Synthesis of Functionalized <i>N</i>-(4-Bromophenyl)furan-2-carboxamides via Suzuki-Miyaura Cross-Coupling: Anti-Bacterial Activities against Clinically Isolated Drug Resistant <i>A. baumannii</i>, <i>K. pneumoniae</i>, <i>E. cloacae</i> and MRSA and Its Validation via a Computational Approach

• Main Authors: Ayesha Siddiqa (Author), Muhammad Zubair (Author), Muhammad Bilal (Author), Nasir Rasool (Author), Muhammad Usman Qamar (Author), Aqsa Khalid (Author), Gulraiz Ahmad (Author), Muhammad Imran (Author), Sajid Mahmood (Author), Ghulam Abbas Ashraf (Author)
• Format: Book
• Published: MDPI AG, 2022-07-01T00:00:00Z.
• Subjects: article
• Online Access: Connect to this object online.

Summary

<i>N</i>-(4-bromophenyl)furan-2-carboxamide (<b>3</b>) was synthesized by the reaction furan-2-carbonyl chloride (<b>1</b>) and 4-bromoaniline (<b>2</b>) in the presence of Et₃N in excellent yields of 94%. The carboxamide (<b>3</b>) was arylated by employing triphenylphosphine palladium as a catalyst and K₃PO₄ as a base to afford <i>N</i>-(4-bromophenyl)furan-2-carboxamide analogues (<b>5a-i</b>) in moderate to good yields (43-83%). Furthermore, we investigated the in vitro anti-bacterial activities of the respective compounds against clinically isolated drug-resistant bacteria <i>A. baumannii</i>, <i>K. pneumoniae</i>, <i>E. cloacae</i> and <i>S. aureus</i>. The molecule (<b>3</b>) was found to be the most effective activity against these bacteria, particularly NDM-positive bacteria <i>A. baumannii</i> as compared to various commercially available drugs. Docking studies and MD simulations further validated it, expressing the active site and molecular interaction stability.

Item Description

10.3390/ph15070841
1424-8247