Metal‐based sulfonamides: synthesis,characterization, antibacterial,antifungal and cytotoxic properties of pyrrolyl‐ and thienyl‐derived compounds

Pyrrolyl and thienyl derived sulfonamides and their metal [cobalt(II), copper(II), nickel(II) and zinc(II)] complexes were synthesized and characterized by elemental analyses, molar conductances, magnetic moments, IR, ¹H NMR, ¹³C NMR and electronic spectral data. These compounds were screened for in‐vitro antibacterial activity against four Gram‐negative (Escherichia coli, Shigella flexeneri, Pseudomonas aeruginosa and Salmonella typhi) and two Gram‐positive (Bacillus subtilis and Staphylococcus aureus) bacterial strains, and for in‐vitro antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani and Candida glaberata. The results of these studies revealed that all compounds showed significant to moderate antibacterial activity; however, the zinc complexes were shown to be the most active against various species. The brine shrimp bioassay was also carried out to study their in vitro cytotoxic properties of all the synthesized ligands and their metal complexes. Only two compounds ( 14 and 19 ) displayed potent cytotoxic activity as LD₅₀ = 5.5637 × 10^?4 and 4.4023 × 10^?4 M ml^?1 respectively, against Artemia salina. Copyright © 2007 John Wiley & Sons, Ltd.     

Metal‐based antibacterial and antifungal amino acid derived Schiff bases: their synthesis,characterization and in vitro biological activity

A new series of antibacterial and antifungal amino acid derived Schiff bases and their cobalt(II), copper(II), nickel(II) and zinc(II) metal complexes have been synthesized and characterized by their elemental analyses, molar conductances, magnetic moments, IR and electronic spectral measurements. The spectral data indicated the Schiff base ligands ( L ₁– L ₅) derived by condensation of salicylaldehyde with glycine, alanine, phenylalanine, methionine and cysteine, to act as tridentate towards divalent metal ions (cobalt, copper, nickel and zinc) via the azomethine‐N, deprotonated carboxyl group of the respective amino acid and deprotonated oxygen atom of salicylaldehyde by a stoichiometric reaction of M: L (1:2) to form complexes of the type K₂[M( L )₂] [where M = Co(II), Cu(II), Ni(II) and Zn(II)]. The magnetic moments and electronic spectral data suggested that all complexes have an octahedral geometry. Elemental analyses and NMR spectral data of the ligands and their Zn (II) complexes agree with their proposed structures. The synthesized ligands, along with their metal complexes, were screened for their in‐vitro antibacterial activity against four Gram‐negative (Escherichia coli, Shigella flexeneri, Pseudomonas aeruginosa and Salmonella typhi) and two Gram ‐ positive (Bacillus subtilis and Staphylococcus aureus) bacterial strains and for in‐vitro antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani and Candida glaberata. The results of these studies show the metal complexes to be more antibacterial/antifungal against one or more species as compared with the uncomplexed Schiff base ligands. The brine shrimp bioassay was also carried out to study their in‐vitro cytotoxic properties. Only three compounds ( 2, 11 and 17 ) displayed potent cytotoxic activity as LD₅₀ = 8.196 × 10^?4, 7.315 × 10^?4 and 5.599 × 10^?4 M /ml respectively, against Artemia salina. Copyright © 2007 John Wiley & Sons, Ltd.     

Synthesis,characterization and biological properties of sulfonamide‐derived compounds and their transition metal complexes

Sulfonamide‐derived compounds and their first row d‐transition metal chelates [cobalt(II), copper(II), nickel(II) and zinc(II)] have been synthesized and characterized. The nature of bonding and structure of all the synthesized compounds have been proposed from magnetic susceptibility and conductivity measurements, IR, ¹H and ¹³C NMR, electron spectra, mass spectrometry and CHN analysis data. The structure of ligand, 4‐{[(E)‐(5‐chloro‐2‐hydroxyphenyl) methylidene] amino}‐N‐(4,6‐dimethyl pyrimidin‐2‐yl) benzene sulfonamide has also been determined by X‐ray diffraction method. An octahedral geometry has been suggested for all the complexes. The ligands and metal complexes have been screened for their in vitro antibacterial, antifungal and cytotoxic activity. The results of these studies revealed that all compounds showed moderate to significant antibacterial activity against one or more bacterial strains and good antifungal activity against various fungal strains. Copyright © 2009 John Wiley & Sons, Ltd.     

