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1,7‐Dideaza‐2′,3′‐dideoxyadenosine: Syntheses of Pyrrolo[2,3‐ b ]pyndine 2′,3′‐Dideoxyribofuranosides and Participation of Purine N(1) during HIV‐1 Reverse Transcriptase Inhibition
Author(s) -
Seela Frank,
Gumbiowski Rainer
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740514
Subject(s) - chemistry , deoxygenation , purine , stereochemistry , reverse transcriptase , pyridine , enzyme , medicinal chemistry , catalysis , biochemistry , rna , gene
The syntheses of 1,7‐dideaza‐2′,3′‐dideoxyadenosine ( 1 ) and related pyrrolo[2,3‐ b ]pyridine 2′,3′‐dideoxyribi and 2′,3′‐didehydro‐2′,3′‐dideoxyribonucleosides (see 2–5 ) are described. As starting materials, 2′‐deoxyribo‐nucleosides 6 or 7 were used. The 3′‐OH group was removed by Barton deoxygenation or via mesylation follow by elimination and catalytic hydrogenation. Compound 1 was also obtained from the direct glycosylation of 4‐nitro‐1 H ‐pyrrolo[2,3‐ b ]pyridine ( 17 ) with the 2,3‐dideoxyribofuranosyl chloride 18. The triphosphate 25 of 1 showed only marginal activity against HIV‐1 reverse transcriptase, indicating that purine N(1) is required for the inhibitory activity of the parent 2′,3′‐dideoxyadenosine.