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Synthesis, characterization and antimicrobial activity of salicylaldehyde benzenesulfonylhydrazone (Hsalbsmh)and its Nickel(II), Palladium(II), Platinum(II), Copper(II), Cobalt(II) complexes

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Abstract

In this study Benzenesulfonicacid-1-methylhydrazide (bsmh) derivatives such as salicylaldehyde benzenesulfonylhydrazone (Hsalbsmh) and its Ni(II), Pd(II), Pt(II), Cu(II), Co(II) complexes were synthesized for the first time. The structure of these complexes was investigated by using elemental analyses, the FT-IR, LC–MS and UV–VIS spectrophotometric methods, magnetic susceptibility and conductivity measurement techniques. The complexes were found to have general compositions [ML2]. Using disk diffusion methods all the synthesized complexes were evaluated in vitro as antimicrobial agents against representative strains of gram-positive (Staphylococcus aureus ATCC 25923, Bacillus cereus ATCC 11778, Enterococcus faecalis ATCC 29212, Bacillus subtilis ATCC 6633, Staphylococcus epidermidis ATCC 12228, Enterobacter aerogenes ATCC 13048) and gram-negative bacteria (Pseudomonas fluorescens ATCC 49838, Klebsiella pneumoniae ATCC 13883, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853) and as an antifungal agent against Candida albicans (ATCC 90028). All the bacteria and fungus studied were screened against some antibiotics to compare with our chemical zone diameters.

Graphical abstract

We obtained a new ligand (Hsalbsmh) and its five metal complexes [Ni(salbsmh)2, Pd(salbsmh)2, Pt(salbsmh)2, Cu(salbsmh)2 and Co(salbsmh)2] and characterized their structure by FT-IR, Elemental Analysis, UV–VIS, Magnetic Susceptibility and LC/MS techniques and investigated their antibacterial activities.

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Highlights

► Benzenesulfonicacid-1-methylhydrazide (bsmh) + Salycylaldehyde  salycylaldehyde benzenesulfonylhydrazone (Hsalbsmh). ► Hsalbsmh + MCl2  M(salbsmh)2 (M: Ni(II), Pd(II), Pt(II), Cu(II), Co(II)). ► Characterization Hsalbsmh and its complexes. ► Antimicrobial activities of Hsalbsmh and its complexes.

Introduction

The sulfonamide single bondSO2NHsingle bondgroup occurs in numerous biologically active compounds which include antimicrobial drugs, saluretics, carbonic anhydrase inhibitors, insulin-releasing sulfonamides, antithyroid agents, antitumor drugs and in a number of other biological activities. Furthermore, low cost and low toxicity are their principle advantages [1], [2], [3], [4], [5], [6], [7], [8], [9], [10], [11], [12], [13], [14], [15].

Methanesulfonamide derivatives possess DNA-binding ability, show cytostatic effects, and some of them, like Amsacrine, are used in cancer chemotherapy treatment [16], [17], [18], [19]. Some sulfonylhydrazines are known to have antineoplastic effects which prevent malign cells from growing and spreading [20]. Imidosulfonylhydrazones have antibacterial and antinociceptive properties [21]. Acidic sulfonyl hydrazone derivatives have analgesic and anti-inflammatory properties [22]. Benzaldehyde arylsulfonylhydrazones possess antineoplastic activity against human stomach cancer SGC 7901 cells [23]. 4-substituted benzenesulfonylhydrazone has been found to have antibacterial activity [24].

A further extension of this area was made by the formation of the silver (I) complex of sulfonylamide which emphasized the role of metals in enhancing biological activity [25]. The transition metal complexes of hydrazides and sulfonamides also have applications in chemotherapy. The synergetic action of sulfonamides with trimethoprim has brought about an enormous resurgence of sulfonamide usage in many areas over the past decade.

This prompted us to synthesize a series of novel symmetric aromatic sulfonamide complexes. We obtained a series of new sulfonamide complexes (1–5) and characterized their structure by FT-IR, LC/MS, UV–VIS, magnetic susceptibility and elemental analysis techniques. We also studied their antibacterial activities against gram-positive and gram-negative bacteria and as an antifungal agent using the disk diffusion method. All of the bacteria and fungus studied were screened against standard antibiotics to compare them with our chemical zone diameters.

The structural formula of the series of aromatic sulfonamide complexes (1–5) is given in Fig. 1.

Section snippets

Physical measurements

The infrared spectra of the compounds as KBr-disks were recorded in the range of 4000–400 cm 1 with a Mattson 1000 FT-IR spectrometer. LC/MS-APC1 was recorded on an AGILENT 1100. UV–VIS spectra were recorded on a UNİCAM-UV 2–100 spectrophotometer. The melting point was recorded on an Opti MELT 3 hot stage apparatus. TLC was conducted on 0.25 mm silica gel plates (60 F254, Merck). Visualization was made with ultraviolet light. The molar magnetic susceptibilities were measured on powdered samples

Results and discussion

The results of elementary analysis showed 1:2 (metal/ligand) stoichiometry for all the complexes. The analytical results were in good agreement with those required by the general formula [ML2]. The molar conductivity (Λm) of the 10 3 M solutions of the complexes in DMSO at 25 °C was measured and all complexes were found to be of non-electrolytic nature.

The Hsalbsmh ligand and its complexes which we studied have not been previously reported in the literature.

Conclusions

In conclusion, a series of novel aromatic sulfonamide complexes were synthesized and their antimicrobial activities were evaluated. All compounds demonstrated potent inhibition against all the strains tested. From the spectroscopic characterization, it was concluded that sulfonylhydrazones act as bidentate ligands, coordinating through single bondCdouble bondN and phenolic single bondOH via deprotonation. Further research in this area is in progress at our laboratory. Consequently, these compounds may be recommended for

Acknowledgments

The authors are grateful to the TUBITAK Research Foundation for its financial support under project number 104 T 390.

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