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Molecules 2015, 20(10), 18789-18807; doi:10.3390/molecules201018789

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

1
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, 90-151 Lodz, Muszyńskiego 1, Poland
2
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 Synthesis)
View Full-Text   |   Download PDF [834 KB, uploaded 16 October 2015]   |  

Abstract

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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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

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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