A novel type of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid
A convenient and efficient synthesis of a novel class of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid has been developed. The key step of the synthesis is the optimized oxidation of the 3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) analogues to the corresponding 2′-c...
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| Veröffentlicht in: | Tetrahedron 2012-05, Vol.68 (21), p.4003-4012 |
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| container_title | Tetrahedron |
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| creator | Kaiser, Martin Maxmilian Jansa, Petr Dračínský, Martin Janeba, Zlatko |
| description | A convenient and efficient synthesis of a novel class of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid has been developed. The key step of the synthesis is the optimized oxidation of the 3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) analogues to the corresponding 2′-carboxy-PME (CPME) derivatives using the TEMPO/NaClO2/NaClO oxidizing system. Although (S)-3-(adenin-9-yl)-2-(phosphonomethoxy)propanoic acid ((S)-CPMEA) has been designed as a compound with potential anti-HIV activity, none of the newly prepared CPME analogues exhibited any antiviral activity.
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| doi_str_mv | 10.1016/j.tet.2012.03.066 |
| format | Article |
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[Display omitted]</description><subject>Acyclic nucleoside phosphonates</subject><subject>Antiviral</subject><subject>antiviral properties</subject><subject>chemical structure</subject><subject>CPMEA</subject><subject>Derivatives</subject><subject>HPMPA</subject><subject>Microwave</subject><subject>Nucleosides</subject><subject>Oxidation</subject><subject>Phosphonates</subject><subject>PMEA</subject><subject>propionic acid</subject><subject>Synthesis</subject><subject>TEMPO</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><issn>0040-4020</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqNkcFu1DAQhiMEotvCA3BBOZZDwozt2ImQkKqKAlIlLnC2HHvMepXEwc6u2Lcn1bYVXIDDyIf55tOM_6J4hVAjoHy7qxdaagbIauA1SPmk2KCQomoEyqfFBkBAJYDBWXGe8w4AEBl_XpxxxlolGNsU-qqc4oGGcjnOVEZfGnu0Q7DltLcDxRwclfM25rUms1AuHaVwIFf6FMeSVZcPzTjSso0_j2_mFGczxVVhbHAvimfeDJle3r8XxbebD1-vP1W3Xz5-vr66rWyDaqkcBw_G-17JtgFOTHnettYiGA6SCXRd47yV1pNqyRojPfSCYa-c7Dn0_KJ4f_LO-34kZ2lakhn0nMJo0lFHE_SfnSls9fd40AoRW1Sr4PJekOKPPeVFjyFbGgYzUdxnzXgH2IimxX-iqISQLTKh_gOFRnDWdd2K4gm1KeacyD8uj6Dv4tY7vcat7-LWwPUa9zrz-verHyce8l2BdyeA1r8_BEo620CTJRcS2UW7GP6i_wVUdbzh</recordid><startdate>20120527</startdate><enddate>20120527</enddate><creator>Kaiser, Martin Maxmilian</creator><creator>Jansa, Petr</creator><creator>Dračínský, Martin</creator><creator>Janeba, Zlatko</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20120527</creationdate><title>A novel type of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid</title><author>Kaiser, Martin Maxmilian ; Jansa, Petr ; Dračínský, Martin ; Janeba, Zlatko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c517t-d30f0affb768503e27f388cc10a306241d95dfc6cfe78ecaa6f0b421b7d6b30b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Acyclic nucleoside phosphonates</topic><topic>Antiviral</topic><topic>antiviral properties</topic><topic>chemical structure</topic><topic>CPMEA</topic><topic>Derivatives</topic><topic>HPMPA</topic><topic>Microwave</topic><topic>Nucleosides</topic><topic>Oxidation</topic><topic>Phosphonates</topic><topic>PMEA</topic><topic>propionic acid</topic><topic>Synthesis</topic><topic>TEMPO</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kaiser, Martin Maxmilian</creatorcontrib><creatorcontrib>Jansa, Petr</creatorcontrib><creatorcontrib>Dračínský, Martin</creatorcontrib><creatorcontrib>Janeba, Zlatko</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kaiser, Martin Maxmilian</au><au>Jansa, Petr</au><au>Dračínský, Martin</au><au>Janeba, Zlatko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A novel type of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid</atitle><jtitle>Tetrahedron</jtitle><addtitle>Tetrahedron</addtitle><date>2012-05-27</date><risdate>2012</risdate><volume>68</volume><issue>21</issue><spage>4003</spage><epage>4012</epage><pages>4003-4012</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><eissn>0040-4020</eissn><abstract>A convenient and efficient synthesis of a novel class of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid has been developed. The key step of the synthesis is the optimized oxidation of the 3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) analogues to the corresponding 2′-carboxy-PME (CPME) derivatives using the TEMPO/NaClO2/NaClO oxidizing system. Although (S)-3-(adenin-9-yl)-2-(phosphonomethoxy)propanoic acid ((S)-CPMEA) has been designed as a compound with potential anti-HIV activity, none of the newly prepared CPME analogues exhibited any antiviral activity.
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| ispartof | Tetrahedron, 2012-05, Vol.68 (21), p.4003-4012 |
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| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7111817 |
| source | Elsevier ScienceDirect Journals |
| subjects | Acyclic nucleoside phosphonates Antiviral antiviral properties chemical structure CPMEA Derivatives HPMPA Microwave Nucleosides Oxidation Phosphonates PMEA propionic acid Synthesis TEMPO Tetrahedrons |
| title | A novel type of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid |
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