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Published:
Apr 9, 2020Keywords:
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Main Article Content
Synthesis, characterization and evaluation of antiinflammatory properties of novel α, β-unsaturated ketones
Abstract
Purpose: To prepare and characterize alicyclic aromatic chalcone derivatives, and study their antibiotic and anti-inflammatory properties.
Methods: Claisen-Schmidt (aldol condensation) base-catalyzed condensation was used for preparation of chalcone derivatives (compounds I - IV), and the products were characterized using ultraviolet-visible spectroscopy (UV), FT-IR spectroscopy, proton nuclear magnetic resonance (1H-NMR), carbone 13CNMR and mass spectroscopy (MS). The antibacterial effect of the compounds was determined against Baci. cereus, Staph. Aureus, E. coli, and Pseudomonas Aeruginosa. In addition, their anti-inflammatory effects were assayed using cotton granule-induced granuloma in mice. The results were compared with those for diclofenac, a standard drug. The synthesized derivatives were subjected to theoretical studies on their stabilities, and some chemical parameters were calculated using density function theory [DFT].
Results: Using Claisen-Schmidt reaction, it was possible to prepare stable chalcone derivatives, such as derivatives of 2-(3-phenyl acryloyl)cyclopentan-1-one, with good results. Depending on the substituted group, it was also shown that the derivatives had effective biological effects. Compound IV displayed a noticeable antibacterial effect against Staph. aureus and E. coli. The prepared chalcone derivatives exerted markedly variable anti-inflammatory effects.
Conclusion: These results indicate that Claisen-Schmidt reaction is not limited to the preparation of chalcone derivatives from diphenyl structures only. Stable alicyclic aromatic structures can also be used. This results in derivatives with good biological effects.
Keywords: Chalcones, Claisen-Schmidt, Anti-inflammatory effects, Granuloma, Aldol Condensation
