Linked Life Data

3585903

Source:http://linkedlifedata.com/resource/pubmed/id/3585903

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
6
pubmed:dateCreated
1987-7-9
pubmed:abstractText
2-Deoxy-beta-D-ribo-hexopyranosyl nucleosides with adenine (2), hypoxanthine (17), guanine (23), cytosine (13), and uracil (7) as the aglycon were synthesized by the Lewis-acid catalyzed condensation of an appropriate trimethylsilylated heterocyclic base and 2-deoxy-1,3,4,6-tetrakis-O-(4-nitrobenzoyl)-beta-D-ribo-hexopyranose+ ++ (5) to provide the desired beta anomers in good yield. When the synthesis of 7 via an SN2 displacement was attempted by reaction between silylated uracil and 2-deoxy-3,4,6-tris-O-(4-nitrobenzoyl)-alpha-D-ribo-hexopyranosyl bromide (8), the major product, 1-(2-deoxy-3,4,6-tris-O-(4-nitrobenzoyl)-alpha-D-ribo-hexopyranosyl)-2,4 - pyrimidinedione (9), had retained the alpha configuration at the anomeric carbon. The structures of both anomers of 1-(2-deoxy-D-ribo-hexopyranosyl)-2,4-pyrimidinedione were assigned by single-crystal X-ray methods. The anomeric configuration and conformation of other nucleosides were determined by proton magnetic resonance analysis of the 4-nitrobenzoylated nucleosides. Nucleoside 6'-monophosphates of 7, 13, and 2 and the 4',6'-cyclic monophosphate of 2 were also prepared. All 2'-deoxy-D-ribo-hexopyranosyl nucleosides and 6'-monophosphate derivatives were tested in vitro for antiviral and antitumor activity. The guanosine analogue 23 was moderately active against HSV-2 virus. The UMP analogue, 1-(2-deoxy-6-O-phosphono-beta-D-ribo-hexopyranosyl) -2,4-pyrimidinedione (28), demonstrated moderate activity against HSV-2 and parainfluenza 3 virus and was also active against L1210 (ID50 = 39 microM) and P388 (ID50 = 33 microM) leukemic cell lines. Two compounds, 6-amino-9-(2-deoxy-beta-D-ribo-hexopyranosyl)purine (2) and 9-(2-deoxy-beta-D-ribo-hexopyranosyl)-2,6-diaminopurine (24), were substrates for adenosine deaminase (EC 3.5.4.4) with Km values of 57 and 90 microM, respectively. 6-Amino-7-(2-deoxy-beta-D-ribo-hexopyranosyl)purine, 18, was a competitive inhibitor of ADase (Ki = 0.1 mM).
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jun
pubmed:issn
0022-2623
pubmed:author
pubmed:issnType
Print
pubmed:volume
30
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
1044-54
pubmed:dateRevised
2009-11-19
pubmed:meshHeading
pubmed:year
1987
pubmed:articleTitle
Synthesis, structure, and biological activity of certain 2-deoxy-beta-D-ribo-hexopyranosyl nucleosides and nucleotides.
pubmed:publicationType
Journal Article