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Molecules 2015, 20(4), 5260-5275; doi:10.3390/molecules20045260

Synthesis and Biological Properties of 5-(1H-1,2,3-Triazol-4-yl)isoxazolidines: A New Class of C-Nucleosides

1
Dipartimento Scienze del Farmaco e Prodotti per la Salute, Università di Messina, Via S.S. Annunziata, Messina 98168, Italy
2
Dipartimento di Chimica e Tecnologie Chimiche, Università della Calabria, Via P. Bucci, 12/C, Arcavacata di Rende (CS) 87036, Italy
3
Dipartimento di Scienze Bio-mediche, Università di Catania, Via Androne 81, Catania 95124, Italy
4
Dipartimento Scienze del Farmaco, Università di Catania, Viale A. Doria 6, Catania 95125, Italy
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editors: Mahesh K. Lakshman and Fumi Nagatsugi
Received: 4 February 2015 / Revised: 9 March 2015 / Accepted: 13 March 2015 / Published: 24 March 2015
(This article belongs to the Special Issue Nucleoside Modifications)
View Full-Text   |   Download PDF [702 KB, uploaded 24 March 2015]   |  

Abstract

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. An antiproliferative effect was observed for compounds 17a and 17b: the growth inhibitory effect reaches the 50% in HepG2 and HT-29 cells and increases up to 56% in the SH-SY5Y cell line after 72 h of incubation at a 100 µM concentration. View Full-Text
Keywords: vinyl triazoles; C-Nucleosides; 1,3-dipolar cycloaddition; antiproliferative activity; microwave vinyl triazoles; C-Nucleosides; 1,3-dipolar cycloaddition; antiproliferative activity; microwave
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Giofrè, S.V.; Romeo, R.; Carnovale, C.; Mancuso, R.; Cirmi, S.; Navarra, M.; Garozzo, A.; Chiacchio, M.A. Synthesis and Biological Properties of 5-(1H-1,2,3-Triazol-4-yl)isoxazolidines: A New Class of C-Nucleosides. Molecules 2015, 20, 5260-5275.

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