Triazenes and antibacterial activity

Abstract

Fifteen triazenes compounds were studied concerning their antibacterial activity by broth microdilution method. Minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) was determined with E. coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, Acinetobacter baumannii, Acinetobacter lwoffii, Ralstonia pickettii, Bordetella bronchiseptica, Micrococcus sp., Enterococcus sp., Staphylococcus epidermidis, Staphylococcus saprophyticus, Streptococcus agalactiae, Bacillus cereus, Corynebacterium sp., Rhodococcus sp., Salmonella sp., Serratia marcescens, Morganella morganii, Enterobacter cloacae, Shigella flexneri, Shigella sonnei, Shigella sp., Klebsiella pneumoniae, ESBL Klebsiella oxytoca 14, ESBL Klebsiella pneumoniae 23, ESBL Klebsiella pneumoniae 24, ESBL Klebsiella pneumoniae 25, ESBL Escherichia coli 26, ESBL Klebsiella pneumoniae 27, ESBL Klebsiella pneumoniae 31, ESBL Escherichia coli 32, ESBL Klebsiella pneumoniae 37 e ESBL Escherichia coli 38. The highest effect was evidenced by the compound 1-methyl-3-(p-carboxyphenyl)triazene 1-oxide (2) against Streptococcus agalactiae (MIC = 16 µg/mL and MBC = 32 µg/mL). The compounds 1-phenyl-3-(4-nitrophenyl)triazene-1-oxide (9), 1-(4-nitrophenyl)-3-(4-carboxyphenyl)triazene (10) e 1-(4-acethyl amine phenyl)-3-(4-carboxyphenyl)triazene (11) presented MIC between 32 and 64 µg/mL against S. edipermidis, S. saprophyticus, Rhodococcus sp. and E. cloacae. The compounds 1-methyl-3-phenyltriazene-1-oxide (1) , bis-1,3-(4-acethyl oxime)triazene (3), bis-1,3 (4-acethyl phenyl)triazene (4), 1-(2-fluorophenyl)-3-(4-acethylphenyl)triazene (5), 1,3-(3-hydroxy-diphenyltriazenide)(piridil)(bis-oxo-vanadium) (12), 1-(3-nitrophenyl)-3-phenyltriazene (14), 1-(4-nitrophenyl)-3-benzyltriazene (15) presented MIC of the 128 µg/mL against S. aureus ATCC 25923, P. aeruginosa ATCC 27853, A. lwoffii, Micrococcus sp., S. epidermidis, S. saprophyticus, Corynebacterirum sp., E. cloacae, S. flenneri e S. sonnei. The compounds 1-phenyl-3-(4-acethylphenyl)triazene (6), 1,3-bis-(4-ethoxycarbonylphenyl) triazene (7), and 3-(4-carboxylatephenyl)-1-methyltriazene 1-oxide of potassium tetrahydrate (13) presented MICs equals or highest than 128 µg/mL. The results have demonstrated the potential biological activity of these compounds against Gram-positive and Gram-negative bacteria.