Nuovi coniugati fra acido azelaico ed azaeterocicli: sintesi e valutazione dell'attività biologica

Orlando, Isabel (2015) Nuovi coniugati fra acido azelaico ed azaeterocicli: sintesi e valutazione dell'attività biologica. [Laurea magistrale], Università di Bologna, Corso di Studio in Chimica industriale [LM-DM270]
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The well-known antiproliferative properties of the 9-hydroxystearic acid (9-HSA) on human colon cancer cells (HT-29 cell line) have inspired this thesis work in order to obtain new derivatives maintaining the C1-C8 chain of the HSA linked to an heterocyclic moiety at the C-9 carbon atom and to investigate their biological activity. First, thiazoles, thiadiazoles and benzothiazoles, that are compounds of interest in many fields for their biological activities, have been introduced through an amide bond starting from their 2-amino precursors. The products have been obtained by treatment with methyl 9-chloro-9-oxononanoate according to a Schotten-Baumann type reaction. The acylation reaction occurred at the endocyclic nitrogen atom of the heterocycle, as ascertained through NOESY-1D experiment. After, methyl 9-chloro-9-oxononanoate was reacted with indole, N-methylindole, and triptamine giving a serie of new indole derivatives. Finally, the biological activity of some compounds has been tested through assays on HT-29 cancer cells and bacterial and fungal microorganisms; docking calculations have also been performed to evaluate the possible interactions with the active site of histone deacetylase, which are molecular targets of the 9-HSA.

Tipologia del documento
Tesi di laurea (Laurea magistrale)
Autore della tesi
Orlando, Isabel
Relatore della tesi
Correlatore della tesi
Corso di studio
Parole chiave
aza-eterocicli antitumorali antifungini acido-9-idrossistearico iston-deacetilasi
Data di discussione della Tesi
16 Ottobre 2015

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