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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
5
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pubmed:dateCreated |
1976-8-2
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pubmed:abstractText |
Reaction of the trimethylsilyl derivative of 2,3-dihydro-6H-1,3-oxazine-2,6-dione (2, "uracil anhydride") with protected 1-O-acetylribofuranoses in the presence of stannic chloride gave the corresponding block nucleosides. 3-(2,3-5-Tri-O-2',2',2'-trichloroethoxycarbonyl-beta-d-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione (4c) thus prepared from the protected sugar 3c, 1-O-acetyl-2,3,5-tri-O-(2,2,2-trichloroethoxycarbonyl)ribofuranose, gave, on removal of the protecting groups with zinc dust,3-(beta-d-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione (1). The structure of 1 was confirmed by uv, ir, NMR, and CD spectral data and was shown to be an N nucleoside. Uracil anhydride, 2, and, to a lesser extent, its ribonucleoside 1 exert a moderate growth inhibition of mouse leukemia L5178Y, HeLa, and Novikoff hepatoma cells i- culture. Both compounds produce weak inhibition of vaccinia viral replication in HeLa cells.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
May
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
19
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
643-7
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:178870-Animals,
pubmed-meshheading:178870-Carcinoma, Hepatocellular,
pubmed-meshheading:178870-Cell Line,
pubmed-meshheading:178870-Escherichia coli,
pubmed-meshheading:178870-Leukemia, Experimental,
pubmed-meshheading:178870-Leukemia L1210,
pubmed-meshheading:178870-Liver Neoplasms,
pubmed-meshheading:178870-Mice,
pubmed-meshheading:178870-Neoplasms, Experimental,
pubmed-meshheading:178870-Oxazines,
pubmed-meshheading:178870-Rats,
pubmed-meshheading:178870-Ribonucleosides,
pubmed-meshheading:178870-Uridine,
pubmed-meshheading:178870-Vaccinia virus,
pubmed-meshheading:178870-Virus Replication
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pubmed:year |
1976
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pubmed:articleTitle |
Synthesis and biological studies of 3-(beta-D-ribofuranosyl)-2,3,-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.
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