Synthesis, Antibacterial Activity and Molecular Modelling of Benzyl Acetate Derivatives

Abstract

Benzyl alcohol derivatives are known for their antibacterial efficacy. In this work five known benzyl acetate derivatives were synthesized by the acetylation of their corresponding benzyl alcohol derivatives and their structures confirmed using 1H, 13C NMR and FTIR spectroscopic techniques. The synthesized compounds were tested for antibacterial activity against Staphylococcus aureus and Shigella spp using disc diffusion method. Also the activity of amoxicillin disc (0.5 g/L ) was measured as a positive control. Furthermore, the drug-likeness as well as the interactions of the compounds against the active site of E. coli carbonic anhydrase which share >98% similarity to that of S. spp were studied using molecular modelling method. The antibacterial activity showed that all the five compounds 3a-e inhibited the two organisms at 100 µg/ml compared to the positive control. The largest inhibition zones of Staphylococcus aureus and Shigella spp were found to be 16.5 mm and 17.5 mm for compound 3d and 3e, respectively. Molecular modelling predicted the compounds to be water soluble, highly absorbed through GI tract, not Pgp substrates and not CYP3A4 inhibitors. Molecular docking studies showed that the compounds showed affinity to E. coli carbonic anhydrase active site, blocking access to the Zn2+ cofactor.