Synthesis, characterization and investigation of antibacterial and antifungal activities of novel 1,3-butadiene compounds

Abstract

The nitro group–substituted perhalogenobuta-1,3-diene (1) is important synthetic precursor in the synthesis of different heterocycles groups with high biological activity. Firstly, new N,S-substituted-perhalonitro-1,3-butadiene compounds were synthesized by the reactions of various amino or thiol containing nucleophiles with 1. The structures of all new compounds have been identified by using spectroscopic techniques (FT-IR, ¹H-NMR, ¹³C-NMR, MS and microanalysis). Secondly, their antimicrobial properties were tested as potential antibacterial and antifungal agents. Antimicrobial activity of synthesized N,S-substituted perhalonitrobutadienes 4a–j and 5a–d was evaluated against Escherichia coli B-906, Staphylococcus aureus 209-P, and Mycobacterium luteum B-917 bacteria and Candida tenuis VKM Y-70 and Aspergillus niger F-1119 fungi and the compounds 4c, 4d, 5a and 5b with high antifungal action against test-culture Aspergillus niger at MIC values 0.9–1.9 μg/cm³ were identified as the most potent.

Graphical Abstract

Keywords:

• Antifungal activity
• antibacterial activity
• heterocyclic ring–substituted 1,3-butadiene
• piperazine
• thiol

Additional information

Funding

We gratefully thank the Research Fund of Istanbul University-Cerrahpasa for financial support of this work [Project Numbers: FYL-2016-20351, FBA-2019-30472, FBA-2019-32783].