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
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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
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A New Class of Dual-Targeted Antivirals: Monophosphorylated Acyclovir Prodrug Derivatives Suppress Both Human Immunodeficiency Virus Type 1 and Herpes Simplex Virus Type 2
Christophe Vanpouille,Andrea Lisco,Marco Derudas,Elisa Saba,Jean-Charles Grivel,Beda Brichacek,Francesca Scrimieri,Raymond F. Schinazi,Dominique Schols,Christopher McGuigan,Jan Balzarini,Leonid Margolis +11 more
TL;DR: Acyclovir ProTides represent a new class of antivirals that suppress both HIV-1 and HSV-2 by directly and independently blocking the key replicative enzymes of both viruses.
Journal ArticleDOI
Enantioselective synthesis of N, O-psiconucleosides
Ugo Chiacchio,Luisa Borrello,Daniela Iannazzo,Pedro Merino,Anna Piperno,Antonio Rescifina,Barbara Richichi,Giovanni Romeo +7 more
TL;DR: The first enantioselective synthesis of β- d and β- l N, O -psiconucleosides is reported in this article, which is based on the asymmetric 1,3-dipolar cycloaddition of the C -[(4 S )-2,2-dimethyl-1, 3-dioxolan-4-yl]- N -methyl nitrone with ethyl 2-acetyloxyacrylate.
Journal ArticleDOI
Synthesis of pyrimidine 2'-deoxy ribonucleosides branched at the 2'-position via radical atom-transfer cyclization reaction with a vinylsilyl group as a radical-acceptor tether.
TL;DR: A regio- and stereoselective method for introducing a vinyl group at the position beta to a hydroxyl group in halohydrins or alpha-phenylselenoalkanols via a radical atom-transfer cyclization reaction with a vinylsilyl group as a temporary connecting radical-acceptor tether is developed.
Journal ArticleDOI
Diastereoselective Synthesis ofN,O-Psiconucleosides, a New Class of Modified Nucleosides
Ugo Chiacchio,Antonino Corsaro,Venerando Pistarà,Antonio Rescifina,Daniela Iannazzo,Anna Piperno,Giovanni Romeo,Roberto Romeo,Giovanni Grassi +8 more
TL;DR: Anomeric α- and β-N,O-psiconucleosides were prepared by 1,3-dipolar cycloaddition of C-ethoxycarbonyl N-methyl nitrone with ethyl 2-acetyloxyacrylate, followed by Vorbruggen nucleosidation as mentioned in this paper.
Journal ArticleDOI
Synthesis and biological evaluation of phosphonated dihydroisoxazole nucleosides.
Giovanni Romeo,Daniela Iannazzo,Anna Piperno,Roberto Romeo,Monica Saglimbeni,Maria A. Chiacchio,Emanuela Balestrieri,Beatrice Macchi,Antonio Mastino +8 more
TL;DR: The cytotoxicity, the anti-HSV activity and the RT-inhibitory activity of the obtained compounds were evaluated and compared with those of AZT and diethyl methylphosphonate, a saturated phosphonated dihydroisoxazole nucleoside analogue.