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Molecules 2015, 20(10), 18789-18807;

Phosphonylated Acyclic Guanosine Analogues with the 1,2,3-Triazole Linker

Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, 90-151 Lodz, Muszyńskiego 1, Poland
Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium
Author to whom correspondence should be addressed.
Academic Editor: Maria Emília de Sousa
Received: 1 September 2015 / Revised: 15 September 2015 / Accepted: 17 September 2015 / Published: 16 October 2015
(This article belongs to the Section Organic Chemistry)
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A novel series of {4-[(2-amino-6-chloro-9H-purin-9-yl)methyl]-1H-1,2,3-triazol-1-yl}alkylphosphonates and {4-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]-1H-1,2,3-triazol-1-yl}alkylphosphonates as acyclic analogues of guanosine were synthesized and assessed for antiviral activity against a broad range of DNA and RNA viruses and for their cytostatic activity toward three cancerous cell lines (HeLa, L1210 and CEM). They were devoid of antiviral activity; however, several phosphonates were found slightly cytostatic against HeLa cells at an IC50 in the 80–210 µM range. Compounds (1R,2S)-17k and (1S,2S)-17k showed the highest inhibitory effects (IC50 = 15–30 µM) against the proliferation of murine leukemia (L1210) and human T-lymphocyte (CEM) cell lines. View Full-Text
Keywords: azidophosphonates; acyclonucleotides; 1,2,3-triazoles; cycloaddition; antiviral; cytostatic azidophosphonates; acyclonucleotides; 1,2,3-triazoles; cycloaddition; antiviral; cytostatic

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Głowacka, I.E.; Andrei, G.; Schols, D.; Snoeck, R.; Piotrowska, D.G. Phosphonylated Acyclic Guanosine Analogues with the 1,2,3-Triazole Linker. Molecules 2015, 20, 18789-18807.

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