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Keywords = azidophosphonates

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20 pages, 803 KiB  
Article
Synthesis and the Biological Activity of Phosphonylated 1,2,3-Triazolenaphthalimide Conjugates
by Iwona E. Głowacka, Rafał Gulej, Piotr Grzonkowski, Graciela Andrei, Dominique Schols, Robert Snoeck and Dorota G. Piotrowska
Molecules 2016, 21(11), 1420; https://doi.org/10.3390/molecules21111420 - 26 Oct 2016
Cited by 11 | Viewed by 5999
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 [...] Read more.
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 14a–i–17a–i 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]. Full article
(This article belongs to the Section Bioorganic Chemistry)
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19 pages, 834 KiB  
Article
Phosphonylated Acyclic Guanosine Analogues with the 1,2,3-Triazole Linker
by Iwona E. Głowacka, Graciela Andrei, Dominique Schols, Robert Snoeck and Dorota G. Piotrowska
Molecules 2015, 20(10), 18789-18807; https://doi.org/10.3390/molecules201018789 - 16 Oct 2015
Cited by 9 | Viewed by 6491
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 [...] Read more.
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. Full article
(This article belongs to the Section Organic Chemistry)
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