P. Alexander, A. Holý, M. Buděšínský
2000
Citations
0
Influential Citations
1
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Journal
Collection of Czechoslovak Chemical Communications
Abstract
Reaction of 9-benzyl-6-{[(dimethylamino)methylidene]amino}purin-2(3 H )-one ( 7 ) with ethylene carbonate gave a mixture of 9-benzyl-2-(2-hydroxyethoxy)purin-6-amine ( 10 ) and 2-amino-9-benzyl-3-(2-hydroxyethyl)purin-2(3 H )-one ( 11 ). This mixture reacted with diisopropyl (tosyloxymethyl)phosphonate in the presence of NaH followed by catalytic hydrogenation and bromotrimethylsilane treatment to afford isomeric 6-amino-3-[2-(phosphonomethoxy)ethyl]purin-2(3 H )-one ( 3 ) and 2-[2-(phosphonomethoxy)ethoxy]purin- 6-amine ( 15 ). Similar treatment of compound 7 with tritylglycidol gave two isomeric 2-hydroxy-3-(trityloxy)propyl derivatives 18 , 20 which were subsequently condensed with diisopropyl (tosyloxymethyl)phosphonate to afford protected diester intermediates 21 and 22 ; these compounds were transformed by hydrogenolysis and ester cleavage with bromotrimethylsilane to the isomeric 6-amino-3-[3-hydroxy-2-(phosphonomethoxy)propyl]- purin-2(3 H )-one ( 2 ) and 2-[3-hydroxy-2-(phosphonomethoxy)propoxy]purin-6-amine ( 24 ). None of the free phosphonates 2 , 3 , 15 or 24 exhibited any antiviral or cytostatic activity.