Sulfonamide‐derived compounds and their transition metal complexes: synthesis,biological evaluation and X‐ray structure of 4‐bromo‐2‐[(E)‐{4‐[(3,4‐dimethylisoxazol‐5 yl)sulfamoyl]phenyl} iminiomethyl] phenolate

Sulfonamide‐derived new ligands, 4‐({[(E)‐(5‐bromo‐2‐hydroxyphenyl)methylidene]‐amino}methyl)benzenesulfonamide and 4‐bromo‐2‐((E)‐{4‐[(3,4‐dimethylisoxazol‐5‐yl)sulfamoyl]phenyl}iminiomethyl)phenolate and their transition metal [cobalt(II), copper(II), nickel(II) and zinc(II)] complexes were synthesized and characterized. The nature of bonding and structure of all the synthesized compounds were deduced from physical (magnetic susceptibility and conductivity measurements), spectral (IR, ¹H and ¹³C NMR, electronic, mass spectrometry) and analytical (CHN analysis) data. The structure of the ligand, 4‐bromo‐2‐((E)‐{4‐[(3,4‐dimethylisoxazol‐5‐yl)sulfamoyl]phenyl} iminiomethyl)phenolate was also determined by X‐ray diffraction method. An octahedral geometry was suggested for all the complexes. In order to evaluate the biological activity of the ligands and the effect of metals, the ligands and their metal complexes were screened for in vitro antibacterial, antifungal and cytotoxic activity. The results of these studies revealed that all compounds showed moderate to significant antibacterial activity against one or more bacterial strains and good antifungal activity against various fungal strains. Copyright © 2011 John Wiley & Sons, Ltd.     

Diorganotin(IV) complexes of 2-chloridophenylacetohydroxamic acid as prospective antimicrobials: synthesis,characterization, and biological properties

New diorganotin(IV) complexes [Me₂Sn(2-ClC₆H₄CH₂CONHO)₂] (1) and [n-Bu₂Sn(2-ClC₆H₄CH₂CONHO)₂] (2) have been synthesized by reactions of Me₂SnCl₂ and n-Bu₂SnCl₂ with potassium 2-chloridophenylacetohydroxamate (2-ClPhAHK = 2-ClC₆H₄CH₂CONHOK) in 1:2 molar ratio in MeOH+C₆H₆ solvent medium and characterized by elemental analyses, molar conductivity, molecular weight determinations and spectroscopic techniques (IR, ¹H, ¹³C, and ¹¹⁹Sn NMR) and mass spectrometry. Bonding through carbonyl and hydroxamic oxygens (O,O coordination) and distorted-octahedral geometry around tin is proposed. The electrochemical behavior of 1 and 2 studied by cyclic voltammetry shows quasi-reversible reductions. Thermal behavior of 1 and 2 in N₂ shows decomposition in one step affording SnO as the residue. The in vitro antimicrobial activity assay against pathogenic Gram-negative bacteria viz. Salmonella typhi, Escherichia coli; Gram-positive Bacillus cereus and Staphylococcus aureus and fungi Aspergillus niger and Alternaria alternata by MIC method revealed their significant antimicrobial potential relative to the respective standard Chloramphenicol and Nystatin drugs.     

