Efficient synthesis and antibacterial activity of N-(o-benzyloxy/hydroxyphenyl) benzohydroxamic acids

Abstract

A modified one-pot two-step method has been developed to synthesize N-(o-benzyloxyphenyl) benzohydroxamic acids from o-benzyloxy nitrobenzene in good to excellent yields. The synthesized N-(o-benzyloxyphenyl) benzohydroxamic acids were subjected to benzyl deprotection using Pd-C catalyst under H₂ gas atmosphere to afford corresponding N-(o-hydroxyphenyl) benzohydroxamic acids. All the synthesized N-(o-benzyloxy/ hydroxyphenyl) benzohydroxamic acids were characterized by ¹H-, ¹³C NMR, FT-IR, UV-Vis., HRMS (ESI) and the structure of the compound 5d was further confirmed by analyzing its X-ray data. The synthesized novel N-(o-benzyloxy/ hydroxyphenyl) benzohydroxamic acids were screened for antibacterial activity against the bacterium Escherichia coli by the serial broth microdilution method using microplate alamar blue assay (MABA). The synthesized derivatives showed significant activity against E. coli.

Graphical Abstract

Keywords:

• Benzohydroxamic acids
• N-phenylhydroxyl amine
• one-pot synthesis
• antibacterial activity

Acknowledgements

We are thankful to CIF-USIC, University of Delhi, for providing the NMR spectral and HRMS recording facility. RT would like to thanks the University Grants Commission (UGC), New Delhi for providing the Junior/ Senior Research Fellowship under RGNF scheme.