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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.

Invito a presentare proposte

FP7-PEOPLE-2007-2-1-IEF
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Coordinatore

UNIVERSITY COLLEGE LONDON
Contributo UE
€ 169 390,93
Indirizzo
GOWER STREET
WC1E 6BT LONDON

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Tipo di attività
Higher or Secondary Education Establishments
Contatto amministrativo
Greta Borg-Carbott (Ms.)
Collegamenti
Costo totale
Nessun dato