Acyclic nucleoside phosphonates containing the amide bond
Identifieur interne : 000309 ( Pmc/Curation ); précédent : 000308; suivant : 000310Acyclic 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
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PMC:5101293Le document en format XML
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<author><name sortKey="Glowacka, Iwona E" sort="Glowacka, Iwona E" uniqKey="Glowacka I" first="Iwona E." last="Głowacka">Iwona E. Głowacka</name>
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<author><name sortKey="Piotrowska, Dorota G" sort="Piotrowska, Dorota G" uniqKey="Piotrowska D" first="Dorota G." last="Piotrowska">Dorota G. Piotrowska</name>
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<author><name sortKey="Wr Blewski, Andrzej E" sort="Wr Blewski, Andrzej E" uniqKey="Wr Blewski A" first="Andrzej E." last="Wr Blewski">Andrzej E. Wr Blewski</name>
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<series><title level="j">Monatshefte Fur Chemie</title>
<idno type="ISSN">0026-9247</idno>
<idno type="eISSN">1434-4475</idno>
<imprint><date when="2016">2016</date>
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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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<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Monatsh Chem</journal-id>
<journal-id journal-id-type="iso-abbrev">Monatsh. Chem</journal-id>
<journal-title-group><journal-title>Monatshefte Fur Chemie</journal-title>
</journal-title-group>
<issn pub-type="ppub">0026-9247</issn>
<issn pub-type="epub">1434-4475</issn>
<publisher><publisher-name>Springer Vienna</publisher-name>
<publisher-loc>Vienna</publisher-loc>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">27881885</article-id>
<article-id pub-id-type="pmc">5101293</article-id>
<article-id pub-id-type="publisher-id">1848</article-id>
<article-id pub-id-type="doi">10.1007/s00706-016-1848-x</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Original Paper</subject>
</subj-group>
</article-categories>
<title-group><article-title>Acyclic nucleoside phosphonates containing the amide bond</article-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Głowacka</surname>
<given-names>Iwona E.</given-names>
</name>
<xref ref-type="aff" rid="Aff1">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Piotrowska</surname>
<given-names>Dorota G.</given-names>
</name>
<xref ref-type="aff" rid="Aff1">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Andrei</surname>
<given-names>Graciela</given-names>
</name>
<xref ref-type="aff" rid="Aff2">2</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Schols</surname>
<given-names>Dominique</given-names>
</name>
<xref ref-type="aff" rid="Aff2">2</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Snoeck</surname>
<given-names>Robert</given-names>
</name>
<xref ref-type="aff" rid="Aff2">2</xref>
</contrib>
<contrib contrib-type="author" corresp="yes"><name><surname>Wróblewski</surname>
<given-names>Andrzej E.</given-names>
</name>
<address><email>andrzej.wroblewski@umed.lodz.pl</email>
</address>
<xref ref-type="aff" rid="Aff1">1</xref>
</contrib>
<aff id="Aff1"><label>1</label>
<institution-wrap><institution-id institution-id-type="GRID">grid.8267.b</institution-id>
<institution-id institution-id-type="ISNI">0000000121653025</institution-id>
<institution>Bioorganic Chemistry Laboratory, Faculty of Pharmacy,</institution>
<institution>Medical University of Lodz,</institution>
</institution-wrap>
Muszyńskiego 1, 90-151 Lodz, Poland</aff>
<aff id="Aff2"><label>2</label>
<institution-wrap><institution-id institution-id-type="GRID">grid.5596.f</institution-id>
<institution-id institution-id-type="ISNI">0000000106687884</institution-id>
<institution>Rega Institute for Medical Research,</institution>
<institution>KU Leuven,</institution>
</institution-wrap>
Minderbroedersstraat 10, 3000 Louvain, Belgium</aff>
</contrib-group>
<pub-date pub-type="epub"><day>26</day>
<month>10</month>
<year>2016</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>26</day>
<month>10</month>
<year>2016</year>
</pub-date>
<pub-date pub-type="ppub"><year>2016</year>
</pub-date>
<volume>147</volume>
<issue>12</issue>
<fpage>2163</fpage>
<lpage>2177</lpage>
<history><date date-type="received"><day>7</day>
<month>6</month>
<year>2016</year>
</date>
<date date-type="accepted"><day>4</day>
<month>9</month>
<year>2016</year>
</date>
</history>
<permissions><copyright-statement>© The Author(s) 2016</copyright-statement>
<license license-type="OpenAccess"><license-p><bold>Open Access</bold>
This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">http://creativecommons.org/licenses/by/4.0/</ext-link>
), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.</license-p>
</license>
</permissions>
<abstract id="Abs1"><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>
</abstract>
<kwd-group xml:lang="en"><title>Keywords</title>
<kwd>Nucleotides</kwd>
<kwd>Amide bond formation</kwd>
<kwd>NMR spectroscopy</kwd>
<kwd>Phosphonates</kwd>
</kwd-group>
<funding-group><award-group><funding-source><institution-wrap><institution-id institution-id-type="FundRef">http://dx.doi.org/10.13039/501100004281</institution-id>
<institution>Narodowe Centrum Nauki</institution>
</institution-wrap>
</funding-source>
<award-id>UMO-2013/09/B/NZ7/00729</award-id>
<principal-award-recipient><name><surname>Wróblewski</surname>
<given-names>Andrzej E.</given-names>
</name>
</principal-award-recipient>
</award-group>
</funding-group>
<funding-group><award-group><funding-source><institution-wrap><institution-id institution-id-type="FundRef">http://dx.doi.org/10.13039/501100004040</institution-id>
<institution>KU Leuven</institution>
</institution-wrap>
</funding-source>
<award-id>GOA 15/19 TBA</award-id>
<principal-award-recipient><name><surname>Schols</surname>
<given-names>Dominique</given-names>
</name>
</principal-award-recipient>
</award-group>
</funding-group>
<custom-meta-group><custom-meta><meta-name>issue-copyright-statement</meta-name>
<meta-value>© Springer-Verlag Wien 2016</meta-value>
</custom-meta>
</custom-meta-group>
</article-meta>
</front>
</pmc>
</record>
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