1,2,4‐Triazole‐based N‐heterocyclic carbene complexes of gold(I): synthesis,characterization and biological activity

Two gold(I) complexes of the (NHC)AuX type bearing a triazole‐based N‐heterocyclic carbene (NHC) ligand (1‐tert‐butyl‐4‐(4‐methylphenyl)‐3‐phenyl‐1H‐1,2,4‐triazol‐4‐ium‐5‐ylidene) and various halide ligands (X = Br, I) were synthesized and characterized in solution using NMR spectroscopy as well as in the solid state using X‐ray diffraction techniques. The cytotoxic properties of both compounds and the precursor, (NHC)AuCl, were screened against a panel of human tumour cell lines including liver cancer (HepG2), cervical cancer (HeLa S3) and leukaemia (CCRF‐CEM, HL‐60) and compared to cisplatin and auranofin. It was found that the activities of the chloro and bromo derivatives were generally superior to that of cisplatin and slightly less effective compared to auranofin, except for HepG2 cells where auranofin was not as effective. In addition, the ability to induce membrane phosphatidyl serine externalization as a hallmark of apoptosis in CCRF‐CEM leukaemic cells was investigated. Copyright © 2016 John Wiley & Sons, Ltd.     

Polymer‐supported metal complexes as antibacterial agents: synthesis,characterization and thermal degradation kinetics

Polymeric metal complexes were prepared using a synthesized novel terpolymer ligand involving anthranilic acid–o‐toluidine–formaldehyde by a polycondensation technique. The synthesized ligand and its metal complexes were characterized using elemental analysis and molar conductivity measurements, and FT‐IR, electronic, electron spin resonance and NMR (¹H and ¹³C) spectral methods. The surface morphology and the nature of the synthesized compounds were examined using scanning electron microscopy and X‐ray diffraction. The thermal stabilities of the ligand and its metal complexes were determined using thermogravimetric analysis (TGA). From the TGA results, various kinetic parameters, i.e. activation energy and order of reaction, and thermodynamic parameters, i.e. entropy change, apparent entropy, frequency factor and free energy change, were determined using the Freeman–Carroll and Sharp–Wentworth methods. In addition, a thermal degradation model was also proposed using the Phadnis–Deshpande method. The thermal stability of the ligand and its metal complexes was found to be appreciably high; in particular, the ligand showed very high stability compared to its metal complexes due to intramolecular hydrogen bonding. Furthermore, the synthesized compounds were subjected to in vitro antibacterial studies with various microorganisms. The results of the studies confirmed that the compounds showed better antibacterial results than a standard antibacterial drug. Copyright © 2014 John Wiley & Sons, Ltd.     

Organometallic based biologically active compounds: synthesis of mono‐ and di‐ethanolamine derived ferrocenes with antibacterial,antifungal and cytotoxic properties

Condensation reactions of 1,1′‐diacetylferrocene with ethanolamine were studied. The obtained compounds were further investigated for their ligation and biological properties with Co(II), Cu(II), Ni(II) and Zn(II) metal ions. The synthesized compounds were characterized by their physical, spectral and analytical properties and screened for their antibacterial properties against pathogenic bacterial strains, e.g. Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus and Salmonella typhi and for antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani and Candida glaberata using the agar‐well diffusion method. All the compounds have shown good antibacterial and antifungal activity, which increased on coordination with the metal ions, thus introducing a potential class of organometallic‐based antibacterial and antifungal agents. Brine shrimp bioassay was also carried out for in vitro cytotoxic properties against Artemia salina. Copyright © 2007 John Wiley & Sons, Ltd.     

Toxicological effects,biological aspects and spectral characterization of organoboron(III) complexes of sulfonamide‐imines

The toxicological effects, biological aspects and spectral characterization of organoboron(III) complexes of sulfonamide‐imines derived by the condensation of salicylaldehyde with different sulfa‐drugs are described. The benzene‐soluble, high‐molecular‐weight complexes have been characterized using a wide range of analytical and spectroscopic techniques, viz. UV, IR, ¹H and ¹¹B NMR. On the basis of these studies, it is inferred that the imines derived from sulfa drugs and salicylaldehyde behave as dibasic tridentate ligands and thus provide a tetrahedral environment around the boron atom. Finally, all these complexes have been screened for their antimicrobial activity against a variety of fungal and bacterial strains and their toxicological effects on male albino rats examined at the dosages employed. Copyright © 2004 John Wiley & Sons, Ltd.     

