Synthesis and Antiviral Evaluation of Novel Exomethylene Acyclic Nucleosides and Phosphonic Acid Nucleosides

Overview

Journal Arch Pharm (Weinheim)

Specialty Pharmacy

Date 2005 Nov 11

PMID 16281311

Citations 2

Authors

Aihong Kim

Joon Hee Hong

Affiliations

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Abstract

This paper describes a very simple synthesis route of novel acyclic nucleosides and phosphonic acid nucleosides. The condensation of the mesylates 6 and 17 with the natural nucleosidic bases (A, C, U, T) under nucleophilic substitution (K(2)CO(3), 18-Crown-6, DMF) and deprotection afforded the target nucleosides (11, 12, 13, 14) and phosphonic acid nucleosides (22, 23, 24, 25). In addition, these compounds were evaluated for their antiviral properties against various viruses. Uracil derivative 24 shows significant anti-HCMV activity (EC(50) = 10.24 microM).

Citing Articles

Design, Synthesis, and Evaluation of Anti-HBV Activity of Hybrid Molecules of Entecavir and Adefovir: Exomethylene Acycloguanine Nucleosides and Their Monophosphate Derivatives.

Imoto S, Kohgo S, Tokuda R, Kumamoto H, Aoki M, Amano M Nucleosides Nucleotides Nucleic Acids. 2015; 34(8):590-602.

PMID: 26167667 PMC: 7712530. DOI: 10.1080/15257770.2015.1037456.

Synthesis and antiviral activity evaluation of acyclic 2'-azanucleosides bearing a phosphonomethoxy function in the side chain.

Koszytkowska-Stawinska M, De Clercq E, Balzarini J Bioorg Med Chem. 2009; 17(11):3756-62.

PMID: 19442526 PMC: 7126109. DOI: 10.1016/j.bmc.2009.04.054.