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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
2
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pubmed:dateCreated |
1986-4-4
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pubmed:abstractText |
Bromination of 3,4-di-O-acetyl-L-rhamnal (7) and subsequent glycosidic coupling under Koenigs-Knorr conditions with daunomycinone gave a mixture of three compounds having the beta-L-gluco (10), alpha-L-gluco (11), and alpha-L-manno (12) configurations. Analogous bromination of 3,4-di-O-acetyl-L-fucal (13) followed by coupling with daunomycinone gave a mixture of three glycosides having the beta-L-galacto (16), alpha-L-galacto (17), and alpha-L-talo (18) configurations. Chlorination of 7 and coupling with daunomycinone in the presence of silver triflate gave products having the alpha-L-gluco (21) and alpha-L-manno (22) configurations, whereas 13, under similar conditions, gave only one stereoisomeric product, that having the alpha-L-galacto (24) configuration. Compounds 12 and 22 showed high in vivo activity in the P-388 lymphocytic leukemia assay.
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pubmed:grant | |
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 |
Dec
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pubmed:issn |
0008-6215
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
1
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pubmed:volume |
144
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
305-15
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:4092209-Animals,
pubmed-meshheading:4092209-Antibiotics, Antineoplastic,
pubmed-meshheading:4092209-Daunorubicin,
pubmed-meshheading:4092209-Indicators and Reagents,
pubmed-meshheading:4092209-Leukemia P388,
pubmed-meshheading:4092209-Magnetic Resonance Spectroscopy,
pubmed-meshheading:4092209-Mice,
pubmed-meshheading:4092209-Structure-Activity Relationship
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pubmed:year |
1985
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pubmed:articleTitle |
Synthesis and antitumor activity of 2'-bromo- and 2'-chloro-3'-acetoxy-3'-deaminodaunorubicin analogs.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.
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