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Syntheses of Pyrrolo[2,3-d]pyrimidine 2′,3′-Dideoxyribonucleosides Related to 2′,3′-Dideoxyadenosine and 2′,3′-Dideoxyguanosine and Inhibitory Activity of 5′-Triphosphates on HIV-1 Reverse Transcriptase

✍ Scribed by Frank Seela; Heinz-Peter Muth; Angelika Röling

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

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✦ Synopsis

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The synthesis of 4-chloropyrrolo[2,3-d]pyrimidine and 2-amino-4-chloropyrrolo[2,3-d]pyrimidine a -D-and ~-~-2',3'-dideoxyribonucleosides 6a, b and 7a, b is described (Scheme 1). Glycosylation of the pyrrolo[2,3-d]pyrimidinyl anions of la, b with in situ prepared 2,3-dideoxy-a /B-D-glycero-pentofuranosyl chloride (2) was regioselective but afforded anomeric mixtures of the 2',3'-dideoxyribonucleosides 3a/4a and 3b/4b, respectively. The glycosylation products were deprotected and subjected to nucleophilic displacement yielding various pyrrolo[2,3-d]pyrimidine 2',3'-deoxyribonucleosides related to 2',3'-dideoxyadenosine and 2',3'-dideoxyguanosine. One-pot phosphorylation gave the corresponding triphosphates. Some of them are strong inhibitors of HIV-1 reverse trauscriptase, similar to corresponding purine 2',3'-dideoxynucleotides, but exhibit a better selectivity index in comparison to DNA polymerases. According to that, the N(7) of the purine moiety is not an essential binding position of ddATP or ddGTP at the active centre of HIV-1 reverse transcriptase.

') The IUPAC-IUB-recommended abbreviation of this compound is Td33' az (T = ribosylthymine and not thymidine, which is 2'-deoxyribosylthymine, hence Td).

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