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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

✍ Scribed by Frank Seela; Rainer Gumbiowski

Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
720 KB
Volume
74
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

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.

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