CovidV2, Main, Exploration, bibRecord, 001372

Synthesis of 4′-Ethynyl-2′-deoxy-4′-thioribonucleosides and Discovery of a Highly Potent and Less Toxic NRTI

Identifieur interne : 001372 ( Main/Exploration ); précédent : 001371; suivant : 001373

Synthesis of 4′-Ethynyl-2′-deoxy-4′-thioribonucleosides and Discovery of a Highly Potent and Less Toxic NRTI

Auteurs : Kazuhiro Haraguchi [Japon] ; Hisashi Shimada [Japon] ; Keigo Kimura [Japon] ; Genta Akutsu [Japon] ; Hiromichi Tanaka [Japon] ; Hiroshi Abe [Japon] ; Takayuki Hamasaki [Japon] ; Masanori Baba [Japon] ; Elizabeth A. Gullen [États-Unis] ; Ginger E. Dutschman [États-Unis] ; Yung-Chi Cheng [États-Unis] ; Jan Balzarini [Belgique]

Source :

ACS Medicinal Chemistry Letters [ 1948-5875 ] ; 2011.

RBID : PMC:3686520

Abstract

The synthesis of 4′-ethynyl-2′-deoxy-4′-thioribonucleosides was carried out utilizing an electrophilic glycosidation in which 4-ethynyl-4-thiofuranoid glycal 16 served as a glycosyl donor. Electrophilic glycosidation between 16 and the silylated nucleobases (N⁴-acetylcytosine, N⁶-benzoyladenine, and N²-acetyl-O⁶-diphenylcarbamoylguanine) was carried out in the presence of N-iodosuccinimide (NIS), leading to the exclusive formation of the desired β-anomers 29, 33, and 36. Anti-HIV studies demonstrated that these 4′-thio nucleosides were less cytotoxic to T-lymphocyte (i.e., MT-4 cells) than the corresponding 4′-ethynyl derivatives of 2′-deoxycytidine (44), 2′-deoxyadenosine (45), and 2′-deoxyguanosine (46). Comparison of the selectivity indices (SI) was made between 4′-thionucleosides (32, 41, and 43) and the corresponding 4′-oxygen analogues 44-46 by using the reported CC₅₀ and EC₅₀ values. In the case of cytosine and adenine nucleosides, comparable SI values were obtained as follows: 32 (545) and 44 (458); 41 (>230) and 45 (1630). In contrast, 4′-ethynyl-2′-deoxy-4′-thioguanosine 43 was found to possess a SI value of >18200, which is 20 times better than that of 46 (933).

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3686520

DOI: 10.1021/ml2001054
PubMed: 23795238
PubMed Central: 3686520

Affiliations:

