About: Synthesis of 3-fluoro-6-S-(2-S-pyridyl) nucleosides as potential lead cytostatic agents

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About: Synthesis of 3-fluoro-6-S-(2-S-pyridyl) nucleosides as potential lead cytostatic agents Goto Sponge NotDistinct Permalink

An Entity of Type : schema:ScholarlyArticle, within Data Space : covidontheweb.inria.fr associated with source document(s)

Attributes	Values
type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
has title	Synthesis of 3-fluoro-6-S-(2-S-pyridyl) nucleosides as potential lead cytostatic agents
Creator	Balzarini, Jan Komiotis, Dimitri Manta, Stella Tsoukala, Evangelia Tzioumaki, Niki Riga, Alexandra
Source	Elsevier; Medline; PMC
abstract	Abstract The 3-deoxy-3-fluoro-6-S-(2-S-pyridyl)-6-thio-β-d-glucopyranosyl nucleoside analogs 7 were prepared via two facile synthetic routes. Their precursors, 3-fluoro-6-thio-glucopyranosyl nucleosides 5a-e, were obtained by the sequence of deacetylation of 3-deoxy-3-fluoro-β-d-glucopyranosyl nucleosides 2a-e, selective tosylation of the primary OH of 3 and finally treatment with potassium thioacetate. The desired thiolpyridine protected analogs 7a-c,f,g were obtained by the sequence of deacetylation of 5a-c followed by thiopyridinylation and/or condensation of the corresponding heterocyclic bases with the newly synthesized peracetylated 6-S-(2-S-pyridyl) sugar precursor 13, which was obtained via a novel synthetic route from glycosyl donor 12. None of the compounds 6 and 7 showed antiviral activity, but the 5-fluorouracil derivative 7c and particularly the uracil derivative 7b were endowed with an interesting and selective cytostatic action against a variety of murine and human tumor cell cultures.
has issue date	2010-12-31(xsd:dateTime)
bibo:doi	10.1016/j.bioorg.2010.08.001
bibo:pmid	20817215
has license	els-covid
sha1sum (hex)	fdcf5c9671ca7f461b4b7281d11eeafde8101cb0
schema:url	https://doi.org/10.1016/j.bioorg.2010.08.001
resource representing a document's title	Synthesis of 3-fluoro-6-S-(2-S-pyridyl) nucleosides as potential lead cytostatic agents
has PubMed Central identifier	PMC7112006
has PubMed identifier	20817215
schema:publication	Bioorganic Chemistry
resource representing a document's body	covid:fdcf5c9671ca7f461b4b7281d11eeafde8101cb0#body_text
is schema:about of	named entity 'PRECURSORS' named entity 'NUCLEOSIDE ANALOGS' named entity 'PRECURSOR' named entity 'SELECTIVE' named entity 'HUMAN' named entity 'NEWLY' named entity 'MURINE' named entity 'TREATMENT' named entity 'DEOXY' named entity 'FOLLOWED BY' named entity 'VARIETY' named entity 'selective' named entity 'endowed' named entity 'synthetic routes' named entity 'action' named entity 'FLUORO' named entity 'SYNTHESIS' named entity '282' named entity 'SYNTHETIC' named entity 'DEACETYLATION' covid:arg/fdcf5c9671ca7f461b4b7281d11eeafde8101cb0 named entity 'NUCLEOSIDES' named entity 'LEAD' named entity 'POTASSIUM' named entity 'PREPARED' named entity 'THEIR' named entity 'THIO' named entity 'BASES' named entity 'ROUTE' named entity 'URACIL DERIVATIVE' named entity 'SUGAR' named entity 'INTERESTING' named entity 'TUMOR CELL' named entity 'POTENTIAL' named entity 'GLYCOSYL DONOR' named entity '282' named entity 'FLUORO' named entity 'TOSYLATION' named entity 'ACTION' named entity 'PRIMARY' named entity 'CELL CULTURES' named entity 'CYTOSTATIC' named entity 'CYTOSTATIC AGENTS' named entity '5-FLUOROURACIL' named entity 'ANTIVIRAL ACTIVITY' named entity 'BUT' named entity 'NUCLEOSIDES' named entity 'NOVEL' named entity 'D-GLUCOPYRANOSYL' named entity 'OBTAINED' named entity 'OBTAINED BY' named entity 'ANALOGS' named entity 'ROUTES' named entity 'DERIVATIVE' named entity 'CONDENSATION' named entity 'THIOACETATE' named entity 'SEQUENCE' named entity 'derivative' named entity 'synthesized' named entity 'antiviral' named entity 'None' named entity 'human' named entity 'fluoro' named entity 'deacetylation' named entity 'thio' named entity 'antiviral activity' named entity 'synthetic routes' named entity 'synthetic route' named entity 'nucleosides' named entity 'heterocyclic' named entity 'sugar' named entity 'thio' named entity 'tosylation' named entity 'nucleosides' named entity 'deoxy' named entity 'glucopyranosyl'

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