Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids
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 (...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2008-03-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/13/3/603/ |
| _version_ | 1811343854717108224 |
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| author | Ivan O. Juranic Sote M. Vladimirov Bojan D. Markovic Zorica D. Juranic Silva Lj. Dobric Sanda P. Dilber |
| author_facet | Ivan O. Juranic Sote M. Vladimirov Bojan D. Markovic Zorica D. Juranic Silva Lj. Dobric Sanda P. Dilber |
| author_sort | Ivan O. Juranic |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-13T19:36:11Z |
| format | Article |
| id | doaj.art-097fd6d9888a410bb3ad5f0857971451 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T19:36:11Z |
| publishDate | 2008-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-097fd6d9888a410bb3ad5f08579714512022-12-22T02:33:00ZengMDPI AGMolecules1420-30492008-03-0113360361510.3390/molecules13030603Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic AcidsIvan O. JuranicSote M. VladimirovBojan D. MarkovicZorica D. JuranicSilva Lj. DobricSanda P. DilberThe 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.http://www.mdpi.com/1420-3049/13/3/603/β-Hydroxy-β-arylalkanoic acidsReformatsky reactionanti-inflammatory activitymolecular docking simulationsCOX-2 selective inhibitor |
| spellingShingle | Ivan O. Juranic Sote M. Vladimirov Bojan D. Markovic Zorica D. Juranic Silva Lj. Dobric Sanda P. Dilber Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids Molecules β-Hydroxy-β-arylalkanoic acids Reformatsky reaction anti-inflammatory activity molecular docking simulations COX-2 selective inhibitor |
| title | Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids |
| title_full | Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids |
| title_fullStr | Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids |
| title_full_unstemmed | Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids |
| title_short | Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids |
| title_sort | docking studies and anti inflammatory activity of aza² hydroxy aza² arylpropanoic acids |
| topic | β-Hydroxy-β-arylalkanoic acids Reformatsky reaction anti-inflammatory activity molecular docking simulations COX-2 selective inhibitor |
| url | http://www.mdpi.com/1420-3049/13/3/603/ |
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