Synthesis and SAR studies on azetidine-containing dipeptides as HCMV inhibitors
2011
Pérez-Faginas, Paula | Aranda, M Teresa | García-López, M Teresa | Snoeck, Robert | Andrei, Graciela | Balzarini, Jan | González-Muñiz, Rosario
SAR studies on an azetidine-containing dipeptide prototype inhibitor of HCMV are described. Three series of structurally modified analogues, involving substitutions at the N- and C-terminus, and at the C-terminal side-chain were synthesized and evaluated for antiviral activity. Aliphatic or no substituents at the C-carboxamide group, an aliphatic C-terminal side-chain, as well as a benzyloxycarbonyl moiety at the N-terminus were absolute requirements for anti-HCMV activity. The conformational restriction induced by the 2-azetidine residue into the dipeptide derivatives, identified by ¹H NMR as a γ-type reverse turn, seems to have influence on the activity of these molecules.
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