Synthesis of novel ceramide-like penetration enhancers

Ceramide-like penetration enhancers have been synthesized by isosteric replacements of the 1-hydroxymethyl and amide moieties of natural ceramides. Metabolically more stable oxime and five-membered heterocyclic (1,2,4-oxadiazole, 1,2,4-triazole, tetrazole) analogues are more polar and possess H-bond...

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Veröffentlicht in:	Tetrahedron letters 2011-04, Vol.52 (16), p.1863-1865
Hauptverfasser:	Takács, Mária, Bubenyák, Máté, Váradi, András, Blazics, Balázs, Horváth, Péter, Kökösi, József
Format:	Artikel
Sprache:	eng
Schlagworte:	Amides Ceramide Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Isostere replacement Lipids Optimization Organic chemistry Oxime Oximes Penetration Penetration enhancer Preparations and properties Synthesis (chemistry) Tetrahedrons Tetrazoles
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Beschreibung
Zusammenfassung:	Ceramide-like penetration enhancers have been synthesized by isosteric replacements of the 1-hydroxymethyl and amide moieties of natural ceramides. Metabolically more stable oxime and five-membered heterocyclic (1,2,4-oxadiazole, 1,2,4-triazole, tetrazole) analogues are more polar and possess H-bond acceptor properties, which make them potentially useful in optimizing key intermolecular features in interactions between the modified ceramide structures and the lipid layers of stratum corneum.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2011.02.024