Acyclic nucleoside phosphonates containing the amide bond
Identifieur interne : 001011 ( Main/Exploration ); précédent : 001010; suivant : 001012Acyclic nucleoside phosphonates containing the amide bond
Auteurs : Iwona E. Głowacka [Pologne] ; Dorota G. Piotrowska [Pologne] ; Graciela Andrei [Belgique] ; Dominique Schols [Belgique] ; Robert Snoeck [Belgique] ; Andrzej E. Wr Blewski [Pologne]Source :
- Monatshefte Fur Chemie [ 0026-9247 ] ; 2016.
Abstract
To study the influence of a linker rigidity and donor–acceptor properties, the P–CH2–
Url:
DOI: 10.1007/s00706-016-1848-x
PubMed: 27881885
PubMed Central: 5101293
Affiliations:
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- to stream Main, to step Curation: 001011
Le document en format XML
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<series><title level="j">Monatshefte Fur Chemie</title>
<idno type="ISSN">0026-9247</idno>
<idno type="eISSN">1434-4475</idno>
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<front><div type="abstract" xml:lang="en"><sec><title>Abstract</title>
<p id="Par1">To study the influence of a linker rigidity and donor–acceptor properties, the P–CH<sub>2</sub>
–<bold>O–CHR</bold>
– fragment in acyclic nucleoside phosphonates (e.g., acyclovir, tenofovir) was replaced by the P–CH<sub>2</sub>
–<bold>HN–C(O)</bold>
– residue. The respective phosphonates were synthesized in good yields by coupling the straight chain of <italic>ω</italic>
-aminophosphonates and nucleobase-derived acetic acids with EDC. Based on the <sup>1</sup>
H and <sup>13</sup>
C NMR data, the unrestricted rotation within the methylene and 1,2-ethylidene linkers in phosphonates from series <bold>a</bold>
and <bold>b</bold>
was confirmed. For phosphonates containing 1,3-propylidene (series <bold>c</bold>
) fragments, antiperiplanar disposition of the bulky <italic>O</italic>
,<italic>O</italic>
-diethylphosphonate and substituted amidomethyl groups was established. The synthesized ANPs P–X–HNC(O)–CH<sub>2</sub>
B (X = CH<sub>2</sub>
, CH<sub>2</sub>
CH<sub>2</sub>
, CH<sub>2</sub>
CH<sub>2</sub>
CH<sub>2</sub>
, CH<sub>2</sub>
OCH<sub>2</sub>
CH<sub>2</sub>
) 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<sub>50</sub>
= 89 ± 16 μM and HeLa cells, IC<sub>50</sub>
= 194 ± 19 μM) was noticed for the analog derived from (5-fluorouracyl-1-yl)acetic acid and <italic>O</italic>
,<italic>O</italic>
-diethyl (2-aminoethoxy)methylphosphonate.</p>
</sec>
<sec><title>Graphical abstract</title>
<p id="Par2"><graphic position="anchor" xlink:href="706_2016_1848_Figa_HTML" id="MO1"></graphic>
</p>
</sec>
</div>
</front>
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<li>Pologne</li>
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<settlement><li>Louvain</li>
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