Issue 5, 2021

Introduction of a cyano group at the 2-position of an (R,S)-3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) derivative of thymine elicits selective anti-HBV activity

Abstract

The substantial impact of acyclic nucleoside phosphonates (ANPs) on human medicine encourages the synthesis of new ANP analogues with a potentially differentiated antiviral spectrum. Herein, we demonstrate the functionalization of the 2-position of the (R,S)-3-hydroxy-2-(phosphonomethoxy)propyl side-chain of an inactive ANP with a polar cyano group to generate a thymine analogue with selective inhibition of hepatitis B virus (HBV) replication (SI > 302; EC50 = 0.33 μM), without significant antiretroviral activity. These findings suggest new strategies to synthesize unique ANPs with a targeted antiviral profile.

Graphical abstract: Introduction of a cyano group at the 2-position of an (R,S)-3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) derivative of thymine elicits selective anti-HBV activity

Supplementary files

Article information

Article type
Research Article
Submitted
12 mar 2021
Accepted
26 mar 2021
First published
29 abr 2021

RSC Med. Chem., 2021,12, 804-808

Introduction of a cyano group at the 2-position of an (R,S)-3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) derivative of thymine elicits selective anti-HBV activity

S. Tan, E. Groaz, M. N. Prichard, R. Kalkeri, R. Ptak and P. Herdewijn, RSC Med. Chem., 2021, 12, 804 DOI: 10.1039/D1MD00086A

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