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Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids
Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000 Belgrade, Serbia
Institute for Scientific Information, Crnotravska 17, 11000 Belgrade, Serbia
Institute for Oncology and Radiology of Serbia, Pasterova 14, 11000 Belgrade, Serbia
Faculty of Chemistry, University of Belgrade, P.O. Box 158, 11001 Belgrade, Serbia
* Author to whom correspondence should be addressed.
Received: 18 February 2008; in revised form: 8 March 2008 / Accepted: 10 March 2008 / Published: 18 March 2008
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
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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.
Dilber SP, Dobric SL, Juranic ZD, Markovic BD, Vladimirov SM, Juranic IO. Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids. Molecules. 2008; 13(3):603-615.
Dilber, Sanda P.; Dobric, Silva L.; Juranic, Zorica D.; Markovic, Bojan D.; Vladimirov, Sote M.; Juranic, Ivan O. 2008. "Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids." Molecules 13, no. 3: 603-615.