Next Article in Journal
Prodrugs for the Treatment of Neglected Diseases
Previous Article in Journal
Cytotoxic Metabolites from the Okinawan Ascidian Diplosoma virens
Article Menu

Export Article

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

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

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
View Full-Text   |   Download PDF [373 KB, uploaded 18 June 2014]   |  

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. View Full-Text
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
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top