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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
3
|
pubmed:dateCreated |
1980-6-25
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pubmed:abstractText |
The synthesis of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido[2,3-d]pyrimidine (BW301U, 7) by a route that has general applicability to the preparation of many 6-(substituted benzyl)-5-methylpyrido[2,3-d]pyrimidines is described. The key intermediate, 2,4-diamino-7,8-dihydro-6-(2,5-dimethoxybenzyl)-5-methyl-7-oxopyrido[2,3-d]pyrimidine (4), is converted to the 7-chloro compound 5 by treatment with a 1:1 complex of N,N-dimethylformamide--thionyl chloride, and 5 is hydrogenolyzed with palladium on charcoal in the presence of potassium hydroxide to yield 7. BW301U is a potent lipid-soluble inhibitor of mammalian dihydrofolate reductase and has significant activity against the Walker 256 carcinosarcoma in rats.
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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 |
Mar
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
23
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
327-9
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:6928967-Animals,
pubmed-meshheading:6928967-Antineoplastic Agents,
pubmed-meshheading:6928967-Carcinoma 256, Walker,
pubmed-meshheading:6928967-Cell Division,
pubmed-meshheading:6928967-Folic Acid Antagonists,
pubmed-meshheading:6928967-Humans,
pubmed-meshheading:6928967-Leukemia, Myeloid,
pubmed-meshheading:6928967-Male,
pubmed-meshheading:6928967-Methotrexate,
pubmed-meshheading:6928967-Pyrimidines,
pubmed-meshheading:6928967-Rats
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pubmed:year |
1980
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pubmed:articleTitle |
Synthesis and antitumor activity of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido[2,3-d]pyrimidine.
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pubmed:publicationType |
Journal Article,
In Vitro
|