Truncated phosphonated C-1′-branched N,O-nucleosides: A new class of antiviral agents
Roberto Romeo,Caterina Carnovale,Salvatore V. Giofrè,Giovanni Romeo,Beatrice Macchi,Caterina Frezza,Francesca Marino-Merlo,Venerando Pistarà,Ugo Chiacchio +8 more
TLDR
Preliminary biological assays show that β-anomers are able to inhibit HIV in vitro infection at concentrations in the micromolar range and higher SI values with respect to AZT indicated that the compounds were endowed with low cytotoxicity.About:
This article is published in Bioorganic & Medicinal Chemistry.The article was published on 2012-06-01 and is currently open access. It has received 25 citations till now.read more
Citations
More filters
Journal ArticleDOI
Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry
TL;DR: This review aims to be a comprehensive and general summary of the different isoxazolidine syntheses, their use as starting building blocks for the preparation of natural compounds, and their main biological activities.
Journal ArticleDOI
Nucleoside Analogues: Synthesis and Biological Properties of Azanucleoside Derivatives
Dácil Hernández,Alicia Boto +1 more
TL;DR: The azanucleosides are nucleoside analogues where the furanose ring is replaced by a nitrogen-containing ring or chain this article, and their synthesis and their interesting biological properties are discussed in this microreview.
Journal ArticleDOI
Synthesis and biological evaluation of 3-hydroxymethyl-5-(1H-1,2,3-triazol) isoxazolidines.
Roberto Romeo,Salvatore V. Giofrè,Caterina Carnovale,Agata Campisi,Rosalba Parenti,Lorenzo Bandini,Maria A. Chiacchio +6 more
TL;DR: Biological tests show that the synthesized compounds are able to inhibit proliferation of follicular and anaplastic human thyroid cancer cell lines, with IC50 values ranging from 3.87 to 8.76 lM.
Journal ArticleDOI
Pyrimidine 2,4-Diones in the Design of New HIV RT Inhibitors
Roberto Romeo,Daniela Iannazzo,Lucia Veltri,Bartolo Gabriele,Beatrice Macchi,Caterina Frezza,Francesca Marino-Merlo,Salvatore V. Giofrè +7 more
TL;DR: A series of pyrimidine-2,4-diones linked to an isoxazolidine nucleus have been synthesized and tested as nucleoside analogs, endowed with potential anti-HIV (human immunodeficiency virus) activity.
Journal ArticleDOI
Synthesis and biological properties of 5-(1H-1,2,3-triazol-4-yl)isoxazolidines: a new class of C-nucleosides.
Salvatore V. Giofrè,Roberto Romeo,Caterina Carnovale,Raffaella Mancuso,Santa Cirmi,Michele Navarra,Adriana Garozzo,Maria A. Chiacchio +7 more
TL;DR: A novel series of C-nucleosides, featuring the presence of a 1,2,3-triazole ring linked to an isoxazolidine system, has been designed as mimetics of the pyrimidine nucleobases, and an antiproliferative effect was observed.
References
More filters
Journal ArticleDOI
Stereoselective Synthesis and Biological Evaluations of Novel 3 '-Deoxy-4 '-azaribonucleosides as Inhibitors of Hepatitis C Virus RNA Replication
Ugo Chiacchio,Luisa Borrello,Lia Crispino,Antonio Rescifina,Pedro Merino,Beatrice Macchi,Emanuela Balestrieri,Antonio Mastino,A. Piperno,Giovanni Romeo +9 more
TL;DR: It is demonstrated that synthesized pyrrolidine nucleosides represent a new template for antiviral or other biological studies and could be considered for novel combination therapy against HCV infection using nucleoside inhibitors and non-nucleoside inhibitor of HCV NS5B.
Journal ArticleDOI
Diastereoselective synthesis of N,O-psiconucleosides via 1,3-dipolar cycloadditions
Ugo Chiacchio,Antonino Corsaro,Daniela Iannazzo,Anna Piperno,Antonio Rescifina,Roberto Romeo,Giovanni Romeo +6 more
TL;DR: In this article, a flexible synthetic procedure to access a new and biologically interesting class of N, O -psiconucleosides by 1,3-dipolar cycloaddition of C -ethoxycarbonyl- N -methyl nitrone with ethyl 2-(acetyloxy)acrylate, followed by Vorbruggen nucleosidation and sodium borohydride reduction, is described.
Journal ArticleDOI
Modified nucleosides. A general and diastereoselective approach to N, O-psiconucleosides
TL;DR: In this paper, an efficient reaction route towards the new class of N,O-psiconucleosides has been designed, based on the 1,3-dipolar cycloaddition of C-[(tert-butyldiphenylsilyl)oxy]methyl-N-methyl nitrone with ethyl 2-acetyloxyacrylate, followed by nucleosidation.
Journal ArticleDOI
Diastereo- and enantioselective synthesis of N,O-nucleosides
Ugo Chiacchio,Antonino Corsaro,Daniela Iannazzo,Anna Piperno,Venerando Pistarà,Antonio Rescifina,Roberto Romeo,Giovanni Sindona,Giovanni Romeo +8 more
TL;DR: In this paper, the diastereo and enantioselective synthesis of α- and β-3′-hydroxymethyl-N,O-nucleosides is described, based on the 1,3-dipolar cycloaddition of a N-glycosyl nitrone.
Journal ArticleDOI
N-Substituted C-diethoxyphosphorylated nitrones as useful synthons for the synthesis of α-aminophosphonates
TL;DR: In this paper, a method for the synthesis of N-substituted C-phosphorylated nitrones 2 from hydroxymethylphosphonates via successive Swern oxidation and treatment with respective hydroxylamines is reported for the first time.