Skip to main content
Vai all'homepage della Commissione europea (si apre in una nuova finestra)
italiano it
CORDIS - Risultati della ricerca dell’UE
CORDIS
Contenuto archiviato il 2024-06-18

A biomimetic synthesis of Haouamine A and analogues

Obiettivo

Haouamines A and B were isolated in 2003 by Zubia and co-workers from the Ascidian Aplidium haouarianum, collected off the coast of southern Spain. Haouamine A was found to exhibit selective cytotoxicity against a human colon cancer cell line (HT-29, IC50 = 0.1 µgml-1, 200nM). From a structural standpoint, these novel polycyclic alkaloid metabolites exhibit several fascinating features: both alkaloids feature an indeno tetrahydropyrimidine moiety that contains a diaryl quaternary center and anti-Bredt double bond. The tetrahydropyridine ring is fused to a highly strained 11-membered cyclophane ring system. In addition, NMR studies have shown that they exist in solution as a dynamic 2:1 interconverting mixture of stereoisomers generated either by nitrogen inversion or by atropisomerism of the biaryl unit. Of even greater import, the uniquely strained nature of the 3-aza-[7]-paracyclophane unit has been clearly revealed by X-Ray crystallography and the non-planar south-eastern aromatic ring is in fact so deformed that it exists in a boatlike conformation. The combination of interesting biological activity and novel chemical structure makes the haouamines attractive targets for synthesis.

Campo scientifico (EuroSciVoc)

Parole chiave

Argomento(i)

Invito a presentare proposte

FP7-PEOPLE-2007-2-1-IEF
Vedi altri progetti per questo bando

Meccanismo di finanziamento

MC-IEF - Intra-European Fellowships (IEF)

Coordinatore

UNIVERSITY COLLEGE LONDON
Contributo UE
€ 169 390,93
Costo totale
Nessun dato