Le document en format XML

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<author><name sortKey="Haraguchi, Kazuhiro" sort="Haraguchi, Kazuhiro" uniqKey="Haraguchi K" first="Kazuhiro" last="Haraguchi">Kazuhiro Haraguchi</name>
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, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan</nlm:aff>
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, New Haven, Connecticut 06520, United States</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>, New Haven, Connecticut 06520</wicri:regionArea>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Synthesis of 4′-Ethynyl-2′-deoxy-4′-thioribonucleosides and Discovery of a Highly Potent and Less Toxic NRTI</title>
<author><name sortKey="Haraguchi, Kazuhiro" sort="Haraguchi, Kazuhiro" uniqKey="Haraguchi K" first="Kazuhiro" last="Haraguchi">Kazuhiro Haraguchi</name>
<affiliation wicri:level="1"><nlm:aff id="aff1">School of Pharmacy,<institution>Showa University</institution>
, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan</nlm:aff>
<country xml:lang="fr">Japon</country>
<wicri:regionArea>, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555</wicri:regionArea>
<placeName><settlement type="city">Tokyo</settlement>
<region type="région">Région de Kantō</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Shimada, Hisashi" sort="Shimada, Hisashi" uniqKey="Shimada H" first="Hisashi" last="Shimada">Hisashi Shimada</name>
<affiliation wicri:level="1"><nlm:aff id="aff1">School of Pharmacy,<institution>Showa University</institution>
, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan</nlm:aff>
<country xml:lang="fr">Japon</country>
<wicri:regionArea>, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555</wicri:regionArea>
<placeName><settlement type="city">Tokyo</settlement>
<region type="région">Région de Kantō</region>
</placeName>
</affiliation>
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<author><name sortKey="Kimura, Keigo" sort="Kimura, Keigo" uniqKey="Kimura K" first="Keigo" last="Kimura">Keigo Kimura</name>
<affiliation wicri:level="1"><nlm:aff id="aff1">School of Pharmacy,<institution>Showa University</institution>
, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan</nlm:aff>
<country xml:lang="fr">Japon</country>
<wicri:regionArea>, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555</wicri:regionArea>
<placeName><settlement type="city">Tokyo</settlement>
<region type="région">Région de Kantō</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Akutsu, Genta" sort="Akutsu, Genta" uniqKey="Akutsu G" first="Genta" last="Akutsu">Genta Akutsu</name>
<affiliation wicri:level="1"><nlm:aff id="aff1">School of Pharmacy,<institution>Showa University</institution>
, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan</nlm:aff>
<country xml:lang="fr">Japon</country>
<wicri:regionArea>, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555</wicri:regionArea>
<placeName><settlement type="city">Tokyo</settlement>
<region type="région">Région de Kantō</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Tanaka, Hiromichi" sort="Tanaka, Hiromichi" uniqKey="Tanaka H" first="Hiromichi" last="Tanaka">Hiromichi Tanaka</name>
<affiliation wicri:level="1"><nlm:aff id="aff1">School of Pharmacy,<institution>Showa University</institution>
, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan</nlm:aff>
<country xml:lang="fr">Japon</country>
<wicri:regionArea>, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555</wicri:regionArea>
<placeName><settlement type="city">Tokyo</settlement>
<region type="région">Région de Kantō</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Abe, Hiroshi" sort="Abe, Hiroshi" uniqKey="Abe H" first="Hiroshi" last="Abe">Hiroshi Abe</name>
<affiliation wicri:level="1"><nlm:aff id="aff2">RIKEN Advanced Science Institute,<institution>Nanomedical Engineering Laboratory</institution>
, 2-1, Hirosawa, Wako-shi, Saitama 351-0198, Japan</nlm:aff>
<country xml:lang="fr">Japon</country>
<wicri:regionArea>, 2-1, Hirosawa, Wako-shi, Saitama 351-0198</wicri:regionArea>
<wicri:noRegion>Saitama 351-0198</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Hamasaki, Takayuki" sort="Hamasaki, Takayuki" uniqKey="Hamasaki T" first="Takayuki" last="Hamasaki">Takayuki Hamasaki</name>
<affiliation wicri:level="1"><nlm:aff id="aff3">Division of Antiviral Chemotherapy, Center for Chronic Viral Diseases, Graduate School of Medical and Dental Sciences,<institution>Kagoshima University</institution>
, Kagoshima 89-8544, Japan</nlm:aff>
<country xml:lang="fr">Japon</country>
<wicri:regionArea>, Kagoshima 89-8544</wicri:regionArea>
<wicri:noRegion>Kagoshima 89-8544</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Baba, Masanori" sort="Baba, Masanori" uniqKey="Baba M" first="Masanori" last="Baba">Masanori Baba</name>
<affiliation wicri:level="1"><nlm:aff id="aff3">Division of Antiviral Chemotherapy, Center for Chronic Viral Diseases, Graduate School of Medical and Dental Sciences,<institution>Kagoshima University</institution>
, Kagoshima 89-8544, Japan</nlm:aff>
<country xml:lang="fr">Japon</country>
<wicri:regionArea>, Kagoshima 89-8544</wicri:regionArea>
<wicri:noRegion>Kagoshima 89-8544</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Gullen, Elizabeth A" sort="Gullen, Elizabeth A" uniqKey="Gullen E" first="Elizabeth A." last="Gullen">Elizabeth A. Gullen</name>
<affiliation wicri:level="1"><nlm:aff id="aff4">Department of Pharmacology, School of Medicine,<institution>Yale University</institution>
, New Haven, Connecticut 06520, United States</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>, New Haven, Connecticut 06520</wicri:regionArea>
<wicri:noRegion>Connecticut 06520</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Dutschman, Ginger E" sort="Dutschman, Ginger E" uniqKey="Dutschman G" first="Ginger E." last="Dutschman">Ginger E. Dutschman</name>
