Novel imidazo[1,2-c]pyrimidine base-modified nucleosides: synthesis and antiviral evaluation

Bioorganic & Medicinal Chemistry
Nurolaini KifliClaire Simons

Abstract

The preparation of a series of novel 6-(beta-D-ribofuranosyl)-2-alkyl/aryl-6H-imidazo[1,2-c]pyrimidin-5-one nucleosides and the 2-nitrile nucleosides, 6-(beta-D-ribofuranosyl)-5-oxo-5,6-dihydro-imidazo[1,2-c]pyrimidine-2-carbonitrile and 2R and 2S isomers of 6-(beta-D-ribofuranosyl)-5-oxo-2,3,5,6-tetrahydro-imidazo[1,2-c]pyrimidine-2-carbonitrile, is described using two synthetic approaches. The nucleoside mimetics described were evaluated against a wide range of viral types and strains in cell culture. With the exception of one nucleoside, which displayed anti-CMV activity at toxic concentrations, none of the compounds showed antiviral activity most likely due to a lack of substrate recognition by viral and/or cellular nucleoside kinases.

Citations

Apr 25, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mohamed M El SadekGalila A Yacout
May 21, 2016·Frontiers in Chemistry·Zofia Jahnz-WechmannJerzy Boryski
Mar 26, 2014·Nucleosides, Nucleotides & Nucleic Acids·Dhaval D HaveliwalaSaurabh K Patel
Jan 24, 2014·Beilstein Journal of Organic Chemistry·Anna ChentsovaAthanassios Giannis
May 5, 2018·Natural Product Research·Ayad M R RaaufHala Ayad M Rasheed
Jan 11, 2011·The Journal of Organic Chemistry·Xuesen FanJianji Wang

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