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. 2014 Dec 1;22(23):6665-6671.
doi: 10.1016/j.bmc.2014.10.003. Epub 2014 Oct 13.

Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs

Jong Hyun Cho  1 , Lavanya Bondana  1 , Mervi A Detorio  1 , Cathy Montero  1 , Leda C Bassit  1 , Franck Amblard  1 , Steven J Coats  2 , Raymond F Schinazi  1
Affiliations

Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs

Jong Hyun Cho et al. Bioorg Med Chem. .

Abstract

The synthesis of 9-(β-d-1,3-dioxolan-4-yl)2,6-diaminopurine nucleoside phosphoramidate prodrugs as well as various 2-amino-6-carbamoylpurine dioxolane derivatives and their phosphoramidates prodrugs is reported. Their ability to block HIV and HBV replication along with their cytotoxicity toward HepG2, human lymphocyte, CEM and Vero cells was also assessed.

Keywords: Anti-HBV; Anti-HIV; Antiviral agent; DAPD; β-d-1,3-Dioxolan-4-yl nucleosides.

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Figures

Figure 1
Figure 1
Scheme 1
Scheme 1
Reagents and reaction conditions: a) (EtOAlaNH)P(=O)(OPh)Cl 6, t-BuMgCl, THF, −78 °C then rt, 8 h.
Scheme 2
Scheme 2
Reagents and reaction conditions: a) TBSCl, imidazole, pyridine, 0 °C then rt, 12 h; b) RCl, NMI, CH2Cl2, 0 °C then rt, 12 h; c) Et3N-3HF, THF, rt, 12 h; d) (NHAlaOEt)P(=O)(OPh)Cl 6, NMI, −78 °C then rt, 8–12 h.
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