Synthesis of nitrogen-containing monoterpenoids with antibacterial activity

Abstract

Incorporation of the Beckmann rearrangement into the presented research resulted in the formation of nitrogen-containing terpenoid derivatives originating from naturally occurring compounds. Both starting monoterpenes and obtained derivatives were subjected to estimation of their antibacterial potential. In the presented study, Staphylococcus aureus was the most sensitive to examined compounds. The Minimal Inhibitory Concentration (MIC) experiments performed on S. aureus demonstrated that the (−)-menthone oxime (−)-8 and (+)-pulegone oxime (+)-13 had the best antibacterial activity among the tested derivatives and starting compounds. Their MIC90 value was 100 µg/mL. The obtained derivatives were also evaluated for their inhibitory activity against bacterial urease. Among the tested compounds, three active inhibitors were found – oxime 14 and lactams (−)-15 and 16 limited the activity of Sporosarcina pasteurii urease with Ki values of 174.3 µM, 43.0 µM and 4.6 µM, respectively. To our knowledge, derivative 16 is the most active antiureolytic lactam described to date.