<affiliation wicri:level="1"><nlm:aff id="aff4">Department of Pharmacology, School of Medicine,<institution>Yale University</institution>
, New Haven, Connecticut 06520, United States</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>, New Haven, Connecticut 06520</wicri:regionArea>
<wicri:noRegion>Connecticut 06520</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Cheng, Yung Chi" sort="Cheng, Yung Chi" uniqKey="Cheng Y" first="Yung-Chi" last="Cheng">Yung-Chi Cheng</name>
<affiliation wicri:level="1"><nlm:aff id="aff4">Department of Pharmacology, School of Medicine,<institution>Yale University</institution>
, New Haven, Connecticut 06520, United States</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>, New Haven, Connecticut 06520</wicri:regionArea>
<wicri:noRegion>Connecticut 06520</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name>
<affiliation wicri:level="1"><nlm:aff id="aff5">Rega Institute for Medical Research,<institution>Katholieke Universiteit Leuven</institution>
, B-3000 Leuven, Belgium</nlm:aff>
<country xml:lang="fr">Belgique</country>
<wicri:regionArea>, B-3000 Leuven</wicri:regionArea>
<wicri:noRegion>B-3000 Leuven</wicri:noRegion>
</affiliation>
</author>
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<series><title level="j">ACS Medicinal Chemistry Letters</title>
<idno type="ISSN">1948-5875</idno>
<idno type="eISSN">1948-5875</idno>
<imprint><date when="2011">2011</date>
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<front><div type="abstract" xml:lang="en"><p content-type="toc-graphic"><graphic xlink:href="ml-2011-001054_0014" id="ab-tgr1"></graphic>
</p>
<p>The synthesis of 4′-ethynyl-2′-deoxy-4′-thioribonucleosides was carried out utilizing an electrophilic glycosidation in which 4-ethynyl-4-thiofuranoid glycal <bold>16</bold>
 served as a glycosyl donor. Electrophilic glycosidation between <bold>16</bold>
 and the silylated nucleobases (<italic>N</italic>
<sup>4</sup>
-acetylcytosine, <italic>N</italic>
<sup>6</sup>
-benzoyladenine, and <italic>N</italic>
<sup>2</sup>
-acetyl-<italic>O</italic>
<sup>6</sup>
-diphenylcarbamoylguanine) was carried out in the presence of <italic>N</italic>
-iodosuccinimide (NIS), leading to the exclusive formation of the desired β-anomers <bold>29</bold>
, <bold>33</bold>
, and <bold>36</bold>
. Anti-HIV studies demonstrated that these 4′-thio nucleosides were less cytotoxic to T-lymphocyte (i.e., MT-4 cells) than the corresponding 4′-ethynyl derivatives of 2′-deoxycytidine (<bold>44</bold>
), 2′-deoxyadenosine (<bold>45</bold>
), and 2′-deoxyguanosine (<bold>46</bold>
). Comparison of the selectivity indices (SI) was made between 4′-thionucleosides (<bold>32</bold>
, <bold>41</bold>
, and <bold>43</bold>
) and the corresponding 4′-oxygen analogues <bold>44</bold>
-<bold>46</bold>
 by using the reported CC<sub>50</sub>
 and EC<sub>50</sub>
 values. In the case of cytosine and adenine nucleosides, comparable SI values were obtained as follows: <bold>32</bold>
 (545) and <bold>44</bold>
 (458); <bold>41</bold>
 (>230) and <bold>45</bold>
 (1630). In contrast, 4′-ethynyl-2′-deoxy-4′-thioguanosine <bold>43</bold>
 was found to possess a SI value of >18200, which is 20 times better than that of <bold>46</bold>
 (933).</p>
</div>
</front>
</TEI>
<affiliations><list><country><li>Belgique</li>
<li>Japon</li>
<li>États-Unis</li>
</country>
<region><li>Région de Kantō</li>
</region>
<settlement><li>Tokyo</li>
</settlement>
</list>
<tree><country name="Japon"><region name="Région de Kantō"><name sortKey="Haraguchi, Kazuhiro" sort="Haraguchi, Kazuhiro" uniqKey="Haraguchi K" first="Kazuhiro" last="Haraguchi">Kazuhiro Haraguchi</name>
</region>
<name sortKey="Abe, Hiroshi" sort="Abe, Hiroshi" uniqKey="Abe H" first="Hiroshi" last="Abe">Hiroshi Abe</name>
<name sortKey="Akutsu, Genta" sort="Akutsu, Genta" uniqKey="Akutsu G" first="Genta" last="Akutsu">Genta Akutsu</name>
<name sortKey="Baba, Masanori" sort="Baba, Masanori" uniqKey="Baba M" first="Masanori" last="Baba">Masanori Baba</name>
<name sortKey="Hamasaki, Takayuki" sort="Hamasaki, Takayuki" uniqKey="Hamasaki T" first="Takayuki" last="Hamasaki">Takayuki Hamasaki</name>
<name sortKey="Kimura, Keigo" sort="Kimura, Keigo" uniqKey="Kimura K" first="Keigo" last="Kimura">Keigo Kimura</name>
<name sortKey="Shimada, Hisashi" sort="Shimada, Hisashi" uniqKey="Shimada H" first="Hisashi" last="Shimada">Hisashi Shimada</name>
<name sortKey="Tanaka, Hiromichi" sort="Tanaka, Hiromichi" uniqKey="Tanaka H" first="Hiromichi" last="Tanaka">Hiromichi Tanaka</name>
</country>
<country name="États-Unis"><noRegion><name sortKey="Gullen, Elizabeth A" sort="Gullen, Elizabeth A" uniqKey="Gullen E" first="Elizabeth A." last="Gullen">Elizabeth A. Gullen</name>
</noRegion>
<name sortKey="Cheng, Yung Chi" sort="Cheng, Yung Chi" uniqKey="Cheng Y" first="Yung-Chi" last="Cheng">Yung-Chi Cheng</name>
<name sortKey="Dutschman, Ginger E" sort="Dutschman, Ginger E" uniqKey="Dutschman G" first="Ginger E." last="Dutschman">Ginger E. Dutschman</name>
</country>
<country name="Belgique"><noRegion><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name>
</noRegion>
</country>
</tree>
</affiliations>
</record>

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   |texte=   Synthesis of 4′-Ethynyl-2′-deoxy-4′-thioribonucleosides and Discovery of a Highly Potent and Less Toxic NRTI
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Synthesis of 4′-Ethynyl-2′-deoxy-4′-thioribonucleosides and Discovery of a Highly Potent and Less Toxic NRTI

Synthesis of 4′-Ethynyl-2′-deoxy-4′-thioribonucleosides and Discovery of a Highly Potent and Less Toxic NRTI

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	Serveur d'exploration Covid (26 mars)
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