سنتز مشتقات هیدرازیدی از ساخارین و بررسی فعالیت شلاته‌ کنندگی آن‌ها

Background and purpose: Zinc (Zn), copper (Cu) and iron (Fe) are essential minerals required for a variety of biomolecules to maintain the normal structure, function, and proliferation of cells. Abnormal metabolism of heavy metals can lead to several chronic pathogenesis. In this study, two new saccharin hydrazide derivatives were synthesized and their chelatory activities were evaluated. Materials and methods: Acetic acid ethyl ester and propionic acid ethyl ester derivatives of saccharin were synthesized by the reaction of the starting materials (saccharin) with ethyl bromoacetate and ethyl bromopropionate under the reflux condition and using the dimethylformamide (DMF) as solvent. Ester compounds were stirred with hydrazine hydrate in ethanol and then the products were isolated. The desired hydrazide compounds were purified by thin layer chromatoghraphy. The ultraviolet (UV) spectra of hydrazide products in the absence and presence of ethylenediaminetetraacetic acid (EDTA) were obtained in order to the analysis of chelating activity with Fe2+ and Fe3+, Zn, Cu and alluminium (Al). All products were determined by analytical methods [nuclear magnetic resonance (NMR) and infrared (IR) spectroscopy]. Results: Crystallization method was used for purification of compounds. The reactions’ yields obtained 44 to 46%. Compounds showed good chelatory activites against Fe3+. In presence of EDTA, the reaction of complex production returned back to previous state which suggested less chelating power of the compound. Conclusion: Overall, saccharin derivatives had the ability to chelate Fe3+ more efficient than that of other metals.