Synthesis of some tricyclic nucleosides related to the Y base of tRNA

Anderson, Gary L.; Rizkalla, Boshra H.; Broom, Arthur D.

doi:10.1021/jo00921a018

Cited by 14 publications

(2 citation statements)

References 4 publications

(9 reference statements)

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“…Chemistry. The key starting material for the requisite polynucleotide and oligonucleotide precursors was 5H (7 H )-9-oxo-3-(β- d -ribofuranosyl)-1,2,4-triazolo[2,3- a ]purine ( 6 ), which was prepared as previously described by cyclization of 1-aminoguanosine using phosphoryl chloride in DMF.…”

Section: Resultsmentioning

confidence: 99%

Antiviral Oligo- and Polyribonucleotides Containing Selected Triazolo[2,3-a]purines

et al. 1998

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Several amphipathic (hydrophobic base, hydrophilic backbone) polyribonucleotides have recently been shown to have potent antiviral activity against HIV and human cytomegalovirus (HCMV). The working hypothesis developed during these studies was that the ability to form an ordered, non-hydrogen-bonded array in solution was an important criterion for activity. To explore further the role of structure and molecular size on the inhibition of virus replication, one new polynucleotide and two 32-mer oligonucleotides based on the triazolo[2,3-a]purine ring system have now been prepared. High-molecular-weight polynucleotide 4a (PTPR) and sulfur-containing 32-mer 5b (TTPR) were moderately active against HIV but showed greater potency against HDMV than ganciclovir. Both 4a and 5b gave clear evidence of cooperative melting behavior, whereas inactive 32-mer 5a showed no such behavior.

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Section: Resultsmentioning

confidence: 99%

Antiviral Oligo- and Polyribonucleotides Containing Selected Triazolo[2,3-a]purines

et al. 1998

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“…Treatment of 4 with 1 equiv of POCl 3 in DMF (Vilsmeier−Haack reagent) at ambient temperature gave predominantly 6-amino-3-(2,3,5-tri- O -benzoyl-β- d -ribofuranosyl)purine-2-one ( 5a ) . One might expect a mixture of 5a and its isomer 7 from the reaction, but the major product isolated was 5a in 85% yield.…”

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confidence: 99%