2014Current Organic ChemistryRequires access

Bioactive Carbocyclic Nucleoside Analogues - Syntheses and Properties of Entecavir

Michaela Campian, Martin Putala, Radovan Šebesta

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Abstract

Carbocyclic nucleoside analogs are highly biologically relevant compounds. A large variety of them already serve as drugs or are investigated with this aim in mind. This review analyses syntheses of major types of carbocyclic nucleoside derivatives including those of pharmacological interest. The emphasis of this review is on entecavir, a derivative exhibiting selective activity at nanomolar level against hepatitis B virus. The first subject of this review is the summary of nucleoside analogs, mainly classification and synthetic strategies employed for the preparation of these derivatives. The second part focuses on the recent developments in the field of enanti oselective approaches of synthesis of entecavir and related compounds. This paper covers the literature from 1992 to 2013. Keywords: Biological activity, carbocyclic saccharide, entecavir, non-natural nucleoside.

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Carbocyclic nucleoside analogs are highly biologically relevant compounds. A large variety of them already serve as drugs or are investigated with this aim in mind. This review analyses syntheses of major types of carbocyclic nucleoside derivatives including those of pharmacological interest. The emphasis of this review is on entecavir, a derivative exhibiting selective activity at nanomolar level against hepatitis B virus. The first subject of this review is the summary of nucleoside analogs, mainly classification and synthetic strategies employed for the preparation of these derivatives. The second part focuses on the recent developments in the field of enanti oselective approaches of synthesis of entecavir and related compounds. This paper covers the literature from 1992 to 2013. Keywords: Biological activity, carbocyclic saccharide, entecavir, non-natural nucleoside.

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Available abstract

Carbocyclic nucleoside analogs are highly biologically relevant compounds. A large variety of them already serve as drugs or are investigated with this aim in mind. This review analyses syntheses of major types of carbocyclic nucleoside derivatives including those of pharmacological interest. The emphasis of this review is on entecavir, a derivative exhibiting selective activity at nanomolar level against hepatitis B virus. The first subject of this review is the summary of nucleoside analogs, mainly classification and synthetic strategies employed for the preparation of these derivatives. The second part focuses on the recent developments in the field of enanti oselective approaches of synthesis of entecavir and related compounds. This paper covers the literature from 1992 to 2013. Keywords: Biological activity, carbocyclic saccharide, entecavir, non-natural nucleoside.

Key concepts: Entecavir, Nucleoside, Chemistry, Hepatitis a virus, Nucleoside analogue, Derivative (finance), Combinatorial chemistry, Stereochemistry

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