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,* email
Received: 18 February 2008; in revised form: 8 March 2008 / Accepted: 10 March 2008 / Published: 18 March 2008
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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.

AMA Style

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.

Chicago/Turabian Style

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.

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