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 | Zendy

Shuai Tan | Zendy; Elisabetta Groaz | Zendy; Mark N. Prichard | Zendy; Raj Kalkeri | Zendy; Roger G. Ptak | Zendy; Piet Herdewijn | Zendy

Open Access

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

Author(s) -

Shuai Tan,

Elisabetta Groaz,

Mark N. Prichard,

Raj Kalkeri,

Roger G. Ptak,

Piet Herdewijn

Publication year - 2021

Publication title -

rsc medicinal chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.754

H-Index - 55

ISSN - 2632-8682

DOI - 10.1039/d1md00086a

Subject(s) - thymine , stereochemistry , chemistry , hepatitis b virus , derivative (finance) , nucleoside , nucleoside analogue , virus , virology , biology , biochemistry , dna , financial economics , economics

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; EC 50 = 0.33 μM), without significant antiretroviral activity. These findings suggest new strategies to synthesize unique ANPs with a targeted antiviral profile.

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