About: Synthesis of fluorinated acyclic nucleoside phosphonates with 5-azacytosine base moiety

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About: Synthesis of fluorinated acyclic nucleoside phosphonates with 5-azacytosine base moiety Goto Sponge NotDistinct Permalink

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

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type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
title	Synthesis of fluorinated acyclic nucleoside phosphonates with 5-azacytosine base moiety
Creator	Andrei, Graciela Snoeck, Robert Pomeisl, Karel Pohl, Radek Kre Cmerov A, Marcela
source	Elsevier; Medline; PMC
abstract	Abstract With respect to the strong antiviral activity of (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine various types of its side chain fluorinated analogues were prepared. The title compound, (S)-1-[3-fluoro-2-(phosphonomethoxy)propyl]-5-azacytosine (FPMP-5-azaC) was synthesised by the condensation reaction of (S)-2-[(diisopropoxyphosphoryl)methoxy)-3-fluoropropyl p-toluenesulfonate with a sodium salt of 5-azacytosine followed by separation of appropriate N 1 and O 2 regioisomers and ester hydrolysis. Transformations of FPMP-5-azaC to its 5,6-dihydro-5-azacytosine counterpart, amino acid phosphoramidate prodrugs and systems with an annelated five-membered imidazole ring, i.e. imidazo [1,2-a][1,3,5]triazine derivatives were also carried out. 1-(2-Phosphonomethoxy-3,3,3-trifluoropropyl)-5-azacytosine was prepared from 5-azacytosine and trifluoromethyloxirane to form 1-(3,3,3-trifluoro-2-hydroxypropyl)-5-azacytosine which was treated with diisopropyl bromomethanephosphonate followed by deprotection of esters. Antiviral activity of all newly prepared compounds was studied. FPMP-5-azaC diisopropyl ester inhibited the replication of herpes viruses with EC50 values that were about three times higher than that of the reference anti-HCMV drug ganciclovir without displaying cytotoxicity.
has issue date	2019-09-27(xsd:dateTime)
bibo:doi	10.1016/j.tet.2019.130529
bibo:pmid	32287433
has license	els-covid
sha1sum (hex)	aabe5fd7d75d19ba4daca67de64e0b2db4a05d6e
schema:url	https://doi.org/10.1016/j.tet.2019.130529
resource representing a document's title	Synthesis of fluorinated acyclic nucleoside phosphonates with 5-azacytosine base moiety
has PubMed Central identifier	PMC7111758
has PubMed identifier	32287433
schema:publication	Tetrahedron
resource representing a document's body	covid:aabe5fd7d75d19ba4daca67de64e0b2db4a05d6e#body_text
is schema:about of	named entity 'replication' named entity '5-azaC' named entity 'prepared' named entity 'cytotoxicity' named entity 'Transformations' named entity 'prepared' named entity 'fluorinated' named entity 'nucleoside' covid:arg/aabe5fd7d75d19ba4daca67de64e0b2db4a05d6e named entity 'types' named entity '3,3,3' named entity 'synthesised' named entity 'regioisomers' named entity '5-azaC' named entity 'carried' named entity 'counterpart' named entity 'ganciclovir' named entity '5-azaC' named entity 'separation' named entity '3,3,3' named entity '3,3,3' named entity 'regioisomers' named entity 'Antiviral activity' named entity 'condensation reaction' named entity 'methoxy' named entity 'moiety' named entity 'phosphonates' named entity 'nucleoside' named entity 'acetonitrile' named entity 'chloroform' named entity 'azacitidine' named entity 'acyclovir' named entity 'inhibitory activity' named entity 'cidofovir' named entity 'triazine' named entity 'salt' named entity 'hydroxy group' named entity 'reaction conditions' named entity 'triphenylphosphine' named entity 'cytotoxic' named entity 'purine' named entity 'nucleophilic' named entity 'antiviral' named entity 'salt' named entity 'pharmacological properties' named entity 'potassium hydrogen difluoride' named entity 'ester groups' named entity 'phosphoramidate' named entity 'herpesviruses' named entity 'Column chromatography' named entity 'cleavage' named entity 'irradiation' named entity 'acyclovir' named entity 'caesium carbonate' named entity 'mmol' named entity 'magnesium sulphate' named entity 'toluene' named entity 'hydrogenated' named entity 'prodrug' named entity '5-azacytidine' named entity 'cytostatic' named entity 'human cytomegalovirus' named entity 'moiety' named entity 'mmol' named entity 'parainfluenza' named entity 'methanol' named entity 'salt' named entity 'reaction time' named entity 'fluorination' named entity 'biologically active' named entity 'deprotection' named entity 'adefovir' named entity 'ethyl acetate' named entity 'African green monkey kidney cells' named entity 'phosphonate' named entity 'ester' named entity 'Celite'

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