Synthesis of novel menthol derivatives containing 1,2,3-triazole group and their in vitro antibacterial activities

New N-substituted alpha-aminonitrile derivatives from menthol were synthesized by consecutive succinic ester formation, propargylation, 1,3-dipolar Huisgen cycloaddition and Strecker reaction. The structures of the synthesized compounds were confirmed by diverse spectroscopic techniques including 1H-NMR, 13C-NMR, ESI-MS and IR. The novel synthesized compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus as Gram-positive and Escherichia coli as Gram-negative bacteria. These compounds demonstrated a strong inhibitory effect against S. aureus with the minimum inhibitory concentration (MIC) values ranged from 32-128 mu g mL-1. Derivatives 6a2, 6b1, 6b4 and 6b5 with a MIC value of 32 mu g mL-1 exhibited the best inhibitory effects.

Automated summary

New N-substituted alpha-aminonitrile derivatives were synthesized from menthol via consecutive succinic ester formation, propargylation, 1,3-dipolar Huisgen cycloaddition, and Strecker reaction. The structures of the synthesized compounds were confirmed using spectroscopic techniques. These novel compounds showed strong inhibitory effects against Staphylococcus aureus and Escherichia coli, with the best inhibitory effects exhibited by derivatives 6a2, 6b1, 6b4, and 6b5.