Design, synthesis, molecular docking, density functional theory and antimicrobial studies of some novel benzoxazole derivatives as structural bioisosteres of nucleotides

Abstract

A series of some novel 2-(p-tert-butylphenyl)-5-(3-substituted-propionamido)benzoxazole derivatives have been designed, synthesized, evaluated for antimicrobial activity and have performed molecular docking studies against penicillin-binding protein 4 (PBP4) and active and allosteric site of PBP2a; were calculated some theoretical quantum parameters and absorption, distribution, metabolism and excretion (ADME) descriptors. B9 acted at minimum inhibitory concentration (MIC) = 8 µg/mL against S. aureus, E. faecalis and their drug-resistant isolates and also formed with GLU145 (1.74 Å) and ILE144 (1.89 Å) two hydrogen bonds at allosteric site of PBP2a with Glide emodel score: −42.168. ΔE of compound B9 had moderate value of all compounds with 0.14742.

Communicated by Ramaswamy H. Sarma

Keywords:

• ADME prediction
• antimicrobial activity
• benzoxazole
• DFT
• molecular docking

Acknowledgements

The Central Laboratory of the Faculty of Pharmacy of Ankara University and Erciyes University Technology and Research Center (TAUM) supported the acquisition of the NMR and mass spectra and elemental analyses in this work.

Disclosure statement

No potential conflict of interest was reported by the authors.