Novel bisstyryl derivatives of bakuchiol: Targeting oral cavity pathogens

Novel bisstyryl derivatives of bakuchiol using Heck coupling reaction as the key step were synthesized and screened against a panel of six oral cavity pathogens for their antimicrobial activity. Four compounds (9–12) showed two to fourfold and four to eightfold better activity (MIC 0.25–16 μg/ml) than bakuchiol and triclosan respectively. These compounds effectively inhibit the biofilm formation of single and multiple species at 2 – 8 × MICs. 4- and 4′-Hydroxy/methoxy styryl moieties of the bakuchiol derivatives play a pivotal role towards the activity as established in the SAR studies. Mechanism of action studies revealed microbial membrane structure disruption as the probable mode of action of these compounds.

Graphical abstractNovel bisstyryls derived via Heck coupling reaction of (S)-bakuchiol as oral antimicrobial agents along with their mode of action and SAR is described.Figure optionsDownload full-size imageDownload as PowerPoint slide