Synthesis of Potential Purinoceptor Antagonists: Application of P1-tBu Phosphazene Base for Alkylation of Adenine in Solution and on Solid Phase

Alkylation of adenine in solution and on solid phase was accelerated by phosphazene base P1-tBu compared to mineral bases. The reactions in solution afforded regioselectively the appropriate N9-alkylated adenines with high preparative yields while the reaction with polystyrene resin-bound N-bromoace...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2006-01, Vol.25 (2), p.141-157
Main Authors: Enkvist, Erki, Raidaru, Gerda, Uri, Asko, Patel, Roshni, Redick, Catherine, Boyer, José L., Subbi, Juhan, Tammiste, Indrek
Format: Article
Language:English
Subjects:
Adenine - analogs & derivatives
Adenine - chemistry
Adenine - pharmacology
Adenine alkylation
Alkylation
Aziridines - chemistry
Humans
Nucleotide analog
Phosphazene base
Phosphoranes - chemistry
Phosphoranes - pharmacology
Platelet Aggregation Inhibitors - pharmacology
Polystyrenes - chemistry
Purinergic Antagonists
Solid phase synthesis
Solutions - chemistry
Stereoisomerism
Time Factors
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Summary:Alkylation of adenine in solution and on solid phase was accelerated by phosphazene base P1-tBu compared to mineral bases. The reactions in solution afforded regioselectively the appropriate N9-alkylated adenines with high preparative yields while the reaction with polystyrene resin-bound N-bromoacetylated peptides gave three regioisomers (alkylated at the N9, N7, and N3 position of adenine) in a 4:2:1 molar ratio. Ten novel nonphosphate nucleotide analogues were tested in an ADP-induced platelet aggregation assay.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770500446857