About: Acyclic nucleoside phosphonates containing the amide bond

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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
has title	Acyclic nucleoside phosphonates containing the amide bond
Creator	Schols, Dominique Andrei, Graciela Głowacka, Iwona Piotrowska, Dorota Snoeck, • Wróblewski, Andrzej
Source	Medline; PMC
abstract	ABSTRACT: To study the influence of a linker rigidity and donor–acceptor properties, the P–CH(2)–O–CHR– fragment in acyclic nucleoside phosphonates (e.g., acyclovir, tenofovir) was replaced by the P–CH(2)–HN–C(O)– residue. The respective phosphonates were synthesized in good yields by coupling the straight chain of ω-aminophosphonates and nucleobase-derived acetic acids with EDC. Based on the (1)H and (13)C NMR data, the unrestricted rotation within the methylene and 1,2-ethylidene linkers in phosphonates from series a and b was confirmed. For phosphonates containing 1,3-propylidene (series c) fragments, antiperiplanar disposition of the bulky O,O-diethylphosphonate and substituted amidomethyl groups was established. The synthesized ANPs P–X–HNC(O)–CH(2)B (X = CH(2), CH(2)CH(2), CH(2)CH(2)CH(2), CH(2)OCH(2)CH(2)) appeared inactive in antiviral assays against a wide variety of DNA and RNA viruses at concentrations up to 100 μM while marginal antiproliferative activity (L1210 cells, IC(50) = 89 ± 16 μM and HeLa cells, IC(50) = 194 ± 19 μM) was noticed for the analog derived from (5-fluorouracyl-1-yl)acetic acid and O,O-diethyl (2-aminoethoxy)methylphosphonate. GRAPHICAL ABSTRACT: [Image: see text]
has issue date	2016-10-26(xsd:dateTime)
bibo:doi	10.1007/s00706-016-1848-x
bibo:pmid	27881885
has license	cc-by
sha1sum (hex)	4f2e6240097fc7f8699ec07c84d37bbc8a15310c
schema:url	https://doi.org/10.1007/s00706-016-1848-x
resource representing a document's title	Acyclic nucleoside phosphonates containing the amide bond
has PubMed Central identifier	PMC5101293
has PubMed identifier	27881885
schema:publication	Monatsh Chem
resource representing a document's body	covid:4f2e6240097fc7f8699ec07c84d37bbc8a15310c#body_text
is schema:about of	named entity 'analog' named entity 'acyclovir' named entity 'antiperiplanar' named entity 'amide bond' named entity 'CONTAINING' named entity 'DONOR' named entity 'DISPOSITION' named entity 'ANTIPROLIFERATIVE ACTIVITY' named entity 'UNRESTRICTED' named entity 'DNA' named entity 'AMINOPHOSPHONATES' named entity 'ANALOG' named entity 'ETHYLIDENE' named entity 'ROTATION' named entity 'ACETIC ACIDS' named entity 'BULKY' named entity 'FRAGMENTS' named entity 'RESIDUE' named entity 'NUCLEOBASE' named entity 'ACID' named entity 'GOOD' named entity 'ESTABLISHED' named entity 'COUPLING' named entity 'STUDY' named entity 'ACYCLOVIR' named entity 'GROUPS' named entity 'VARIETY' named entity 'ACCEPTOR' named entity 'CELLS' named entity 'UP TO' named entity 'MARGINAL' named entity 'PROPERTIES' named entity 'ACYCLIC' named entity '100' named entity 'CONCENTRATIONS' named entity 'LINKER' named entity 'HNC' named entity 'SYNTHESIZED' named entity 'EDC' named entity 'RNA VIRUSES' named entity 'PHOSPHONATES' named entity 'DERIVED' named entity 'PHOSPHONATES' named entity 'HELA CELLS' named entity 'ANTIVIRAL' named entity 'STRAIGHT' named entity 'OCH' named entity 'NMR DATA' named entity '1 H' named entity 'FRAGMENT' named entity 'WIDE' named entity 'RIGIDITY' named entity 'REPLACED BY' named entity 'PROPYLIDENE' named entity 'AMIDE BOND' named entity 'CHAIN' named entity 'NUCLEOSIDE' named entity 'CONTAINING' named entity '282' named entity 'SERIES' named entity 'TENOFOVIR' named entity 'BASED' named entity 'ACYCLIC' named entity 'NUCLEOSIDE' named entity 'METHYLENE' named entity 'CHR' named entity 'INACTIVE' named entity 'INFLUENCE' named entity 'CONFIRMED' covid:arg/4f2e6240097fc7f8699ec07c84d37bbc8a15310c named entity 'linker' named entity 'antiproliferative' named entity 'good' named entity 'DNA' named entity 'HeLa cells' named entity 'fragments'

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