Design, synthesis and <i>in‐vitro</i> evaluation of new furan‐substituted thiadiazolyl hydrazone derivatives as promising antimicrobial agents
Mirna T. Helmy, Farid M. Sroor, Abdelmageed M. Othman, Hamdi M. Hassaneen, Fatma M. Saleh, Mohamed A. Mohamed Teleb
Abstract
Abstract Seventeen new furan‐substituted thiadiazolyl hydrazone derivatives bearing 4‐nitrophenyl moiety were designed, synthesized and tested for their in vitro antimicrobial activity. Reaction of N ‐(4‐nitrophenyl)‐ C ‐(furan‐2‐yl)methanohydrazonoyl chloride 1 with 2‐((methylthio)carbonthioyl)hydrazine derivatives 3 , 7 , 8 and 11–13 in absolute ethanol in the presence of triethylamine at room temperature afforded the corresponding 1,3,4‐thiadiazole derivatives 6 , 9 , 10 and 14–16 . Refluxing of 1‐(3‐(furan‐2‐yl)‐5‐methyl‐1‐(4‐nitrophenyl)‐1 H ‐pyrazol‐4‐yl)ethan‐1‐one 17 with methyl hydrazinecarbodithioate 18 in absolute ethanol in the presence of few drops of hydrochloric acid yielded methyl‐2‐(1‐(3‐(furan‐2‐yl)‐5‐methyl‐1‐(4‐nitrophenyl)‐1 H ‐pyrazol‐4‐yl)ethylidene)hydrazine‐1‐carbodithioate 19 . The compound 19 was reacted with hydrazonoyl halides 20a‐e in absolute ethanol in the presence of triethylamine afforded the corresponding 1,3,4‐thiadiazoles 24a‐e . The specified compounds were tested for antimicrobial activity against selected model microorganisms. Antimicrobial studies revealed that compounds 6c , 6d and 15 against E. coli , compounds 6b , 6c , 10 , 14 , 15 , 24b and 24c against B. mycoides , and compounds 14 , 16 , 19 and 24d against C. albicans outperformed other developed compounds in terms of antimicrobial activity.