Synthesis of novel N-acyl-β-d-glucopyranosylamines and ureas as potential lead cytostatic agents
Identifieur interne : 000F42 ( Main/Exploration ); précédent : 000F41; suivant : 000F43Synthesis of novel N-acyl-β-d-glucopyranosylamines and ureas as potential lead cytostatic agents
Auteurs : Vanessa Parmenopoulou [Grèce] ; Stella Manta [Grèce] ; Athina Dimopoulou [Grèce] ; Nikolaos Kollatos [Grèce] ; Dominique Schols [Belgique] ; Dimitri Komiotis [Grèce]Source :
- Medicinal Chemistry Research [ 1054-2523 ] ; 2016.
Abstract
Novel classes of acetylated and fully deprotected
Url:
DOI: 10.1007/s00044-016-1539-5
PubMed: NONE
PubMed Central: 7079967
Affiliations:
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Larissa</wicri:regionArea><wicri:noRegion>41 221 Larissa</wicri:noRegion></affiliation></author><author><name sortKey="Manta, Stella" sort="Manta, Stella" uniqKey="Manta S" first="Stella" last="Manta">Stella Manta</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.410558.d</institution-id><institution-id institution-id-type="ISNI">0000000100356670</institution-id><institution>Laboratory of Bioorganic Chemistry, Department of Biochemistry and Biotechnology,</institution><institution>University of Thessaly,</institution></institution-wrap>26 Ploutonos Str., 41 221 Larissa, Greece</nlm:aff><country xml:lang="fr">Grèce</country><wicri:regionArea>26 Ploutonos Str., 41 221 Larissa</wicri:regionArea><wicri:noRegion>41 221 Larissa</wicri:noRegion></affiliation></author><author><name sortKey="Dimopoulou, Athina" sort="Dimopoulou, Athina" uniqKey="Dimopoulou A" first="Athina" last="Dimopoulou">Athina Dimopoulou</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.410558.d</institution-id><institution-id institution-id-type="ISNI">0000000100356670</institution-id><institution>Laboratory of Bioorganic Chemistry, Department of Biochemistry and Biotechnology,</institution><institution>University of Thessaly,</institution></institution-wrap>26 Ploutonos Str., 41 221 Larissa, Greece</nlm:aff><country xml:lang="fr">Grèce</country><wicri:regionArea>26 Ploutonos Str., 41 221 Larissa</wicri:regionArea><wicri:noRegion>41 221 Larissa</wicri:noRegion></affiliation></author><author><name sortKey="Kollatos, Nikolaos" sort="Kollatos, Nikolaos" uniqKey="Kollatos N" first="Nikolaos" last="Kollatos">Nikolaos Kollatos</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.410558.d</institution-id><institution-id 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Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Louvain</wicri:regionArea></affiliation></author><author><name sortKey="Komiotis, Dimitri" sort="Komiotis, Dimitri" uniqKey="Komiotis D" first="Dimitri" last="Komiotis">Dimitri Komiotis</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.410558.d</institution-id><institution-id institution-id-type="ISNI">0000000100356670</institution-id><institution>Laboratory of Bioorganic Chemistry, Department of Biochemistry and Biotechnology,</institution><institution>University of Thessaly,</institution></institution-wrap>26 Ploutonos Str., 41 221 Larissa, Greece</nlm:aff><country xml:lang="fr">Grèce</country><wicri:regionArea>26 Ploutonos Str., 41 221 Larissa</wicri:regionArea><wicri:noRegion>41 221 Larissa</wicri:noRegion></affiliation></author></analytic><series><title level="j">Medicinal Chemistry Research</title><idno type="ISSN">1054-2523</idno><idno type="eISSN">1554-8120</idno><imprint><date when="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p id="Par1">Novel classes of acetylated and fully deprotected <italic>N</italic>-acyl-<italic>β</italic>-<sc>d</sc>-glucopyranosylamines and ureas have been synthesized and biologically evaluated. Acylation of the per-<italic>O</italic>-acetylated <italic>β</italic>-<sc>d</sc>-glucopyranosylurea (<bold>5</bold>), easily prepared via its corresponding phosphinimine derivative, by zinc chloride catalyzed reaction of the corresponding acyl chlorides RCOCl (<bold>a</bold>–<bold>f</bold>) gave the protected <italic>N</italic>-acyl-<italic>β</italic>-<sc>d</sc>-glucopyranosylureas (<bold>6a</bold>–<bold>f</bold>), in acceptable-to-moderate yields. Subsequent deacetylation of analogues <bold>6a</bold>–<bold>f</bold> under Zemplén conditions afforded the fully deprotected derivatives <bold>7a,b,d,e,f</bold>, while the desired urea <bold>7c</bold> was formed after treatment of <bold>6c</bold> with dibutyltin oxide. All protected and unprotected compounds were examined for their cytotoxic activity in different L1210, CEM and HeLa tumor cell lines and were also evaluated against a broad panel of DΝΑ and RNA viruses. Derivative <bold>7c</bold> exhibited cytostatic activity against the three evaluated tumor cell lines (IC<sub>50</sub> 9–24 μΜ) and might be the basis for the synthesis of structure-related derivatives with improved cytostatic potential. Only analogue <bold>6f</bold> weakly but significantly inhibited the replication of parainfluenza-3 virus, Sindbis virus and Coxsackie virus B4 in cell cultures at concentrations of 45–58 μM.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Agoston, K" uniqKey="Agoston K">K Agoston</name></author><author><name sortKey="Dob, A" uniqKey="Dob A">A Dobó</name></author><author><name sortKey="Rak, J" uniqKey="Rak J">J Rákó</name></author><author><name sortKey="Kerekgyart, J" uniqKey="Kerekgyart J">J Kerékgyártó</name></author><author><name sortKey="Szurmai, Z" uniqKey="Szurmai Z">Z Szurmai</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Blanc, J" uniqKey="Blanc J">J Blanc</name></author><author><name sortKey="Geney, R" uniqKey="Geney R">R Geney</name></author><author><name sortKey="Menet, C" uniqKey="Menet C">C Menet</name></author></analytic></biblStruct><biblStruct><analytic><author><name 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Kiritsis</name></author><author><name sortKey="Gkaragkouni, Dn" uniqKey="Gkaragkouni D">DN Gkaragkouni</name></author><author><name sortKey="Papasotiriou, I" uniqKey="Papasotiriou I">I Papasotiriou</name></author><author><name sortKey="Balzarini, J" uniqKey="Balzarini J">J Balzarini</name></author><author><name sortKey="Komiotis, D" uniqKey="Komiotis D">D Komiotis</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Ferlay, J" uniqKey="Ferlay J">J Ferlay</name></author><author><name sortKey="Soerjomataram, I" uniqKey="Soerjomataram I">I Soerjomataram</name></author><author><name sortKey="Dikshit, R" uniqKey="Dikshit R">R Dikshit</name></author><author><name sortKey="Eser, S" uniqKey="Eser S">S Eser</name></author><author><name sortKey="Mathers, C" uniqKey="Mathers C">C Mathers</name></author><author><name sortKey="Rebelo, M" uniqKey="Rebelo M">M Rebelo</name></author><author><name sortKey="Parkin, Dm" uniqKey="Parkin D">DM 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Mi" uniqKey="Churchwell M">MI Churchwell</name></author><author><name sortKey="Cho, Mh" uniqKey="Cho M">MH Cho</name></author><author><name sortKey="Doerge, Dr" uniqKey="Doerge D">DR Doerge</name></author><author><name sortKey="Helferich, Wg" uniqKey="Helferich W">WG Helferich</name></author><author><name