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Molecules 2016, 21(11), 1420; doi:10.3390/molecules21111420

Synthesis and the Biological Activity of Phosphonylated 1,2,3-Triazolenaphthalimide Conjugates

1
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszyńskiego 1, 90-151 Lodz, Poland
2
Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium
*
Author to whom correspondence should be addressed.
Academic Editor: D. Hadjipavlou-Litina
Received: 3 October 2016 / Revised: 19 October 2016 / Accepted: 20 October 2016 / Published: 26 October 2016
(This article belongs to the Section Bioorganic Chemistry)
View Full-Text   |   Download PDF [803 KB, uploaded 26 October 2016]   |  

Abstract

A novel series of diethyl {4-[(5-substituted-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-methyl]-1H-1,2,3-triazol-1-yl}alkylphosphonates designed as analogues of amonafide was synthesized. All phosphonates were assessed for antiviral activity against a broad range of DNA and RNA viruses and several of them showed potency against varicella-zoster virus (VZV) [EC50 (50% effective concentration) = 27.6–91.5 μM]. Compound 16b exhibited the highest activity against a thymidine kinase-deficient (TK) VZV strain (EC50 = 27.59 μM), while 16d was the most potent towards TK+ VZV (EC50 = 29.91 μM). Cytostatic properties of the compounds 14ai17ai were studied on L1210, CEM, HeLa and HMEC-1 cell lines and most of them were slightly cytostatic for HeLa [IC50 (50% inhibitory concentration) = 29–130 µM] and L1210 cells [IC50 (50% inhibitory concentration) = 14–142 µM]. View Full-Text
Keywords: azidophosphonates; acyclonucleotides; naphthalimides; 1,2,3-triazoles; cycloaddition; antiviral; cytostatic azidophosphonates; acyclonucleotides; naphthalimides; 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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Głowacka, I.E.; Gulej, R.; Grzonkowski, P.; Andrei, G.; Schols, D.; Snoeck, R.; Piotrowska, D.G. Synthesis and the Biological Activity of Phosphonylated 1,2,3-Triazolenaphthalimide Conjugates. Molecules 2016, 21, 1420.

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