Article

Design and synthesis of novel piperazine unit condensed 2,6-diarylpiperidin-4-one derivatives as antituberculosis and antimicrobial agents

Medicinal Chemistry Research (impact factor: 1.27). 04/2012; 21(5):653-662. DOI:10.1007/s00044-011-9573-9 pp.653-662

ABSTRACT AbstractA new series of 1-[2-(4-ethoxycarbonylpiperazine-1-yl)acetyl]-2,6-diarylpiperidin-4-ones (3a–3j) has been synthesized by conventional method and were characterized by IR, elemental analysis, mass spectral, 1H NMR, 13C NMR, and single crystal X-ray diffraction analysis. The synthesized compounds were evaluated for their antituberculosis
activity against Mycobacterium tuberculosis H37Rv (ATCC-27294) and also its antimicrobial activity were examined against five familiar bacterial and fungal strains.
Among the synthesized compounds, compounds 3e–3j exhibit higher inhibition potency (16μg/ml) against M. tuberculosis H37Rv. Furthermore, compounds containing fluoro substituent in the phenyl ring at C-2 and C-6 positions of the piperidin-4-one
motif (compounds 3c, 3d, and 3i) exerted better antibacterial and antifungal activity than the other phenyl-substituted compounds.

Graphical Abstract2,6-Diarylpiperidin-4-ones upon strategical N-chloroacetylation followed by base catalyzed condensation with N-ethoxycarbonylpiperazine
afforded the novel 1-(2-(4-ethoxycarbonylpiperazine-1-yl) acetyl-2,6-diarylpiperidin-4-ones.

KeywordsPiperidin-4-ones–Piperazine–Antituberculosis study–Antimicrobial activity

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Keywords

1-[2-(4-ethoxycarbonylpiperazine-1-yl)acetyl]-2,6-diarylpiperidin-4-ones
 
1H NMR
 
AbstractA new series
 
antibacterial
 
antimicrobial activity
 
compounds 3e–3j exhibit higher inhibition potency
 
conventional method
 
elemental analysis
 
fluoro substituent
 
Graphical Abstract2,6-Diarylpiperidin-4-ones
 
KeywordsPiperidin-4-ones–Piperazine–Antituberculosis study–Antimicrobial activity
 
M. tuberculosis H37Rv
 
Mycobacterium tuberculosis H37Rv
 
N-ethoxycarbonylpiperazine
 
phenyl ring