Tropical Journal of Pharmaceutical Research

Original Research Article | OPEN ACCESS

Synthesis, characterization and evaluation of anti-inflammatory properties of novel α, β-unsaturated ketones

Leaqaa A Alrubaie , Raheem J Muhasin, Mazin N Mousa

College of Pharmacy, University of Basrah, Basrah, Iraq;

For correspondence:- Leaqaa Alrubaie Email: Leaqaa2016@gmail.com Tel:+9647801207858

Accepted: 19 December 2019 Published: 31 January 2020

Citation: Alrubaie LA, Muhasin RJ, Mousa MN. Synthesis, characterization and evaluation of anti-inflammatory properties of novel α, β-unsaturated ketones. Trop J Pharm Res 2020; 19(1):147-154 doi: 10.4314/tjpr.v19i1.22

© 2020 The authors.
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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 ¹³C-NMR 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