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.
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 . .
