Synthesis and structure-activity relationship of 1-[(E)-3-phenyl-2-propenyl] piperazine derivatives as suitable antibacterial agents with mild hemolysis

Document Type : Article

Authors

1 Department of Chemistry Government College University Lahore

2 Department of Chemistry, Government College University Lahore

3 Department of Chemistry, Government College University, Lahore-54000, Pakistan

4 Department of Chemistry Government College University Lahore

5 Faculty of Pharmacy and Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

6 Department of Biochemistry, University of Agriculture, Faisalabad-38040, Pakistan

Abstract

A new series of 1-[(E)-3-phenyl-2-propenyl]piperazine derivatives (5a-m) as antibacterial agents was designed and synthesized. The synthetic strategy was initiated by coupling different anilines (1a-m) with bromoacetyl bromide (2) in aqueous basic medium to acquire different electrophiles, 3a-m, with good yields. These electrophiles were further reacted with 1-[(E)-3-phenyl-2-propenyl]piperazine (4) to yield the desired compounds, N-(substituted)-2-{4-[(E)-3-phenyl-2-propenyl]-1-perazinyl}acetamides (5a-m). The structures of these compounds were established from their IR, 1H-NMR, 13C-NMR, EI-MS and CHN analysis data. The bacterial biofilm inhibitory potential of these piperazine derivatives was tested against two pathogenic strains, Bacillus subtilus and Escherichia coli. Two compounds, 5d and 5h were identified as suitable antibacterial agents. The cytotoxicity of these molecules was profiled through hemolytic assay and it was inferred that all the compounds were nearly harmless for membrane of red blood cells.

Keywords

Scientia Iranica
Volume 26, Issue 6 - Serial Number 6
Transactions on Chemistry and Chemical Engineering (C)
November and December 2019
Pages 3375-3386

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