Stereoselective Synthesis of trans‐threo‐trans‐Oligopyrrolidines: Potential Agents for RNA Cleavage
Identifieur interne : 003120 ( Main/Exploration ); précédent : 003119; suivant : 003121Stereoselective Synthesis of trans‐threo‐trans‐Oligopyrrolidines: Potential Agents for RNA Cleavage
Auteurs : Hans-Dieter Arndt [Allemagne] ; Rüdiger Welz [Allemagne] ; Sabine Müller [Allemagne] ; Burkhart Ziemer [Allemagne] ; Ulrich Koert [Allemagne]Source :
- Chemistry – A European Journal [ 0947-6539 ] ; 2004-08-20.
Abstract
The 2,5‐trans‐substituted oligopyrrolidines constitute a promising class of novel RNA‐binding agents as well as potential building blocks for artificial anion channels. A convergent synthesis of terpyrrolidine 1 and pyrrolidino‐THF‐pyrrolidine 2 is reported, relying upon convergent coupling of 2,5‐trans‐pyrrolidinecarboxaldehydes through bridging alkyne units under Felkin–Anh control and subsequent closure of the central ring. After complete deprotection, the free polyamine products were isolated in excellent yield and purity. Crystal structure analyses of a terpyrrolidine and a pyrrolidino‐THF‐pyrrolidine documented their helical privileged conformations. The compounds were then screened for RNA cleavage activity. Unlike the only weakly active simple polyamines, p‐nitrosulfonamide 33 was found to induce cleavage at mM concentrations under physiologically relevant conditions.
A promising class of novel RNA‐binding agents has been developed by using bis‐ and terpyrrolidines with 2,5′‐threo‐trans configurations. The compounds such as depicted were synthesized stereoselectively and tested for RNA cleavage.
Url:
DOI: 10.1002/chem.200400181
Affiliations:
Links toward previous steps (curation, corpus...)
- to stream Istex, to step Corpus: 002248
- to stream Istex, to step Curation: 002248
- to stream Istex, to step Checkpoint: 000B78
- to stream Main, to step Merge: 003152
- to stream Main, to step Curation: 003120
Le document en format XML
<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title xml:lang="en">Stereoselective Synthesis of trans‐threo‐trans‐Oligopyrrolidines: Potential Agents for RNA Cleavage</title><author><name sortKey="Arndt, Hans Ieter" sort="Arndt, Hans Ieter" uniqKey="Arndt H" first="Hans-Dieter" last="Arndt">Hans-Dieter Arndt</name></author><author><name sortKey="Welz, Rudiger" sort="Welz, Rudiger" uniqKey="Welz R" first="Rüdiger" last="Welz">Rüdiger Welz</name></author><author><name sortKey="Muller, Sabine" sort="Muller, Sabine" uniqKey="Muller S" first="Sabine" last="Müller">Sabine Müller</name></author><author><name sortKey="Ziemer, Burkhart" sort="Ziemer, Burkhart" uniqKey="Ziemer B" first="Burkhart" last="Ziemer">Burkhart Ziemer</name></author><author><name sortKey="Koert, Ulrich" sort="Koert, Ulrich" uniqKey="Koert U" first="Ulrich" last="Koert">Ulrich Koert</name></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:6D4386B68FCD3EA7A029DDCFF647D72FD02A73FF</idno><date when="2004" year="2004">2004</date><idno type="doi">10.1002/chem.200400181</idno><idno type="url">https://api.istex.fr/ark:/67375/WNG-MGP6WWS0-9/fulltext.pdf</idno><idno type="wicri:Area/Istex/Corpus">002248</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">002248</idno><idno type="wicri:Area/Istex/Curation">002248</idno><idno type="wicri:Area/Istex/Checkpoint">000B78</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Checkpoint">000B78</idno><idno type="wicri:doubleKey">0947-6539:2004:Arndt H:stereoselective:synthesis:of</idno><idno type="wicri:Area/Main/Merge">003152</idno><idno type="wicri:Area/Main/Curation">003120</idno><idno type="wicri:Area/Main/Exploration">003120</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main">Stereoselective Synthesis of trans‐threo‐trans‐Oligopyrrolidines: Potential Agents for RNA Cleavage</title><author><name sortKey="Arndt, Hans Ieter" sort="Arndt, Hans Ieter" uniqKey="Arndt H" first="Hans-Dieter" last="Arndt">Hans-Dieter Arndt</name><affiliation wicri:level="3"><country xml:lang="fr">Allemagne</country><wicri:regionArea>Institut für Chemie der Humboldt‐Universität zu Berlin, Brook‐Taylor‐Strasse 2, 12489 Berlin</wicri:regionArea><placeName><region type="land" nuts="3">Berlin</region><settlement type="city">Berlin</settlement></placeName></affiliation><affiliation wicri:level="3"><country xml:lang="fr">Allemagne</country><wicri:regionArea>New Address: Max‐Planck Institut fur Molekulare Physiologie, Abteilung IV—Chemische Biologie, Otto‐Hahn‐Strasse 11, 44227 Dortmund</wicri:regionArea><placeName><region type="land" nuts="1">Rhénanie-du-Nord-Westphalie</region><region type="district" nuts="2">District d'Arnsberg</region><settlement type="city">Dortmund</settlement></placeName></affiliation></author><author><name sortKey="Welz, Rudiger" sort="Welz, Rudiger" uniqKey="Welz R" first="Rüdiger" last="Welz">Rüdiger Welz</name><affiliation wicri:level="3"><country xml:lang="fr">Allemagne</country><wicri:regionArea>Institut für Chemie der Humboldt‐Universität zu Berlin, Brook‐Taylor‐Strasse 2, 12489 Berlin</wicri:regionArea><placeName><region type="land" nuts="3">Berlin</region><settlement type="city">Berlin</settlement></placeName></affiliation></author><author><name sortKey="Muller, Sabine" sort="Muller, Sabine" uniqKey="Muller