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Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives

The current study focuses on the synthesis of several hybrid individuals combining a natural oleanolic acid skeleton and synthetic nonsteroidal anti-inflammatory drug moieties (NSAIDs). It studied structural modifications of the oleanolic acid structure by use of the direct reactivity of hydroxyl or...

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Autores principales: Pawełczyk, Anna, Olender, Dorota, Sowa-Kasprzak, Katarzyna, Zaprutko, Lucjusz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273679/
https://www.ncbi.nlm.nih.gov/pubmed/27077841
http://dx.doi.org/10.3390/molecules21040420
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author Pawełczyk, Anna
Olender, Dorota
Sowa-Kasprzak, Katarzyna
Zaprutko, Lucjusz
author_facet Pawełczyk, Anna
Olender, Dorota
Sowa-Kasprzak, Katarzyna
Zaprutko, Lucjusz
author_sort Pawełczyk, Anna
collection PubMed
description The current study focuses on the synthesis of several hybrid individuals combining a natural oleanolic acid skeleton and synthetic nonsteroidal anti-inflammatory drug moieties (NSAIDs). It studied structural modifications of the oleanolic acid structure by use of the direct reactivity of hydroxyl or hydroxyimino groups at position C-3 of the triterpenoid skeleton with the carboxylic function of anti-inflammatory drugs leading to new perspective compounds with high potential pharmacological activities. Novel ester- and iminoester-type derivatives of oleanolic unit with the different NSAIDs, such as ibuprofen, aspirin, naproxen, and ketoprofen, were obtained and characterized. Moreover, preliminary research of compounds obtaining structure stability under acidic conditions was examined and the PASS method of prediction of activity spectra for substances was used to estimate the potential biological activity of these compounds.
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spelling pubmed-62736792018-12-28 Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives Pawełczyk, Anna Olender, Dorota Sowa-Kasprzak, Katarzyna Zaprutko, Lucjusz Molecules Article The current study focuses on the synthesis of several hybrid individuals combining a natural oleanolic acid skeleton and synthetic nonsteroidal anti-inflammatory drug moieties (NSAIDs). It studied structural modifications of the oleanolic acid structure by use of the direct reactivity of hydroxyl or hydroxyimino groups at position C-3 of the triterpenoid skeleton with the carboxylic function of anti-inflammatory drugs leading to new perspective compounds with high potential pharmacological activities. Novel ester- and iminoester-type derivatives of oleanolic unit with the different NSAIDs, such as ibuprofen, aspirin, naproxen, and ketoprofen, were obtained and characterized. Moreover, preliminary research of compounds obtaining structure stability under acidic conditions was examined and the PASS method of prediction of activity spectra for substances was used to estimate the potential biological activity of these compounds. MDPI 2016-04-12 /pmc/articles/PMC6273679/ /pubmed/27077841 http://dx.doi.org/10.3390/molecules21040420 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Pawełczyk, Anna
Olender, Dorota
Sowa-Kasprzak, Katarzyna
Zaprutko, Lucjusz
Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives
title Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives
title_full Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives
title_fullStr Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives
title_full_unstemmed Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives
title_short Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives
title_sort hybrid compounds strategy in the synthesis of oleanolic acid skeleton-nsaid derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273679/
https://www.ncbi.nlm.nih.gov/pubmed/27077841
http://dx.doi.org/10.3390/molecules21040420
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