Bis-14-membered ring diketal diamines: Synthesis and evaluation of their anti-HIV and anti-tumoral activities. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Medicinal Chemistry Année : 2009

Bis-14-membered ring diketal diamines: Synthesis and evaluation of their anti-HIV and anti-tumoral activities.

Résumé

Chiral and achiral macrocyclic bis-diketal diamines, analogs of bicyclam AMD 3100, were synthesized in three steps from the previously obtained 14-membered ring diketal dilactams. Their monoreduction with lithium aluminium hydride gave the corresponding diketal aminolactams. Coupling these with dibromo-p-xylene led to xylyl dimer compounds. A second reduction step yielded the expected bis-diketal diamines in the methyl and unsubstituted series. Biological tests on the unreduced and reduced dimers showed both weak anti-HIV and anti-proliferative activities for the bis-diphenyl diketal aminolactam 13b, with a mode of action probably different from that of AMD 3100.
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Dates et versions

hal-00384465 , version 1 (15-05-2009)

Identifiants

Citer

Radouane Affani, Franck Pélissier, Anne-Marie Aubertin, Denise Dugat. Bis-14-membered ring diketal diamines: Synthesis and evaluation of their anti-HIV and anti-tumoral activities.. European Journal of Medicinal Chemistry, 2009, 44, epub ahead of print. ⟨10.1016/j.ejmech.2009.03.008⟩. ⟨hal-00384465⟩
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