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Molecules 2016, 21(4), 420; doi:10.3390/molecules21040420

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

Department of Organic Chemistry, Pharmaceutical Faculty, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland
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Academic Editor: Derek J. McPhee
Received: 8 February 2016 / Revised: 15 March 2016 / Accepted: 23 March 2016 / Published: 12 April 2016
(This article belongs to the Section Organic Synthesis)
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Abstract

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. View Full-Text
Keywords: oleanolic acid; oleanolic oxime; NSAIDs; ibuprofen; aspirin; naproxen; ketoprofen; hybrid compounds oleanolic acid; oleanolic oxime; NSAIDs; ibuprofen; aspirin; naproxen; ketoprofen; hybrid compounds
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Pawełczyk, A.; Olender, D.; Sowa-Kasprzak, K.; Zaprutko, L. Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives. Molecules 2016, 21, 420.

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