Syntheses,characterization and biological studies of zinc(II), copper(II) and cobalt(II) complexes with Schiff base ligand derived from 2‐hydroxy‐1‐naphthaldehyde and selenomethionine

Novel zinc(II), copper(II), and cobalt(II) complexes of the Schiff base derived from 2‐hydroxy‐1‐naphthaldehyde and D, L ‐selenomethionine were synthesized and characterized by elemental analysis, IR, electronic spectra, conductance measurements, magnetic measurements and powder XRD. The analytical data showed the composition of the metal complex to be ML(H₂O), where L is the Schiff base ligand and M = Co(II), Cu(II) and Zn(II). IR results confirmed the tridentate binding of the Schiff base ligand involving azomethine nitrogen, naphthol oxygen and carboxylato oxygen atoms. ¹H NMR spectral data of lithium salt of the Schiff base ligand [Li(HL)] and ZnL(H₂O) agreed with the proposed structures. The conductivity values of complexes between 12.50 and 15.45 S cm² mol^?1 in DMF suggested the presence of non‐electrolyte species. The powder XRD studies indicated that Co(II) complex is amorphous, whereas Cu(II) and Zn(II) complexes are crystalline. The results of antibacterial and antifungal screening studies indicated that Li(HL) and its metal complexes are active, but CuL(H₂O) is most active among them. Copyright © 2010 John Wiley & Sons, Ltd.     

Metal-based antibacterial and antifungal sulfonamides: synthesis,characterization, and biological properties

Some furanyl-derived sulfonamides and their cobalt(II), copper(II), nickel(II), and zinc(II) complexes have been synthesized. The structural formulae of the complexes have been inferred by using physico-chemical and spectroscopic methods. The new sulfonamides behave as bidentate ligands in complexation with the metals and an octahedral geometry has been suggested for all these complexes. Both the free sulfonamides and their complexes have been screened for their in vitro antibacterial and antifungal activities against a number of bacteria and fungi. In vitro cytotoxic properties of all the compounds were also studied using brine shrimp bioassay.     

Design,synthesis, characterization and antibacterial properties of copper(II) complexes with chromone‐derived compounds

A new series of six chromone‐derived compounds and their Cu(II) complexes was synthesized and characterized by their physical, spectral and analytical data The elemental analysis data of the complexes agree well with the proposed composition of the compounds, which were found to be dimeric in nature with two hydrazine molecules bridging the two copper atoms through coordination. The ligands and their Cu(II) complexes were screened for their in‐vitro antibacterial activity against four Gram‐negative (Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, Shigella flexneri) and two Gram‐positive (Bacillus subtilis, Staphylococcus aureus) bacterial strains by the agar‐well diffusion method. The ligands were found to exhibit either no or low to moderate activities against one or more of the bacterial species, whereas all the metal complexes exhibited moderate to high activities against different bacterial species. The ligands which were inactive before complexation turned active and less active ones became more active upon coordination with copper ions. Overall, the complexes 7–12 showed comparatively much higher activities than the ligands. Copyright © 2009 John Wiley & Sons, Ltd.     

Synthesis and characterization of biologically active new Schiff bases containing 3‐functionalized 1,2,4‐triazoles and their zinc(II) complexes: crystal structure of 4‐bromo‐2‐[(E)‐(1H‐1,2,4‐triazol‐3‐ylimino)‐ methyl]phenol

Biologically active triazole Schiff bases ( L ¹  L ³ ) derived from the reaction of 3‐amino‐1,2,4‐triazole with chloro‐, bromo‐ and nitro‐ substituted salicylaldehydes and their Zn(II) complexes (1–3) have been synthesized and characterized by their physical, spectral and analytical data. Triazole Schiff bases potentially act as tridentate ligands and coordinate with the Zn(II) metal atom through salicylidene‐O, azomethine‐N and triazole‐N. The complexes have the general formula [M(L‐H)₂], where M = zinc(II) and L = ( L ¹ – L ³ ), and observe an octahedral geometry. The Schiff bases and their Zn(II) complexes have been screened for in‐vitro antibacterial, antifungal and brine shrimp bioassay. The biological activity data show the Zn(II) complexes to be more potent antibacterial and antifungal than the parent simple Schiff bases. Copyright © 2011 John Wiley & Sons, Ltd.     

