatively high efficiency with TOF number from 0.27–78.12 h−1 with increased activity for complexes 1, 3, 5 and 7 incorporating Cl− or NO3− anions in their first coordination sphere.
The present work discusses the synthesis and structure elucidation of azo ligand named 3,4‐dimethylisoxazol‐5‐yl‐4‐((3‐formyl‐4‐hydroxyphenyl)diazenyl) benzenesulfonamide (abbreviated as MIBS). MIBS ligand has been employed for the synthesis of a series of transition metal chelates in which the transition metal incorporated are Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II). The isolated metal chelates have been demonstrated to be formed in 1:1 (M:L) ratio for all complexes excluding the Cd(II) chelate which have 1:2 (M:L) composition. The mode of bonding of the ligand towards the metal centre has been concluded from inspection of the FTIR spectra of both ligand and complexes, providing that the ligand attached to the meal centres through the carbonyl and deprotonated hydroxyl oxygen atoms. The geometry of the formed complexes has been proved to be tetrahedral for Mn(II), Co(II), Zn(II) and Cd(II) compounds and octahedral for the remaining chelates. Bioassay investigation of the synthesized compounds against Gram‐negative and Gram‐negative bacteria and fungi has been performed in comparison with familiar standard drugs. Among the tested compounds, Cd(II) and Co(II) complexes showed the highest activity against the tested microorganisms, which is in good matching with docking studies. The interaction manner of the isolated compounds with SS‐DNA has been inspected by means of electronic absorption titration and viscosity studies.
A series of divalent and one trivalent metal chelates of the azo ligand resulting from coupling of sulfafurazole diazonium chloride with resorcinol have been designed and synthesized. Structure investigation of the isolated chelates have been achieved by applying spectroscopic and analytical tools which collaborated to assure the formation of the metal chelates in the molar ratios of 1L: 1M for Ni(II), Co(II), and Fe(III) chelates, where Cu(II) and Zn(II) complexes formed in the ratio 2L : 1M. The geometrical arrangement around the metal canters was concluded from UV-Vis spectra to be octahedral for all metal chelates. The attachment of the ligand to the metal ions took place through the azo group nitrogen and o-hydroxyl oxygen through proton displacement leading to the ligand being in monobasic bidentate binding mode. Antimicrobial and antitumor activities of the interested compounds have been evaluated against alternative microorganisms and cancer cells, respectively, in a trial to investigate their extent of activity in addition to docking studies. The mode of interaction of the compounds with SS-DNA has been examined by UV-Vis spectra and viscosity studies.
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