Synthesis, Characterization and Antibacterial Assays of Novel N,N1‐Disubstituted 2,2′‐Dithiodianiline Derivatives

• Published in: ChemistrySelect (Weinheim) 2023-07, Vol.8 (25), p.n/a
• Main Authors: Skrickus, Karolis, Šiugždaitė, Jūratė, Lelešius, Raimundas, Anusevičius, Kazimieras, Grybaitė, Birutė, Vaickelionienė, Rita, Mickevičius, Vytautas
• Format: Article
• Language: English
• Subjects: antibacterial activity; azole; disulfur bridge; hydrazone; β-amino acid
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202300332

A series of novel 1,2‐bissubstituted disulfanes bearing beta‐amino acid, dihydropyrimidine‐2,4‐(1H,3H)‐dione, hydrazide, hydrazone and azole moieties were synthesized. The antibacterial activity was evaluated by determining minimum inhibition (by broth microdilution) and minimum bactericidal (by growth on agar) concentrations. The assessment revealed that MIC values for L. monocytogenes varied between 3.9 and 62.5 μg/mL as well as for S. aureus ranged between 7.8 and 250 μg/mL, with the exception of one compound with much weaker MIC of 500 μg/mL. The MBC values for L. monocytogenes have been found to be of 7.8–250 μg/mL, while S. aureus demonstrated the higher resistance and MBCs varied in the range of 7.8–500 μg/mL. The determined MBC/MIC ratios showed that eleven compounds were classified bactericidal agents for all tested bacteria. The family of 2,2′‐dithiodianilines are reported in the scientific literature as very important compounds with wide‐ranging biological activities. Using diamine a series of new disulfide‐bridged bisderivatives were synthesized and their antibacterial properties were investigated. The antibacterial susceptibility test confirmed all these derivatives to possess an inhibitory effect on the growth of both Gram‐negative bacteria species but only 14 of them inhibited both Gram‐positive ones.