Synthesis,characterization, metal sorption,and biological activities of organosoluble and thermally stable azoxanthone‐based polyester

The aim of this work was to develop functionalized polyxanthones, poly(azoxanthone‐ester)s (PAXEs), with biological activities and heavy metal sorption abilities. For this purpose, at first, new xanthone‐based diol moiety was synthesized and then used for polymerization with commercial dicarboxylic acids via polycondensation reaction by Vilsmeier adducts. The monomer and all polymers were characterized by Fourier transform infrared (FTIR) and Nuclear magnetic resonance (NMR) spectroscopies, and the physical properties of these PAXEs including solution viscosity, solubility properties, thermal stability, and thermal behavior were studied. The prepared polyesters showed excellent thermal stability and good solubility in polar aprotic solvents. In addition, evaluation of antioxidant activity of the PAXEs by 2,2‐diphenyl‐1‐picrylhydrazyl assay revealed that synthesized polymers have higher antioxidant activity than xanthone nucleus. Also, evaluation of the antibacterial activities of the diol monomer and polymer showed good antibacterial activity against some bacterial strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa). The results showed that these PAXEs can be used in pharmaceutical and food industry (food packaging). Furthermore, these functionalized polyesters were utilized for extraction of environmentally harmful metal cations such as Cr (VI), Co (II), Ni (II), Cu (II), Pb (II), and Cd (II) from aqueous solutions. Copyright © 2015 John Wiley & Sons, Ltd.     

Coordination polymers of glutaraldehyde with glycine metal complexes: synthesis,spectral characterization,and their biological evaluation

Glycine metal complexes were prepared by the reaction of glycine with Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) in 1?:?2 molar ratio. Thereafter their condensation polymerization was done with glutaraldehyde to obtain polymer metal complexes. All the synthesized polymer metal complexes were characterized by elemental analysis, FT-IR, ¹H-NMR, and UV-Vis spectrometry, magnetic susceptibility, and thermogravimetric studies. The analytical data of all the polymers agreed with 1?:?1 molar ratio of metal complex to glutaraldehyde and magnetic moment data suggest that PGG–Mn(II), PGG–Co(II), PGG–Ni(II), and PGG–Cu(II) have an octahedral geometry around the metal atom, whereas the tetrahedral geometry was proposed for PGG–Zn(II) polymer. The PGG–Mn(II) and PGG–Cu(II) showed octahedral geometry. Thermal behavior of the polymer metal complexes was obtained at a heating rate of 10°C?min^?1 under nitrogen atmosphere from 0°C to 800°C. The antimicrobial activities of synthesized polymers were investigated against Streptococcus aureus, Escherichia coli, Bacillus sphaericus, Salmonella sp. (Bacteria), Fusarium oryzae, Candida albicans, and Aspergillus niger (Yeast).     

Synthesis,characterization and in vitro biological activity of cobalt(II), copper(II) and zinc(II) Schiff base complexes derived from salicylaldehyde and D,L‐selenomethionine

New cobalt(II), copper(II) and zinc(II) complexes of Schiff base derived from D,L ‐selenomethionine and salicylaldehyde were synthesized and characterized by elemental analysis, IR, electronic spectra, conductance measurements, magnetic measurements and biological activity. The analytical data showed that the Schiff base ligand acts as tridentate towards divalent metal ions (cobalt, copper, zinc) via the azomethine‐N, carboxylate oxygen and phenolato oxygen by a stoichiometric reaction of M:L (1:1) to form metal complexes [ML(H₂O)], where L is the Schiff base ligand derived from D,L ‐selenomethionine and salicylaldehyde and M = Co(II), Cu(II) and Zn(II). ¹H NMR spectral data of the ligand and Zn(II) complex agree with proposed structures. The conductivity values between 12.87 and 15.63 S cm² mol^?1 in DMF imply the presence of non‐electrolyte species. Antibacterial and antifungal results indicate that the metal complexes are more active than the ligand. Copyright © 2010 John Wiley & Sons, Ltd.     