S" first="Sabine" last="Müller">Sabine Müller</name><affiliation wicri:level="3"><country xml:lang="fr">Allemagne</country><wicri:regionArea>Institut für Chemie der Humboldt‐Universität zu Berlin, Brook‐Taylor‐Strasse 2, 12489 Berlin</wicri:regionArea><placeName><region type="land" nuts="3">Berlin</region><settlement type="city">Berlin</settlement></placeName></affiliation><affiliation wicri:level="1"><country xml:lang="fr">Allemagne</country><wicri:regionArea>New Address: Fakultät für Chemie, NC 3/171, Universitätsstrasse 150, 44780 Bochum</wicri:regionArea><wicri:noRegion>44780 Bochum</wicri:noRegion><wicri:noRegion>44780 Bochum</wicri:noRegion></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Allemagne</country></affiliation></author><author><name sortKey="Ziemer, Burkhart" sort="Ziemer, Burkhart" uniqKey="Ziemer B" first="Burkhart" last="Ziemer">Burkhart Ziemer</name><affiliation wicri:level="3"><country xml:lang="fr">Allemagne</country><wicri:regionArea>Institut für Chemie der Humboldt‐Universität zu Berlin, Brook‐Taylor‐Strasse 2, 12489 Berlin</wicri:regionArea><placeName><region type="land" nuts="3">Berlin</region><settlement type="city">Berlin</settlement></placeName></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Allemagne</country></affiliation></author><author><name sortKey="Koert, Ulrich" sort="Koert, Ulrich" uniqKey="Koert U" first="Ulrich" last="Koert">Ulrich Koert</name><affiliation></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Allemagne</country></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Chemistry – A European Journal</title><idno type="ISSN">0947-6539</idno><idno type="eISSN">1521-3765</idno><imprint><biblScope unit="vol">10</biblScope><biblScope unit="issue">16</biblScope><biblScope unit="page" from="3945">3945</biblScope><biblScope unit="page" to="3962">3962</biblScope><biblScope unit="page-count">18</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2004-08-20">2004-08-20</date></imprint><idno type="ISSN">0947-6539</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0947-6539</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The 2,5‐trans‐substituted oligopyrrolidines constitute a promising class of novel RNA‐binding agents as well as potential building blocks for artificial anion channels. A convergent synthesis of terpyrrolidine 1 and pyrrolidino‐THF‐pyrrolidine 2 is reported, relying upon convergent coupling of 2,5‐trans‐pyrrolidinecarboxaldehydes through bridging alkyne units under Felkin–Anh control and subsequent closure of the central ring. After complete deprotection, the free polyamine products were isolated in excellent yield and purity. Crystal structure analyses of a terpyrrolidine and a pyrrolidino‐THF‐pyrrolidine documented their helical privileged conformations. The compounds were then screened for RNA cleavage activity. Unlike the only weakly active simple polyamines, p‐nitrosulfonamide 33 was found to induce cleavage at mM concentrations under physiologically relevant conditions.</div><div type="abstract" xml:lang="en">A promising class of novel RNA‐binding agents has been developed by using bis‐ and terpyrrolidines with 2,5′‐threo‐trans configurations. The compounds such as depicted were synthesized stereoselectively and tested for RNA cleavage.</div></front></TEI><affiliations><list><country><li>Allemagne</li></country><region><li>Berlin</li><li>District d'Arnsberg</li><li>Rhénanie-du-Nord-Westphalie</li></region><settlement><li>Berlin</li><li>Dortmund</li></settlement></list><tree><country name="Allemagne"><region name="Berlin"><name sortKey="Arndt, Hans Ieter" sort="Arndt, Hans Ieter" uniqKey="Arndt H" first="Hans-Dieter" last="Arndt">Hans-Dieter Arndt</name></region><name sortKey="Arndt, Hans Ieter" sort="Arndt, Hans Ieter" uniqKey="Arndt H" first="Hans-Dieter" last="Arndt">Hans-Dieter Arndt</name><name sortKey="Koert, Ulrich" sort="Koert, Ulrich" uniqKey="Koert U" first="Ulrich" last="Koert">Ulrich Koert</name><name sortKey="Muller, Sabine" sort="Muller, Sabine" uniqKey="Muller S" first="Sabine" last="Müller">Sabine Müller</name><name sortKey="Muller, Sabine" sort="Muller, Sabine" uniqKey="Muller S" first="Sabine" last="Müller">Sabine Müller</name><name sortKey="Muller, Sabine" sort="Muller, Sabine" uniqKey="Muller S" first="Sabine" last="Müller">Sabine Müller</name><name sortKey="Welz, Rudiger" sort="Welz, Rudiger" uniqKey="Welz R" first="Rüdiger" last="Welz">Rüdiger Welz</name><name sortKey="Ziemer, Burkhart" sort="Ziemer, Burkhart" uniqKey="Ziemer B" first="Burkhart" last="Ziemer">Burkhart Ziemer</name><name sortKey="Ziemer, Burkhart" sort="Ziemer, Burkhart" uniqKey="Ziemer B" first="Burkhart" last="Ziemer">Burkhart Ziemer</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Sante/explor/MersV1/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 003120 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 003120 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Sante
|area= MersV1
|flux= Main
|étape= Exploration
|type= RBID
|clé= ISTEX:6D4386B68FCD3EA7A029DDCFF647D72FD02A73FF
|texte= Stereoselective Synthesis of trans‐threo‐trans‐Oligopyrrolidines: Potential Agents for RNA Cleavage
}}
| This area was generated with Dilib version V0.6.33. |  |