sortKey="Hergenrother, Pj" uniqKey="Hergenrother P">PJ Hergenrother</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Sausville, Ea" uniqKey="Sausville E">EA Sausville</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Sethi, N" uniqKey="Sethi N">N Sethi</name></author><author><name sortKey="Kang, Y" uniqKey="Kang Y">Y Kang</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Somsak, L" uniqKey="Somsak L">L Somsák</name></author><author><name sortKey="Felfoldi, N" uniqKey="Felfoldi N">N Felföldi</name></author><author><name sortKey="K Nya, B" uniqKey="K Nya B">B Kónya</name></author><author><name sortKey="Huse, C" uniqKey="Huse C">C Hüse</name></author><author><name sortKey="Telep, K" uniqKey="Telep K">K Telepó</name></author><author><name sortKey="Bokor, E" uniqKey="Bokor E">E Bokor</name></author><author><name sortKey="Czifrak, K" uniqKey="Czifrak K">K Czifrák</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Somsak, L" uniqKey="Somsak L">L Somsák</name></author><author><name sortKey="Czifrak, K" uniqKey="Czifrak K">K Czifrák</name></author><author><name sortKey="T Th, M" uniqKey="T Th M">M Tóth</name></author><author><name sortKey="Bokor, E" uniqKey="Bokor E">E Bokor</name></author><author><name sortKey="Chrysina, Ed" uniqKey="Chrysina E">ED Chrysina</name></author><author><name sortKey="Alexacou, Km" uniqKey="Alexacou K">KM Alexacou</name></author><author><name sortKey="Hayes, Jm" uniqKey="Hayes J">JM Hayes</name></author><author><name sortKey="Tiraidis, C" uniqKey="Tiraidis C">C 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Lynch</name></author><author><name sortKey="Lowinger, T" uniqKey="Lowinger T">T Lowinger</name></author><author><name sortKey="Dumas, J" uniqKey="Dumas J">J Dumas</name></author><author><name sortKey="Smith, Ra" uniqKey="Smith R">RA Smith</name></author><author><name sortKey="Schwartz, B" uniqKey="Schwartz B">B Schwartz</name></author><author><name sortKey="Simantov, R" uniqKey="Simantov R">R Simantov</name></author><author><name sortKey="Kelley, S" uniqKey="Kelley S">S Kelley</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Zhang, B" uniqKey="Zhang B">B Zhang</name></author><author><name sortKey="Zhao, Y" uniqKey="Zhao Y">Y Zhao</name></author><author><name sortKey="Zhai, X" uniqKey="Zhai X">X Zhai</name></author><author><name sortKey="Wang, L" uniqKey="Wang L">L Wang</name></author><author><name sortKey="Yang, J" uniqKey="Yang J">J Yang</name></author><author><name sortKey="Tan, Z" uniqKey="Tan Z">Z Tan</name></author><author><name sortKey="Gong, P" uniqKey="Gong P">P Gong</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Belgique</li><li>Grèce</li></country></list><tree><country name="Grèce"><noRegion><name sortKey="Parmenopoulou, Vanessa" sort="Parmenopoulou, Vanessa" uniqKey="Parmenopoulou V" first="Vanessa" last="Parmenopoulou">Vanessa Parmenopoulou</name></noRegion><name sortKey="Dimopoulou, Athina" sort="Dimopoulou, Athina" uniqKey="Dimopoulou A" first="Athina" last="Dimopoulou">Athina Dimopoulou</name><name sortKey="Kollatos, Nikolaos" sort="Kollatos, Nikolaos" uniqKey="Kollatos N" first="Nikolaos" last="Kollatos">Nikolaos Kollatos</name><name sortKey="Komiotis, Dimitri" sort="Komiotis, Dimitri" uniqKey="Komiotis D" first="Dimitri" last="Komiotis">Dimitri Komiotis</name><name sortKey="Manta, Stella" sort="Manta, Stella" uniqKey="Manta S" first="Stella" last="Manta">Stella Manta</name></country><country name="Belgique"><noRegion><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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