--------------------
- New carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane fragment as sugar moiety; synthesis, X-ray crystallography and anticancer activity. doi link

Auteur(s): Tănase Constantin I, Drăghici Constantin, Căproiu Miron Teodor, Sergiu Shova, Mathe C., Cocu Florea G, Enache Cristian, Maganu Maria

(Article) Publié: Bioorganic & Medicinal Chemistry Letters / Bioorganic And Medicinal Chemistry Letters, vol. 22 p.513-22 (2014)


Ref HAL: hal-00947583_v1
PMID 24280070
DOI: 10.1016/j.bmc.2013.10.056
Résumé:

An amine group was synthesized starting from an optically active bicyclo[2.2.1]heptane compound, which was then used to build the 5 atoms ring of a key 6-chloropurine intermediate. This was then reacted with ammonia and selected amines obtaining new adenine- and 6-substituted adenine conformationally constrained carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane skeleton in the sugar moiety. X-ray crystallography confirmed an exo-coupling of base to the ring and a L configuration of the nucleoside analogues. The compounds were tested for anticancer activity.