title: Hybrid Compounds Strategy in the Synthesis of Oleanolic Acid Skeleton-NSAID Derivatives.
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.
authors.affiliation: Department of Organic Chemistry, Pharmaceutical Faculty, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland. apaw@ump.edu.pl.
authors.forename: Anna
authors.initials: A
authors.lastname: Pawełczyk
authors.affiliation: Department of Organic Chemistry, Pharmaceutical Faculty, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland. dolender@ump.edu.pl.
authors.forename: Dorota
authors.initials: D
authors.lastname: Olender
authors.affiliation: Department of Organic Chemistry, Pharmaceutical Faculty, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland. kasik@ump.edu.pl.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Sowa-Kasprzak
authors.affiliation: Department of Organic Chemistry, Pharmaceutical Faculty, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznań, Poland. zaprutko@ump.edu.pl.
authors.forename: Lucjusz
authors.initials: L
authors.lastname: Zaprutko
mesh_terms: D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry*; D001241:Aspirin / Q000737:chemistry / Q000627:therapeutic use; D006801:Humans; D007052:Ibuprofen / Q000737:chemistry / Q000627:therapeutic use; D007249:Inflammation / Q000188:drug therapy*; D007660:Ketoprofen / Q000737:chemistry / Q000627:therapeutic use; D015394:Molecular Structure; D009288:Naproxen / Q000737:chemistry / Q000627:therapeutic use; D009828:Oleanolic Acid / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000893:Anti-Inflammatory Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D009288:Naproxen; D009828:Oleanolic Acid; D007660:Ketoprofen; D001241:Aspirin; D007052:Ibuprofen
keywords: NSAIDs; aspirin; hybrid compounds; ibuprofen; ketoprofen; naproxen; oleanolic acid; oleanolic oxime