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PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
6
pubmed:dateCreated
1980-9-26
pubmed:abstractText
The synthesis and cytostatic activity of several chloromethyl- and iodomethylpyrazole nucleosides are described. Glycosylation of ethyl 3(5)-(chloromethyl)pyrazole-5(3)-carboxylate (3) and 3(5)-(chloromethyl)pyrazole-5(3)-carboxamide (4) with poly(O-acetylated) sugars via an acid-catalyzed fusion method gave the corresponding 3-(chloromethyl)-5-carboxylate and 3-(chloromethyl)-5-carboxamide substituted nucleosides 7 and 9, respectively. From the reaction of 4 with tetra-O-acetyl-beta-D-ribofuranose, the 5-(chloromethyl)-3-carboxamide-substituted derivative 11 was also obtained. Reaction of 7, 9, and 11 with sodium iodide in acetone provided the related iodomethylpyrazole nucleosides 8, 10, and 12. In general, chloromethyl-substituted nucleotides showed moderate activities against HeLa cells, while all the corresponding iodomethyl derivatives exhibited high activities. Some of these latter compounds increased the life span of mice bearing ECA tumor.
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
23
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
657-60
pubmed:dateRevised
2004-11-17
pubmed:meshHeading
pubmed:year
1980
pubmed:articleTitle
Alkylating nucleosides. 4. Synthesis and cytostatic activity of chloro- and iodomethylpyrazole nucleosides.
pubmed:publicationType
Journal Article