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Nucleotides. Part. XXXII. Synthesis of 2′–5′ Connected oligonucleotides. Prodrugs for antiviral and antitumoral nucleosides

✍ Scribed by Piet Herdewijn; Ramamurthy Charubala; Erik De Clercq; Wolfgang Pfleiderer

Publisher: John Wiley and Sons
Year: 1989
Tongue: German
Weight: 703 KB
Volume: 72
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19890720811

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✦ Synopsis

The cytotoxically and antivirally active compounds bvU, (l), flu, (4). acyclovir (7), and A, (12) have chemically been combined with the appropriately protected (2-5')diadenylate 20 by the phosphotriester approach to give the 2'-5' oligonucleotide trimers 21-24. The deprotection of the various blocking groups by chemical means afforded the 2-5' trimers 25-28, which can be regarded as a new type of a potential prodrug form delivering nncleotides to the targets inside cells. In an analogous series of reactions, 9-(3'-azido-3'-deoxy-~-~-xylofura-nosy1)adenine was coupled with 7 to the 2-5' trimer 31. The antiviral screening of the oligonucleotides 2 5 2 7 and 31 showed biological activities closely related to the parent nucleosides, possibly indicating their release by enzymatic cleavage of the oligomers.

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