Chiral (S)-BINOL-phosphates: Design, synthesis and their antibacterial and α-glucosidase inhibition studies

Abstract

A new series of chiral (S)-BINOL-derived phosphoric acid derivatives (8a-k) with 3,3′-disubstitution were successfully synthesized under microwave irradiation, yielding high product quantities within a short reaction time. The antibacterial and α-glucosidase inhibitory properties of these compounds were evaluated. Notably, compound 8b exhibited remarkable antibacterial efficacy against B. subtilis, S. aureus, S. epidermidis, P. aeruginosa, and K. pneumoniae, with a MIC value of 1.17 g mL−1. Furthermore, the electron-withdrawing nitro group-containing derivative, 8d displayed potent antibacterial activity (MIC = 1.17 g mL−1) against B. subtilis, S. epidermidis, and E. coli. Among the synthesized compounds, compound 8b, containing chloro substitutions at the 3,5-positions of the phenyl groups in (S)-3,3′-disubstituted BINOL, demonstrated the most noteworthy α-glucosidase inhibitory activity with IC50 value of 2.067 ± 0.017 M.