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

Bioorganic & Medicinal Chemistry Letters
2004.0

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.

Knowledge Graph

Similar Paper

Synthesis and anti-HCMV activity of 1-acyl-β-lactams and 1-acylazetidines derived from phenylalanine
Bioorganic & Medicinal Chemistry Letters 2004.0
From 1-Acyl-β-lactam Human Cytomegalovirus Protease Inhibitors to 1-Benzyloxycarbonylazetidines with Improved Antiviral Activity. A Straightforward Approach To Convert Covalent to Noncovalent Inhibitors
Journal of Medicinal Chemistry 2005.0
Design and Synthesis of Pyrrolidine-5,5‘-trans-Lactams (5-Oxo-hexahydropyrrolo[3,2-b]pyrroles) as Novel Mechanism-Based Inhibitors of Human Cytomegalovirus Protease. 4. Antiviral Activity and Plasma Stability
Journal of Medicinal Chemistry 2003.0
Synthesis and anti-HCMV activity of 1-[ω-(phenoxy)alkyl]uracil derivatives and analogues thereof
Bioorganic & Medicinal Chemistry 2013.0
Synthesis and SAR studies on azetidine-containing dipeptides as HCMV inhibitors
Bioorganic & Medicinal Chemistry 2011.0
Synthesis of N-Alkyl Substituted Indolocarbazoles as Potent Inhibitors of Human Cytomegalovirus Replication
Bioorganic & Medicinal Chemistry Letters 2001.0
Phosphoramidate derivatives of acyclovir: Synthesis and antiviral activity in HIV-1 and HSV-1 models in vitro
Bioorganic & Medicinal Chemistry 2012.0
Synthesis and anti-VZV activity of 6-heteroaryl derivatives of tricyclic acyclovir and 9-{[cis-1′,2′-bis(hydroxymethyl)cycloprop-1′-yl]methyl}guanine analogues
European Journal of Medicinal Chemistry 2009.0
Toward the discovery of dual HCMV–VZV inhibitors: Synthesis, structure activity relationship analysis, and cytotoxicity studies of long chained 2-uracil-3-yl-N-(4-phenoxyphenyl)acetamides
Bioorganic & Medicinal Chemistry 2015.0
N-Aryl 3-halogenated azetidin-2-ones and benzocarbacephems, inhibitors of .beta.-lactamases
Journal of Medicinal Chemistry 1988.0