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

• Main Authors: Chigurupati, S. (Author), Fuloria, N.K (Author), Fuloria, S. (Author), Ilan, A.X (Author), Karupiah, S. (Author), Nemala, A.R (Author), Shah, S.A.A (Author), Veerasamy, R. (Author), Yi, L.J (Author)
• Format: Article
• Language: English
• Published: University of Benin 2016
• Subjects: 4 (3 phenylallylideneamino)benzaldehyde; 4 (3 phenylallylideneamino)benzoic acid; 4 (3 phenylallylideneamino)phenol; 4 methoxy 2(3 phenylallylideneamino)benzoic acid; 4 methoxy n (3 phenylallylidene)benzamine; Acrolein; Antibacterial; antibacterial activity; Article; Azomethine; azomethine derivative; broth dilution; carbon nuclear magnetic resonance; chemical compound; chemical structure; controlled study; disk diffusion; finite element analysis; gentamicin; Gentamycin; Imines; infrared spectroscopy; mass spectrometry; minimum inhibitory concentration; Minimum inhibitory concentration; n (3 phenylallylidene)benzamine; nonhuman; proton nuclear magnetic resonance; synthesis; test tube dilution; thin layer chromatography; ultraviolet spectroscopy; unclassified drug
• Online Access: View Fulltext in Publisher; View in Scopus

 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. © Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, 300001 Nigeria. All rights reserved.