Bicyclic Nucleoside Inhibitors of Varicella—Zoster Virus: Synthesis and Biological Evaluation of 2′,3′-Dideoxy-3′-fluoro and 2′-Deoxy-xylo Derivatives

ChemInform ◽  
2004 ◽  
Vol 35 (5) ◽  
Author(s):  
A. Carangio ◽  
C. McGuigan ◽  
G. Andrei ◽  
R. Snoeck ◽  
E. De Clercq ◽  
...  
Keyword(s):  
Varicella Zoster Virus ◽  
Biological Evaluation ◽  
Varicella Zoster ◽  
Nucleoside Inhibitors ◽  
Synthesis And Biological Evaluation

Synthesis and biological evaluation of 5-(alkyn-1-yl)-1-(p-toluenesulfonyl)uracil derivatives

2006 ◽  
Vol 84 (4) ◽  
pp. 580-586 ◽  
Author(s):  
Zlatko Janeba ◽  
Jan Balzarini ◽  
Graciela Andrei ◽  
Robert Snoeck ◽  
Erik De Clercq ◽  
...  
Keyword(s):  
Varicella Zoster Virus ◽  
Human Cytomegalovirus ◽  
Biological Evaluation ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Pyrimidine Derivatives ◽  
Varicella Zoster ◽  
Uracil Derivatives ◽  
Synthesis And Biological Evaluation

Sonogashira coupling of 5-iodouracil (2) and trimethylsilylacetylene gave 5-(trimethylsilylethynyl)uracil (3), which was deprotected to give 5-ethynyluracil (4). Copper(I)-catalyzed cyclization of 4 gave furo[2,3-d]pyrimidin-2(3H)-one (5). Tosylation of 2 and 4 gave the 1-(p-toluenesulfonyl) derivatives 6 and 7, respectively. The tosylated compound 6 and trimethylsilylacetylene did not undergo Sonogashira coupling, and copper(I)-catalyzed cyclization of 7 did not occur. Coupling of 2 with several terminal alkynes gave 5-(alkyn-1-yl)uracil derivatives (9), which underwent tosylation to produce the targeted 5-(alkyn-1-yl)-1-(p-toluenesulfonyl)uracil compounds (11). Copper(I)-catalyzed cyclization of 9 gave the respective furopyrimidines (10) in low yields. Again, cyclization did not occur with the tosyl derivatives (11). Activity against varicella-zoster virus (VZV) was observed with longer-chain analogues of 9 and 11, and compound 7 showed activity against human cytomegalovirus (HCMV) at near cytotoxic levels.Key words: antiviral screening, furo[2,3-d]pyrimidin-2(3H)-one derivatives, Sonogashira coupling, 1-(p-toluenesulfonyl)pyrimidine derivatives.

Bicyclic Nucleoside Inhibitors of Varicella—Zoster Virus: 5′-Chloro and 3′-Chloro Derivatives

ChemInform ◽  
2004 ◽  
Vol 35 (5) ◽  
Author(s):  
G. Luoni ◽  
C. McGuigan ◽  
G. Andrei ◽  
R. Snoeck ◽  
E. De Clercq ◽  
...  
Keyword(s):  
Varicella Zoster Virus ◽  
Varicella Zoster ◽  
Chloro Derivatives ◽  
Nucleoside Inhibitors

Bicyclic Nucleoside Inhibitors of Varicella—Zoster Virus: The Effect of Branching in the p-Alkylphenyl Side Chain.

ChemInform ◽  
2006 ◽  
Vol 37 (4) ◽  
Author(s):  
Giovanna Luoni ◽  
Christopher McGuigan ◽  
Graciela Andrei ◽  
Robert Snoeck ◽  
Erik De Clercq ◽  
...  
Keyword(s):  
Varicella Zoster Virus ◽  
Side Chain ◽  
Varicella Zoster ◽  
Nucleoside Inhibitors

Bicyclic Nucleoside Inhibitors of Varicella-Zoster Virus: 5′-Chloro and 3′-Chloro Derivatives

2003 ◽  
Vol 22 (5-8) ◽  
pp. 931-933 ◽  
Author(s):  
G. Luoni ◽  
C. McGuigan ◽  
G. Andrei ◽  
R. Snoeck ◽  
E. De Clercq ◽  
...  
Keyword(s):  
Varicella Zoster Virus ◽  
Varicella Zoster ◽  
Chloro Derivatives ◽  
Nucleoside Inhibitors

Bicyclic nucleoside inhibitors of Varicella–Zoster virus: The effect of branching in the p-alkylphenyl side chain

2005 ◽  
Vol 15 (16) ◽  
pp. 3791-3796 ◽  
Author(s):  
Giovanna Luoni ◽  
Christopher McGuigan ◽  
Graciela Andrei ◽  
Robert Snoeck ◽  
Erik De Clercq ◽  
...  
Keyword(s):  
Varicella Zoster Virus ◽  
Side Chain ◽  
Varicella Zoster ◽  
Nucleoside Inhibitors
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