Phosphoramidate derivatives of acyclovir: Synthesis and antiviral activity in HIV-1 and HSV-1 models in vitro

Bioorganic & Medicinal Chemistry
2012.0

Abstract

The antiviral activity against HIV and HSV and the chemical stability of ACV phosphoramidate derivatives were studied. The phosphoramidates of ACV demonstrated moderate activity. The best compound appeared to be 9-(2-hydroxymethyl)guanine phosphoromonomorpholidate (7), which inhibited virus replication in pseudo-HIV-1 particles by 50% at 50 μM. It also inhibited replication of wild-type HSV-1 (9.7 μM) as well as an acyclovir-resistant strain (25 μM). None of the synthesised compounds showed any cytotoxicity.

Knowledge Graph

Similar Paper

Phosphoramidate derivatives of acyclovir: Synthesis and antiviral activity in HIV-1 and HSV-1 models in vitro
Bioorganic & Medicinal Chemistry 2012.0
The Application of Phosphoramidate Protide Technology to Acyclovir Confers Anti-HIV Inhibition
Journal of Medicinal Chemistry 2009.0
Synthesis and antiviral activity of novel N-substituted derivatives of acyclovir
Journal of Medicinal Chemistry 1988.0
Synthesis, enzymatic phosphorylation and antiviral activity of acyclic dienyl phosphonate derivatives of guanine
Bioorganic & Medicinal Chemistry Letters 1996.0
Modifications on the heterocyclic base of acyclovir: syntheses and antiviral properties
Journal of Medicinal Chemistry 1985.0
Synthesis and antiviral activity of the nucleotide analog (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cystosine
Journal of Medicinal Chemistry 1989.0
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives
Bioorganic & Medicinal Chemistry 2019.0
Synthesis and antiherpetic activity of (.+-.)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds
Journal of Medicinal Chemistry 1988.0
Synthesis and Antiviral Activity of Novel Acyclic Nucleosides:  Discovery of a Cyclopropyl Nucleoside with Potent Inhibitory Activity against Herpesviruses
Journal of Medicinal Chemistry 1998.0
Synthesis and antiherpes virus activity of phosphate and phosphonate derivatives of 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine
Journal of Medicinal Chemistry 1986.0