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Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids

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2008
1099.pdf (372.7Kb)
Autori
Dilber, Sanda
Dobrić, Silva
Juranić, Zorica
Marković, Bojan
Vladimirov, Sote
Juranić, Ivan O.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentu
Apstrakt
The article describes a two-step synthesis of diastereomeric 3-hydroxy-2methyl-3-( 4-biphenylyl) butanoic acids. In the first step an intermediate alpha-bromo propanoic acid 1-ethoxyethyl ester was synthesized. The second step is a new modified Reformatsky reaction in presence of Zn in tetrahydrofuran (THF) at -5 to 10 C between the previously synthesized intermediate and 4-acetylbiphenyl. Synthesis of the other studied beta-hydroxy- beta-arylpropanoic acids has already been reported. These beta-hydroxy-beta-arylpropanoic acids belong to the arylpropanoic acid class of compounds, structurally similar to the NSAIDs such as ibuprofen. The anti-inflammatory activity and gastric tolerability of the synthesized compounds were evaluated. Molecular docking experiments were carried out to identify potential COX-2 inhibitors among the beta-hydroxy- beta-aryl-alkanoic acids class. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration and... that the compounds 2-(9-( 9-hydroxy-fluorenyl))-2-methylpropanoic acid ( 5) and 3-hydroxy-3,3-diphenyl- propanoic acid (3) possess the strongest anti-inflammatory activity, comparable to that of ibuprofen, a standard NSAID, and that none of tested substances or ibuprofen produced any significant gastric lesions.

Ključne reči:
beta-Hydroxy-beta-arylalkanoic acids / Reformatsky reaction / anti-inflammatory / activity / molecular docking simulations / COX-2 selective inhibitor
Izvor:
Molecules, 2008, 13, 3, 603-615
Izdavač:
  • Molecular Diversity Preservation Int, Basel
Finansiranje / projekti:
  • Sinteza, karakterizacija i aktivnost organskih i koordinacionih jedinjenja i njihova primena u (bio)nanotehnologiji (RS-142010)
  • Supstance za farmaceutsku upotrebu: modeliranje, sinteza, fizičko-hemijske i biološke osobine, stepen čistoće i ispitivanje doziranih oblika (RS-142072)

DOI: 10.3390/molecules13030603

ISSN: 1420-3049

PubMed: 18463569

WoS: 000254464700010

Scopus: 2-s2.0-41649119732
[ Google Scholar ]
25
20
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/1101
Kolekcije
  • Radovi istraživača / Researchers’ publications
Institucija/grupa
Pharmacy
TY  - JOUR
AU  - Dilber, Sanda
AU  - Dobrić, Silva
AU  - Juranić, Zorica
AU  - Marković, Bojan
AU  - Vladimirov, Sote
AU  - Juranić, Ivan O.
PY  - 2008
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1101
AB  - The article describes a two-step synthesis of diastereomeric 3-hydroxy-2methyl-3-( 4-biphenylyl) butanoic acids. In the first step an intermediate alpha-bromo propanoic acid 1-ethoxyethyl ester was synthesized. The second step is a new modified Reformatsky reaction in presence of Zn in tetrahydrofuran (THF) at -5 to 10 C between the previously synthesized intermediate and 4-acetylbiphenyl. Synthesis of the other studied beta-hydroxy- beta-arylpropanoic acids has already been reported. These beta-hydroxy-beta-arylpropanoic acids belong to the arylpropanoic acid class of compounds, structurally similar to the NSAIDs such as ibuprofen. The anti-inflammatory activity and gastric tolerability of the synthesized compounds were evaluated. Molecular docking experiments were carried out to identify potential COX-2 inhibitors among the beta-hydroxy- beta-aryl-alkanoic acids class. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration and that the compounds 2-(9-( 9-hydroxy-fluorenyl))-2-methylpropanoic acid ( 5) and 3-hydroxy-3,3-diphenyl- propanoic acid (3) possess the strongest anti-inflammatory activity, comparable to that of ibuprofen, a standard NSAID, and that none of tested substances or ibuprofen produced any significant gastric lesions.
PB  - Molecular Diversity Preservation Int, Basel
T2  - Molecules
T1  - Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids
VL  - 13
IS  - 3
SP  - 603
EP  - 615
DO  - 10.3390/molecules13030603
ER  - 
@article{
author = "Dilber, Sanda and Dobrić, Silva and Juranić, Zorica and Marković, Bojan and Vladimirov, Sote and Juranić, Ivan O.",
year = "2008",
abstract = "The article describes a two-step synthesis of diastereomeric 3-hydroxy-2methyl-3-( 4-biphenylyl) butanoic acids. In the first step an intermediate alpha-bromo propanoic acid 1-ethoxyethyl ester was synthesized. The second step is a new modified Reformatsky reaction in presence of Zn in tetrahydrofuran (THF) at -5 to 10 C between the previously synthesized intermediate and 4-acetylbiphenyl. Synthesis of the other studied beta-hydroxy- beta-arylpropanoic acids has already been reported. These beta-hydroxy-beta-arylpropanoic acids belong to the arylpropanoic acid class of compounds, structurally similar to the NSAIDs such as ibuprofen. The anti-inflammatory activity and gastric tolerability of the synthesized compounds were evaluated. Molecular docking experiments were carried out to identify potential COX-2 inhibitors among the beta-hydroxy- beta-aryl-alkanoic acids class. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration and that the compounds 2-(9-( 9-hydroxy-fluorenyl))-2-methylpropanoic acid ( 5) and 3-hydroxy-3,3-diphenyl- propanoic acid (3) possess the strongest anti-inflammatory activity, comparable to that of ibuprofen, a standard NSAID, and that none of tested substances or ibuprofen produced any significant gastric lesions.",
publisher = "Molecular Diversity Preservation Int, Basel",
journal = "Molecules",
title = "Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids",
volume = "13",
number = "3",
pages = "603-615",
doi = "10.3390/molecules13030603"
}
Dilber, S., Dobrić, S., Juranić, Z., Marković, B., Vladimirov, S.,& Juranić, I. O.. (2008). Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids. in Molecules
Molecular Diversity Preservation Int, Basel., 13(3), 603-615.
https://doi.org/10.3390/molecules13030603
Dilber S, Dobrić S, Juranić Z, Marković B, Vladimirov S, Juranić IO. Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids. in Molecules. 2008;13(3):603-615.
doi:10.3390/molecules13030603 .
Dilber, Sanda, Dobrić, Silva, Juranić, Zorica, Marković, Bojan, Vladimirov, Sote, Juranić, Ivan O., "Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids" in Molecules, 13, no. 3 (2008):603-615,
https://doi.org/10.3390/molecules13030603 . .

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