Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents
Synthesis of 1-beta-D-ribofuranosyltetrazole and two 5-substituted derivatives, i.e., the 5-carboxamide and 5-acetamide, is described. The stereochemical structure of the parent tetrazole ribonucleoside has been established by means of nuclear Overhauser effect and x-ray crystallography. By analogy...
Gespeichert in:
| Veröffentlicht in: | Journal of medicinal chemistry 1976-02, Vol.19 (2), p.286-290 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 290 |
|---|---|
| container_issue | 2 |
| container_start_page | 286 |
| container_title | Journal of medicinal chemistry |
| container_volume | 19 |
| creator | Poonian, Mohindar S Nowoswiat, Eugene F Blount, John F Williams, Thomas H Pitcher, Ross G Kramer, Michael J |
| description | Synthesis of 1-beta-D-ribofuranosyltetrazole and two 5-substituted derivatives, i.e., the 5-carboxamide and 5-acetamide, is described. The stereochemical structure of the parent tetrazole ribonucleoside has been established by means of nuclear Overhauser effect and x-ray crystallography. By analogy to the parent compound, the two 5-substituted tetrazole nucleosides are also assigned the beta configuration on the basis of the NMR coupling constant of the anomeric proton and the site of N-ribosylation is determined by 13C NMR studies. Results are also presented on antiviral testing of these synthetic tetrazole nucleosides against influenza A2/Asian/J-305 virus infection in mice. |
| doi_str_mv | 10.1021/jm00224a016 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_83356189</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>83356189</sourcerecordid><originalsourceid>FETCH-LOGICAL-a354t-670a3b8b3800e0b1a5d10c2bc5839ef9b7ad71d3c789a18eeb03f12a5dbe711f3</originalsourceid><addsrcrecordid>eNptkEtL7TAUhYNc0eNj5PhCR9eBVHeSPtKhyPUBiuJj4iTstLveHHsab5KK-uvtoaIOHG1Y62Nt-Bjb4bDPQfCD-QJAiAyBFytsxnMBaaYg-8VmyzwVhZDrbCOEOQBILuQaW-MiqxRUM3Z589rHfxRsSFybRIoe31xHibfG9UPdkQu2oZBg3yQjZ31Cz9gNGK3rE1zm0T5bj12CD9THsMVWW-wCbX_cTXZ3_Pf26DQ9vzw5Ozo8T1HmWUyLElAaZaQCIDAc84ZDLUydK1lRW5kSm5I3si5VhVwRGZAtFyNmqOS8lZvsz7T75N3_gULUCxtq6jrsyQ1BKynzgqtqBPcmsPYuBE-tfvJ2gf5Vc9BLffqbvpH-_TE7mAU1X-zka-zTqbch0stnjf5RF6Usc317daPV_cn1BVzd64uR3514rIOeu8H3o5QfP78DcUCHXw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>83356189</pqid></control><display><type>article</type><title>Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents</title><source>MEDLINE</source><source>ACS Publications</source><creator>Poonian, Mohindar S ; Nowoswiat, Eugene F ; Blount, John F ; Williams, Thomas H ; Pitcher, Ross G ; Kramer, Michael J</creator><creatorcontrib>Poonian, Mohindar S ; Nowoswiat, Eugene F ; Blount, John F ; Williams, Thomas H ; Pitcher, Ross G ; Kramer, Michael J</creatorcontrib><description>Synthesis of 1-beta-D-ribofuranosyltetrazole and two 5-substituted derivatives, i.e., the 5-carboxamide and 5-acetamide, is described. The stereochemical structure of the parent tetrazole ribonucleoside has been established by means of nuclear Overhauser effect and x-ray crystallography. By analogy to the parent compound, the two 5-substituted tetrazole nucleosides are also assigned the beta configuration on the basis of the NMR coupling constant of the anomeric proton and the site of N-ribosylation is determined by 13C NMR studies. Results are also presented on antiviral testing of these synthetic tetrazole nucleosides against influenza A2/Asian/J-305 virus infection in mice.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00224a016</identifier><identifier>PMID: 1249809</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Antiviral Agents - chemical synthesis ; Antiviral Agents - therapeutic use ; Azoles - chemical synthesis ; Crystallography ; Magnetic Resonance Spectroscopy ; Mice ; Models, Molecular ; Molecular Conformation ; Orthomyxoviridae Infections - drug therapy ; Ribonucleosides - chemical synthesis ; Ribonucleosides - therapeutic use ; Tetrazoles - chemical synthesis ; Tetrazoles - therapeutic use</subject><ispartof>Journal of medicinal chemistry, 1976-02, Vol.19 (2), p.286-290</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a354t-670a3b8b3800e0b1a5d10c2bc5839ef9b7ad71d3c789a18eeb03f12a5dbe711f3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00224a016$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00224a016$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1249809$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Poonian, Mohindar S</creatorcontrib><creatorcontrib>Nowoswiat, Eugene F</creatorcontrib><creatorcontrib>Blount, John F</creatorcontrib><creatorcontrib>Williams, Thomas H</creatorcontrib><creatorcontrib>Pitcher, Ross G</creatorcontrib><creatorcontrib>Kramer, Michael J</creatorcontrib><title>Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Synthesis of 1-beta-D-ribofuranosyltetrazole and two 5-substituted derivatives, i.e., the 5-carboxamide and 5-acetamide, is described. The stereochemical structure of the parent tetrazole ribonucleoside has been established by means of nuclear Overhauser effect and x-ray crystallography. By analogy to the parent compound, the two 5-substituted tetrazole nucleosides are also assigned the beta configuration on the basis of the NMR coupling constant of the anomeric proton and the site of N-ribosylation is determined by 13C NMR studies. Results are also presented on antiviral testing of these synthetic tetrazole nucleosides against influenza A2/Asian/J-305 virus infection in mice.