Design and synthesis of stable N-[2-(Aryl/heteroaryl substituted)ethyl] propanamide derivatives of (S)-ketoprofen and (S)-ibuprofen as non-ulcerogenic anti-inflammatory and analgesic agents

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dc.authorid0000-0001-6047-2796
dc.contributor.authorBerk, Barkın
dc.contributor.authorBender, Ceysu
dc.contributor.authorAkkol Küpeli, Esra
dc.contributor.authorYeşilada, Erdem
dc.date.accessioned10.07.201910:49:13
dc.date.accessioned2019-07-10T19:36:15Z
dc.date.available10.07.201910:49:14
dc.date.available2019-07-10T19:36:15Z
dc.date.issued2016
dc.departmentİstanbul Medipol Üniversitesi, Eczacılık Fakültesi, Eczacılık Meslek Bilimleri Bölümü, Farmasötik Kimya Ana Bilim Dalı
dc.description.abstractThe carboxylic acid groups of (S) ketoprofen and (S) ibuprofen were brought into reaction with substituted ethylamine derivatives to form (S)-2-(4-isobutylphenyl)- and (S)-2-(3-benzoylphenyl)-N-[2-(aryl/heteroaryl substituted) ethyl]propanamide derivatives. Then, these sets were evaluated in terms of their in vivo anti-inflammatory and analgesic properties using the carrageenan-induced paw edema and p-benzoquinone-induced writhing models. Among the synthesized compounds, (S)-2-(4-isobutylphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]propanamide (4f) showed the highest activity at the 100mg/kg dose inducing no gastric lesions when compared to the parent compound, ibuprofen. In vitro studies on chemical stability revealed that the amide derivative with the highest activity (4f) was chemically stable in simulated gastric (pH 1.2) and intestinal fluids (pH 7.4). In 80% v/v human plasma, the amide derivative was found to be stable against plasma hydrolases over the experimental period. The most active compound, (S)-2-(4-isobutylphenyl)-N-[2-(pyrrolidin-1-yl)ethyl]propanamide, was also studied in 10% rat liver homogenate (pH 7.4) to identify its release pattern as a prodrug.
dc.identifier.citationBerk, B., Bender, C., Akkol Küpeli, E. ve Yeşilada, E. (2016). Design and synthesis of stable N-[2-(Aryl/heteroaryl substituted)ethyl] propanamide derivatives of (S)-ketoprofen and (S)-ibuprofen as non-ulcerogenic anti-inflammatory and analgesic agents. Acta Pharmaceutica Sciencia, 54(1), 65-80. https://dx.doi.org/10.23893/1307-2080.APS.0546
dc.identifier.doi10.23893/1307-2080.APS.0546
dc.identifier.endpage80
dc.identifier.issn1307-2080
dc.identifier.issue1
dc.identifier.scopusqualityN/A
dc.identifier.startpage65
dc.identifier.urihttps://hdl.handle.net/20.500.12511/1111
dc.identifier.urihttps://dx.doi.org/10.23893/1307-2080.APS.0546
dc.identifier.volume54
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherUniversity of Istanbul
dc.relation.ispartofActa Pharmaceutica Scienciaen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectAnti-inflammatory
dc.subjectIbuprofen
dc.subjectKetoprofen
dc.subjectNSAIDs
dc.titleDesign and synthesis of stable N-[2-(Aryl/heteroaryl substituted)ethyl] propanamide derivatives of (S)-ketoprofen and (S)-ibuprofen as non-ulcerogenic anti-inflammatory and analgesic agents
dc.typeArticle

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