Synthesis and biologic activity of purine 2'-deoxy-2'-fluoro- ribonucleosides

Article abstract of DOI:10.1080/15257779408013243

The synthesis of 3,5-di-O-benzoyl-2-deoxy-2-fluoro-D-ribofuranosyl bromide (8) and its reaction with 2,6-dichloropurine by fusion and with mercuric cyanide catalysis is described. The resulting 2,6-dichloro-9-(3,5-di-O- benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine (13) was converted to the 2-fluoroadenine (16), the 2-chloroadenine (17), 2,6-diaminopurine (12), and guanine (14) nucleosides by standard procedures. These nucleosides were cytotoxic to a number of cell lines in culture. The 2-haloadenine nucleosides 16 and 17 gave modest increases in lifespan when tested against the P388 leukemia in mice.

Full text of DOI:10.1080/15257779408013243

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Synthesis and Biologic Activity of Purine
2′-Deoxy-2′-fluoro-ribonucleosides
H. Jeanette Thomas a , Kamal N. Tiwari a , Sarah Jo Clayton a , John
A. Secrist III a & John A. Montgomery a
a Southern Research Institute, P. O. Box 55305, Birmingham,
Alabama, 35255-5305
Version of record first published: 23 Sep 2006.
To cite this article: H. Jeanette Thomas , Kamal N. Tiwari , Sarah Jo Clayton , John A. Secrist
III & John A. Montgomery (1994): Synthesis and Biologic Activity of Purine 2′-Deoxy-2′-fluoro-
ribonucleosides, Nucleosides and Nucleotides, 13:1-3, 309-323
To link to this article: http://dx.doi.org/10.1080/15257779408013243
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