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Molecules 2008, 13(3), 603-615; doi:10.3390/molecules13030603
Article

Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids

1, 2, 3, 1, 1 and 4,*
1 Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000 Belgrade, Serbia 2 Institute for Scientific Information, Crnotravska 17, 11000 Belgrade, Serbia 3 Institute for Oncology and Radiology of Serbia, Pasterova 14, 11000 Belgrade, Serbia 4 Faculty of Chemistry, University of Belgrade, P.O. Box 158, 11001 Belgrade, Serbia
* Author to whom correspondence should be addressed.
Received: 18 February 2008 / Revised: 8 March 2008 / Accepted: 10 March 2008 / Published: 18 March 2008
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Abstract

The article describes a two-step synthesis of diastereomeric 3-hydroxy-2-methyl-3-(4-biphenylyl)butanoic acids. In the first step an intermediate α-bromo propanoicacid 1-ethoxyethyl ester was synthesized. The second step is a new modified Reformatskyreaction in presence of Zn in tetrahydrofuran (THF) at –5 to 10 °C between the previouslysynthesized intermediate and 4-acetylbiphenyl. Synthesis of the other studied β-hydroxy-β-arylpropanoic acids has already been reported. These β-hydroxy-β-arylpropanoic acidsbelong to the arylpropanoic acid class of compounds, structurally similar to the NSAIDssuch as ibuprofen. The anti-inflammatory activity and gastric tolerability of thesynthesized compounds were evaluated. Molecular docking experiments were carried outto identify potential COX-2 inhibitors among the β-hydroxy-β-aryl-alkanoic acids class.The results indicate that all compounds possess significant anti-inflammatory activity afteroral administration and that the compounds 2-(9-(9-hydroxy-fluorenyl))-2-methylpropanoic acid (5) and 3-hydroxy-3,3-diphenyl-propanoic acid (3) possess thestrongest anti-inflammatory activity, comparable to that of ibuprofen, a standard NSAID,and that none of tested substances or ibuprofen produced any significant gastric lesions.
Keywords: β-Hydroxy-β-arylalkanoic acids; Reformatsky reaction; anti-inflammatory activity; molecular docking simulations; COX-2 selective inhibitor β-Hydroxy-β-arylalkanoic acids; Reformatsky reaction; anti-inflammatory activity; molecular docking simulations; COX-2 selective inhibitor
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Dilber, S.P.; Dobric, S.L.; Juranic, Z.D.; Markovic, B.D.; Vladimirov, S.M.; Juranic, I.O. Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids. Molecules 2008, 13, 603-615.

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