Synthesis and antibacterial profile of novel azomethine derivatives of β-phenylacrolein moiety

  • Sridevi Chigurupati
  • Neeraj Kumar Fuloria
  • Shivkanya Fuloria
  • Sundram Karupiah
  • Ravichandran Veerasamy
  • Appala Raju Nemala
  • Lim Jun Yi
  • Ang xiang Ilan
  • Syed Adnan Ali Shah
Keywords: Acrolein, Imines, Azomethine, Antibacterial, Gentamycin, Minimum inhibitory concentration

Abstract

Purpose: To develop some novel molecules effective against antibiotic-resistant bacterial infections.
Methods: A series of azomethines (SB-1 to SB-6) were synthesized from β-phenyl acrolein moiety. The structures of the synthesized compounds were confirmed on the basis of their UV ultra-violet (UV) spectroscopy (λmax: 200 - 400 nm), Fourier transform infra-red (FTIR, vibrational frequency: 500-4000 cm-1), 1H nuclear magnetic resonance (NMR, chemical shift: 0 - 10 ppm), 13C NMR (chemical shift: 0 - 200 ppm), mass spectrometry (m/z values: 0 - 500) and carbon hydrogen nitrogen (CHN) elemental analysis. The new compounds were screened for antibacterial activity by test-tube dilution and disc diffusion methods using gentamicin as reference standard.
Results: The structures of azomethine were in full agreement with their spectral data. Among all the synthesized compounds, compounds SB-5 and SB-6 exhibited the highest minimum inhibitory concentration (MIC) of 62.5 μg/mL. At MIC of 250 μg/mL, all compounds SB-1 to SB-6 displayed significant antibacterial activity, compared to gentamycin (p < 0.05). SB-5 and SB-6 were active against S. aureus, P. aeruginosa and K. pneumoniae; SB-3 was active against B. subtilis and S. aureus. SB-4 was active against P. aeruginosa and S. aureus while SB-1 and SB-2 were active against S. aureus.
Conclusion: The synthesized compounds possess antibacterial activities compared to those of gentamycin.

Keywords: Acrolein, Imines, Azomethine, Antibacterial, Gentamycin, Minimum inhibitory concentration

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eISSN: 1596-9827
print ISSN: 1596-5996