Design, Synthesis, and Antimicrobial Evaluation of N-(۲,۵-Dihydro-pyrimidine-۲-yl)-۴-methyl-benzenesulfonamide and its silver complex

BACKGROUND AND OBJECTIVESSulfonamides with biological activity are known as sulfa drugs (with -S(=O)۲-NR۲ functional group) and treat various bacterial, fungal, and viral infections. The mechanism of effectiveness of sulfonamides is the structural similarity between sulfonamide and ρ-aminobenzoic acid (PABA). The present study aims to Compare the Antibacterial activities of N-(۲,۵-Dihydro-pyrimidine-۲-yl)-۴-methyl-benzenesulfonamide (L) and its silver complex (C۱) by determining MIC.MATERIALS AND METHODSAll purchased chemicals were of reagent grade and used without further purification. N-(۲,۵-Dihydro-pyrimidine-۲-yl)-۴-methyl-benzenesulfonamide (L) was synthesized from the reaction of ۲-Amino Pyrimidine and ۴-methyl benzenesulfonyl chloride in dichloromethane solvent one-pot synthesis and under reflux conditions (at a temperature of ۶۰˚C) for ۸ hours, without a catalyst. The progress of the reaction was followed by thin-layer chromatography (TLC). Then the precipitate was washed with ethyl acetate and distilled water at a ratio of ۱:۲; methanol/Acetonitrile recrystallized the precipitate. ۸ mmol of N-(۲,۵-Dihydro-pyrimidine-۲-yl)-۴-methyl-benzenesulfonamide (L) was dissolved in Deuterium-depleted water and ethanol (۲۰ mL, ۱:۱). ۸ mmol of Silver nitrate was added into the solution of ligand and stirred the reaction mixtures for ۲۴ hours at room temperature. The precipitates were filtered and kept at ۴˚C until the day of use. Antibacterial effects of the synthesized sulfonamide compounds, the minimum inhibitory concentration of bacterial growth (MIC) was determined based on the CLSI reference protocol and by microdilution method in a ۹۶-well microplate using Mueller Hinton Broth. The microbial strains required in this study were purchased from the Iranian Biological Resource Center, including Escherichia coli (IBRC-M ۱۰۸۷۱), Pseudomonas aeruginosa (IBRC- M ۱۰۲۰۵), Staphylococcus aureus (IBRC- M ۱۰۶۹۰), Bacillus subtilis (IBRC- M ۱۰۷۴۲).RESULTS AND DISCUSSIONN-(۲,۵-Dihydro-pyrimidine-۲-yl)-۴-methyl-benzenesulfonamide and its silver complex were characterized with FT-IR, ۱HNMR, and Single Crystal Crystallography. The order of activities against E.coli, P.aeruginosa, S.aureus, and B.subtilis with MIC of L was ۱.۲۵, ۰.۳۱۲, ۱.۲۵, and ۱۰ mg/ml, and for C۱, ۰.۰۷۸, ۰.۰۷۸, ۰.۰۷۸, and ۲.۵ mg/ml, respectively.CONCLUSIONIt was shown that L and C۱ have moderate to significant activity against all bacteria types and have more inhibitory effects on Gram-negative than Gram-positive bacteria.

کلیدواژه ها:

Sulfonamide ، N-(۲ ، ۵-Dihydro-pyrimidine-۲-yl)-۴-methyl-benzenesulfonamide ، Antimicrobial Evaluation