</description><subject>Animals</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - therapeutic use</subject><subject>Azoles - chemical synthesis</subject><subject>Crystallography</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mice</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Orthomyxoviridae Infections - drug therapy</subject><subject>Ribonucleosides - chemical synthesis</subject><subject>Ribonucleosides - therapeutic use</subject><subject>Tetrazoles - chemical synthesis</subject><subject>Tetrazoles - therapeutic use</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1976</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtL7TAUhYNc0eNj5PhCR9eBVHeSPtKhyPUBiuJj4iTstLveHHsab5KK-uvtoaIOHG1Y62Nt-Bjb4bDPQfCD-QJAiAyBFytsxnMBaaYg-8VmyzwVhZDrbCOEOQBILuQaW-MiqxRUM3Z589rHfxRsSFybRIoe31xHibfG9UPdkQu2oZBg3yQjZ31Cz9gNGK3rE1zm0T5bj12CD9THsMVWW-wCbX_cTXZ3_Pf26DQ9vzw5Ozo8T1HmWUyLElAaZaQCIDAc84ZDLUydK1lRW5kSm5I3si5VhVwRGZAtFyNmqOS8lZvsz7T75N3_gULUCxtq6jrsyQ1BKynzgqtqBPcmsPYuBE-tfvJ2gf5Vc9BLffqbvpH-_TE7mAU1X-zka-zTqbch0stnjf5RF6Usc317daPV_cn1BVzd64uR3514rIOeu8H3o5QfP78DcUCHXw</recordid><startdate>19760201</startdate><enddate>19760201</enddate><creator>Poonian, Mohindar S</creator><creator>Nowoswiat, Eugene F</creator><creator>Blount, John F</creator><creator>Williams, Thomas H</creator><creator>Pitcher, Ross G</creator><creator>Kramer, Michael J</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19760201</creationdate><title>Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents</title><author>Poonian, Mohindar S ; Nowoswiat, Eugene F ; Blount, John F ; Williams, Thomas H ; Pitcher, Ross G ; Kramer, Michael J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a354t-670a3b8b3800e0b1a5d10c2bc5839ef9b7ad71d3c789a18eeb03f12a5dbe711f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1976</creationdate><topic>Animals</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - therapeutic use</topic><topic>Azoles - chemical synthesis</topic><topic>Crystallography</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mice</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Orthomyxoviridae Infections - drug therapy</topic><topic>Ribonucleosides - chemical synthesis</topic><topic>Ribonucleosides - therapeutic use</topic><topic>Tetrazoles - chemical synthesis</topic><topic>Tetrazoles - therapeutic use</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Poonian, Mohindar S</creatorcontrib><creatorcontrib>Nowoswiat, Eugene F</creatorcontrib><creatorcontrib>Blount, John F</creatorcontrib><creatorcontrib>Williams, Thomas H</creatorcontrib><creatorcontrib>Pitcher, Ross G</creatorcontrib><creatorcontrib>Kramer, Michael J</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Poonian, Mohindar S</au><au>Nowoswiat, Eugene F</au><au>Blount, John F</au><au>Williams, Thomas H</au><au>Pitcher, Ross G</au><au>Kramer, Michael J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1976-02-01</date><risdate>1976</risdate><volume>19</volume><issue>2</issue><spage>286</spage><epage>290</epage><pages>286-290</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>Synthesis of 1-beta-D-ribofuranosyltetrazole and two 5-substituted derivatives, i.e., the 5-carboxamide and 5-acetamide, is described. The stereochemical structure of the parent tetrazole ribonucleoside has been established by means of nuclear Overhauser effect and x-ray crystallography. By analogy to the parent compound, the two 5-substituted tetrazole nucleosides are also assigned the beta configuration on the basis of the NMR coupling constant of the anomeric proton and the site of N-ribosylation is determined by 13C NMR studies. Results are also presented on antiviral testing of these synthetic tetrazole nucleosides against influenza A2/Asian/J-305 virus infection in mice.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>1249809</pmid><doi>10.1021/jm00224a016</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1976-02, Vol.19 (2), p.286-290 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_83356189 |
| source | MEDLINE; ACS Publications |
| subjects | Animals Antiviral Agents - chemical synthesis Antiviral Agents - therapeutic use Azoles - chemical synthesis Crystallography Magnetic Resonance Spectroscopy Mice Models, Molecular Molecular Conformation Orthomyxoviridae Infections - drug therapy Ribonucleosides - chemical synthesis Ribonucleosides - therapeutic use Tetrazoles - chemical synthesis Tetrazoles - therapeutic use |
| title | Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T02%3A17%3A52IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20tetrazole%20ribonucleosides%20and%20their%20evaluation%20as%20antiviral%20agents&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=Poonian,%20Mohindar%20S&rft.date=1976-02-01&rft.volume=19&rft.issue=2&rft.spage=286&rft.epage=290&rft.pages=286-290&rft.issn=0022-2623&rft.eissn=1520-4804&rft_id=info:doi/10.1021/jm00224a016&rft_dat=%3Cproquest_cross%3E83356189%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=83356189&rft_id=info:pmid/1249809&rfr_iscdi=true |