Synthesis, biological evaluation and molecular docking of 2-phenyl-benzo[d]oxazole-7-carboxamide derivatives as potential Staphylococcus aureus Sortase A inhibitors

Yong Zhang, Jian Bao, Xin Xian Deng, Wan He, Jia Jun Fan, Fa Qin Jiang*, Lei Fu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)


A series of novel 2-phenyl-benzo[d]oxazole-7-carboxamide derivatives were designed, synthesized and evaluated for their in vitro inhibitory activities against Staphylococcus aureus Sortase A with known Sortase A inhibitor pHMB as positive compound (IC50 = 130 μM). Most compounds exhibited excellent inhibitory activity (IC50 = 19.8–184.2 μM). Structure–activity relationship studies demonstrated that substitution at 7-position and 2-position of benzoxazole had great influence on the activities. Specifically, the substituent at 7-position is indispensable for inhibitory activity. The molecular docking studies revealed the i-butyl amide group went towards the β6/β7 loop-β8 substructure of the protein and the benzoxazole core lied in a hydrophobic pocket composed of Ala118, Val166, Val168, Val169 and Ile182, shaping the whole molecule into a L-shape mode to be recognized by Sortase A.

Original languageEnglish
Pages (from-to)4081-4085
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Issue number16
Publication statusPublished - 2016
Externally publishedYes


  • Anti-infective
  • Benzo[d]oxazole
  • Sortase A

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