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Docking Studies and alpha-Substitution Effects on the Anti-Inflammatory Activity of beta-Hydroxy-beta-arylpropanoic Acids

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2011
1481.pdf (531.3Kb)
Authors
Savić, Jelena
Dilber, Sanda
Marković, Bojan
Milenković, Marina
Vladimirov, Sote
Juranić, Ivan O.
Article (Published version)
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Abstract
Six beta-hydroxy-beta-aryl propanoic acids were synthesised using a modification of Reformatsky reaction which has already been reported. These acids belong to the aryl propanoic acid class of compounds, structurally similar to the NSAIDs, such as ibuprofen, and an anti-inflammatory activity is thus expected. The aim of this work was to determine anti-inflammatory activity, examine gastric tolerability, and to carry out molecular docking experiments to identify potential COX-2 inhibitors among the beta-hydroxy-beta-aryl propanoic acids, and to elucidate the effect a-methyl substitution on the anti-inflammatory activity. Anti-inflammatory activity and gastric tolerability were determined on rats using carragenan induced paw oedema method, and docking studies were carried out using Autodock v4.0.1. The range of ED(50) values is between 127 mu mol/kg and 15 mu mol/kg, while the result for ibuprofen is 51.7 mu mol/kg. Only slight hyperaemia or few petechiae were spotted on rat's stomach. T...he results indicate that all compounds possess significant anti-inflammatory activity after oral administration, and that 2-methyl-3-hydroxy-3,3-diphenylpropanoic acid has greatest activity, surpassing that of ibuprofen, a standard NSAID. Another compound, 3-hydroxy-3,3-diphenylpropanoic acid, shows activity matching that of ibuprofen, and is non-chiral and is proven to be non-toxic. The most of investigated compounds have interactions with P3 anchor site like COX-2 selective inhibitors. No tested substances or ibuprofen produced any significant gastric lesions.

Keywords:
beta-hydroxy-beta-arylpropanoic acids / Reformatsky reaction / anti-inflammatory activity / molecular docking simulations / COX-2 selective inhibitor
Source:
Molecules, 2011, 16, 8, 6645-6655
Publisher:
  • MDPI, Basel
Projects:
  • Development of molecules with antiinflammatory and cardioprotective activity: structural modifications, modelling, physicochemical characterization and formulation investigations (RS-172041)

DOI: 10.3390/molecules16086645

ISSN: 1420-3049

PubMed: 25134768

WoS: 000294249100036

Scopus: 2-s2.0-80052214202
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URI
http://farfar.pharmacy.bg.ac.rs/handle/123456789/1483
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  • Radovi istraživača / Researchers’ publications
Institution
Pharmacy

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