Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids
2008
Аутори
Dilber, SandaDobrić, Silva
Juranić, Zorica
Marković, Bojan
Vladimirov, Sote
Juranić, Ivan O.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
beta-Hydroxy-beta-arylalkanoic acids / Reformatsky reaction / anti-inflammatory / activity / molecular docking simulations / COX-2 selective inhibitorИзвор:
Molecules, 2008, 13, 3, 603-615Издавач:
- Molecular Diversity Preservation Int, Basel
Финансирање / пројекти:
- Синтеза, карактеризација и активност органских и координационих једињења и њихова примена у (био)нанотехнологији (RS-MESTD-MPN2006-2010-142010)
- Супстанце за фармацеутску употребу: моделирање, синтеза, физичко-хемијске и биолошке особине, степен чистоће и испитивање дозираних облика (RS-MESTD-MPN2006-2010-142072)
DOI: 10.3390/molecules13030603
ISSN: 1420-3049
PubMed: 18463569
WoS: 000254464700010
Scopus: 2-s2.0-41649119732
Институција/група
PharmacyTY - 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 . .