Synthesis using microwave irradiation and antibacterial evaluation of new N,O-acetals and N,S-acetals derived from 2-amino-1,4-naphthoquinones

This paper describes a novel series of N,O-acetals and N,S-acetals (7a–o) derived from 2-amino-1,4-naphthoquinones that were synthesized and evaluated as potential antimicrobial agents. These compounds were obtained in good yields using microwave irradiation, and several of them showed promising antibacterial profiles. Three of our biologically active 2-amino-1,4-naphthoquinone N,O-acetals and N,S-acetals tested against hospital bacterial strains were identified as potential lead compounds. Characterization of all compounds was performed using one-dimensional NMR techniques (1H, 13C-APT), IR spectra, elemental analyses and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS).

Graphical abstractThis paper describes a novel series of N,O-acetals and N,S-acetals (7a–o) derived from 2-amino-1,4-naphthoquinones that were synthesized and evaluated as potential antimicrobial agents. These compounds were obtained in good yields using microwave irradiation, and several of them showed promising antibacterial profiles.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► We synthesized a series of fifteen naphthoquinones. ► Two naphthoquinones were used as the starting material. ► We evaluated them as antibacterial activity. ► Three compounds showed a reasonable inhibition against hospital bacterial strains.