Synthesis and Characterization of Thiophene‐derived Amido Bis‐nitrogen Mustard and Its Antimicrobial and Anticancer Activities

The thiophene‐derived amido bis‐nitrogen mustard N²,N²,N⁵,N⁵‐tetrakis(2‐chloroethyl)‐3,4‐dimethylthiophene‐2,5‐dicarboxamide was designed and synthesized via five‐step reactions from commercially available 2‐chloroacetonitrile. This target compound was confirmed by ¹H NMR, ¹³C NMR, MS, IR spectra and elemental analyses, and its structure was further characterized by X‐ray single‐crystal analysis. The biological activities for the title compound and some intermediates were evaluated in vitro for their antibacterial, antifungal and cytotoxic activities. The preliminary results showed that the title compound could inhibit efficiently the growth of the tested microorganisms including drug‐resistant bacteria MRSA to some extent. Moreover, the target compound was found to be effective against prostatic carcinoma cell line (PC‐3), breast carcinoma cell line (MCF‐7), colon carcinoma (LoVo) and lung cancer (A549). Especially, it gave selective antitumor efficacy against prostatic carcinoma cell line (PC‐3) at a low dose.     

New metal complexes of sulfonamide: Synthesis,characterization, in‐vitro anticancer,anticholinesterase, antioxidant,and antibacterial studies

In this research work a sulfonamide from tranexamic acid has been synthesized followed by its metal complexation. p‐Bromo benzene sulfonyl chloride was used to synthesize sulfonamide using eco‐friendly atmosphere. The sulfonamide prepared from tranexamic acid has been utilized for the preparation of metal complexes with various metals like Ni, Cu, Co, Mn, Pb, Cd, Cr, Fe, Sn, and Sr. All synthesized compounds were characterized by applying different spectral techniques such as Fourier‐transform infrared (FTIR), mass spectrometry, and X‐ray diffraction (XRD) analysis. The biological activities such as radical scavenging activity, enzyme inhibition, antifungal, antibacterial, and anticancer were performed. It was concluded from the results that compounds showed moderate to good activity. Cu complex of sulfonamide showed the highest antioxidant potential (87.69 ± 1.8% with IC₅₀ 137 ± 1.0 μg) while Cr complex depicted the highest activity against both enzymes; AChE (73.51 ± 1.7% with IC₅₀ 165 ± 1.1 μg) and BChE (70.05 ± 1.3% with IC₅₀ 152 ± 1.8 μg). Mn complex showed good results against six bacterial strains comparable with standard drug. Cr complex depicted highest anticancer activity against MCF7 and human corneal epithelial cell (HCEC) cell lines 45.73% and 25.40%, respectively. These results concluded that metal complexes of sulfonamide may be good induction in the future for medical purposes.     

Terpyridine‐substituted,fluorescent polymers and their chelation with zinc ion: The ligand‐to‐metal ratio and optical properties

Soluble, fluorescent, terpyridine‐substituted, conjugated polymers were prepared and characterized. The polymer chains included a defined oligo(phenylenevinylene) fragment, on which the terpyridine‐functional group was attached. The polymers were blue‐fluorescent with emission peaks at 400–427 nm in tetrahydrofuran solutions. Upon chelation with the Zn(II) cation, the emission maxima were shifted to a longer wavelength by as much as 113 to 506–526 nm. A model compound was also prepared to aid the structural characterization. The ratio of terpyridine to Zn²⁺ in the polymer complex was found to be 1:1 on the basis of spectroscopic evidence, which included mass spectrometry, ¹H NMR, and Job titration. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 2338–2345, 2006