Synthesis and anti-HCMV activity of 1-acyl-beta-lactams and 1-acylazetidines derived from phenylalanine

  • Bioorg Med Chem Lett. 2004 May 3;14(9):2253-6. doi: 10.1016/j.bmcl.2004.02.010.
Guillermo Gerona-Navarro  1 ,  M Jesús Pérez de Vega ,  M Teresa García-López ,  Graciela Andrei ,  Robert Snoeck ,  Jan Balzarini ,  Erik De Clercq ,  Rosario González-Muñiz
Affiliations
  • 1. Instituto de Química Médica (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.
PMID: 15081019 DOI: 10.1016/j.bmcl.2004.02.010
Abstract

Different Phe-derived 1-acyl-beta-lactams, analogous to a series of 2-azetidinones acting as HCMV serine Protease Inhibitors, were synthesized. Some of these compounds were modest inhibitors of the HCMV replication. Interestingly, removal of the carbonyl group of the beta-lactam ring, most likely acting as the serine trap, resulted in an azetidine derivative with anti-HCMV activity comparable to that of the reference compound ganciclovir.