Design, Synthesis, and Antimicrobial Evaluation of ۱-tosyl-۱H,۱,۲,۴-triazol-۵-amine

BACKGROUND AND OBJECTIVESToday, diseases caused by bacteria and fungi adversely affect society's health. Antibiotics are the most common drugs used worldwide and an essential part of treatment, and they are considered critical drugs in the treatment and prevention of Infectious Diseases. The present study aims to synthesize new N-heteroaryl sulfonamide compounds to control and eliminate bacterial and fungal species.MATERIALS AND METHODSAll purchased chemicals were of reagent grade and used without further purification. ۱-tosyl- ۱H,۱,۲,۴-triazol-۵-amine (L) was synthesized from the reaction of ۳-amino-۱,۲,۴-triazole and ۴- methyl benzene sulfonyl chloride in dichloromethane solvent one-pot synthesis and under reflux conditions (at a temperature of ۶۰°C) for ۸ hours, without a catalyst. Then the precipitate was washed with ethyl acetate and distilled water at a ratio of ۱:۲; methanol/Acetonitrile recrystallized the precipitate. FT-IR, ۱H-NMR, characterized the prepared L. Single X-ray crystal structure analysis determined molecular and crystal structures. The antimicrobial activity includes the evaluation of the antibacterial effects of the L, including the evaluation of the antibacterial activity of Disk Diffusion (by the Kirby-Bauer method) by measuring the diameter of the growth inhibition zone. The microbial strains required from the Iranian Biological Resource Center Was purchased. The bacterial suspension was prepared equaled ۰.۵ McFarland in the disk diffusion method. Incubation was done at ۳۷°C for ۲۴ hours. This study used the disk containing gentamicin (۱۰μg) as a positive control, and the disk containing dimethyl sulfoxide as a negative control.RESULTS AND DISCUSSION۱-tosyl-۱H,۱,۲,۴-triazol-۵-amine (C۱۸H۲۰N۸S۲O۴), IR (KBr) (ʋ, cm-۱): ۳۴۰۰ (NH۲), ۳۱۱۰ (C-H aromatic), ۱۶۲۸ (-C=N), ۱۵۰۴ (C=C aromatic), ۱۳۶۸-۱۲۰۷ (-N-S(=O)۲). The antibacterial activity against E.coli, P.aeruginosa, S.aureus, and B.subtilis with the diameter of the growth inhibition zone of L was ۱۵.۹±۰.۲, ۱۷±۰.۲۴, ۱۸.۴±۰.۱۷, and ۱۰±۰.۲۲, respectively. The results were compared with those of Gentamycin. It was observed that the L showed moderate to significant activity against all Gram-negative and Gram-positive bacteria.CONCLUSIONBased on the data obtained in this test, L showed more inhibitory effect on Gram-negative bacteria (E.Coli, P.aeruginosa) than Gram-positive bacteria (S.aureus, B.Subtilis).

کلیدواژه ها:

Sulfonamide ، ۱-tosyl-۱H ، ۱ ، ۲ ، ۴-triazol-۵-amine ، Antimicrobial Evaluation