Derivatives of imidazotriazine and pyrrolotriazine C-nucleosides as potential new anti-HCV agents
[Display omitted] Previous investigations identified 2′-C-Me-branched ribo-C-nucleoside adenosine analogues, 1, which contains a pyrrolo[2,1-f][1,2,4]triazin-4-amine heterocyclic base, and 2, which contains an imidazo[2,1-f][1,2,4]triazin-4-amine heterocyclic base as two compounds with promising ant...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2014-11, Vol.24 (21), p.4984-4988 |
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| creator | Draffan, Alistair G. Frey, Barbara Fraser, Benjamin H. Pool, Brett Gannon, Carlie Tyndall, Edward M. Cianci, Julia Harding, Michael Lilly, Michael Hufton, Richard Halim, Rosliana Jahangiri, Saba Bond, Silas Jeynes, Tyrone P. Nguyen, Van T.T. Wirth, Veronika Luttick, Angela Tilmanis, Danielle Pryor, Melinda Porter, Kate Morton, Craig J. Lin, Bo Duan, Jianmin Bethell, Richard C. Kukolj, George Simoneau, Bruno Tucker, Simon P. |
| description | [Display omitted]
Previous investigations identified 2′-C-Me-branched ribo-C-nucleoside adenosine analogues, 1, which contains a pyrrolo[2,1-f][1,2,4]triazin-4-amine heterocyclic base, and 2, which contains an imidazo[2,1-f][1,2,4]triazin-4-amine heterocyclic base as two compounds with promising anti-HCV in vitro activity. This Letter describes the synthesis and evaluation of a series of novel analogues of these compounds substituted at the 2-, 7-, and 8-positions of the heterocyclic bases. A number of active new HCV inhibitors were identified but most compounds also demonstrated unacceptable cytotoxicity. However, the 7-fluoro analogue of 1 displayed good potency with a promising cytotherapeutic margin. |
| doi_str_mv | 10.1016/j.bmcl.2014.09.030 |
| format | Article |
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Previous investigations identified 2′-C-Me-branched ribo-C-nucleoside adenosine analogues, 1, which contains a pyrrolo[2,1-f][1,2,4]triazin-4-amine heterocyclic base, and 2, which contains an imidazo[2,1-f][1,2,4]triazin-4-amine heterocyclic base as two compounds with promising anti-HCV in vitro activity. This Letter describes the synthesis and evaluation of a series of novel analogues of these compounds substituted at the 2-, 7-, and 8-positions of the heterocyclic bases. A number of active new HCV inhibitors were identified but most compounds also demonstrated unacceptable cytotoxicity. However, the 7-fluoro analogue of 1 displayed good potency with a promising cytotherapeutic margin.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2014.09.030</identifier><identifier>PMID: 25288185</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antiviral ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; C-nucleoside ; Carcinoma, Hepatocellular - drug therapy ; Carcinoma, Hepatocellular - pathology ; Carcinoma, Hepatocellular - virology ; Cell Proliferation - drug effects ; Hepacivirus - drug effects ; Hepacivirus - genetics ; Hepatitis C ; Hepatitis C - drug therapy ; Hepatitis C - virology ; Hepatitis C virus ; Humans ; Imidazoles - chemistry ; Liver Neoplasms - drug therapy ; Liver Neoplasms - pathology ; Liver Neoplasms - virology ; Molecular Structure ; NS5B polymerase ; Nucleosides - chemistry ; Nucleosides - pharmacology ; Pyrroles - chemistry ; RNA, Viral - genetics ; Structure-Activity Relationship ; Triazines - chemistry ; Tumor Cells, Cultured ; Virus Replication - drug effects</subject><ispartof>Bioorganic & medicinal chemistry letters, 2014-11, Vol.24 (21), p.4984-4988</ispartof><rights>2014 Elsevier Ltd</rights><rights>Copyright © 2014 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-e972540d813a5e6d3fd9ea96dd82ef702ea44e70ffe8bc553062da34a8a0f36e3</citedby><cites>FETCH-LOGICAL-c389t-e972540d813a5e6d3fd9ea96dd82ef702ea44e70ffe8bc553062da34a8a0f36e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2014.09.030$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25288185$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Draffan, Alistair G.</creatorcontrib><creatorcontrib>Frey, Barbara</creatorcontrib><creatorcontrib>Fraser, Benjamin H.</creatorcontrib><creatorcontrib>Pool, Brett</creatorcontrib><creatorcontrib>Gannon, Carlie</creatorcontrib><creatorcontrib>Tyndall, Edward M.</creatorcontrib><creatorcontrib>Cianci, Julia</creatorcontrib><creatorcontrib>Harding, Michael</creatorcontrib><creatorcontrib>Lilly, Michael</creatorcontrib><creatorcontrib>Hufton, Richard</creatorcontrib><creatorcontrib>Halim, Rosliana</creatorcontrib><creatorcontrib>Jahangiri, Saba</creatorcontrib><creatorcontrib>Bond, Silas</creatorcontrib><creatorcontrib>Jeynes, Tyrone P.</creatorcontrib><creatorcontrib>Nguyen, Van T.T.</creatorcontrib><creatorcontrib>Wirth, Veronika</creatorcontrib><creatorcontrib>Luttick, Angela</creatorcontrib><creatorcontrib>Tilmanis, Danielle</creatorcontrib><creatorcontrib>Pryor, Melinda</creatorcontrib><creatorcontrib>Porter, Kate</creatorcontrib><creatorcontrib>Morton, Craig J.</creatorcontrib><creatorcontrib>Lin, Bo</creatorcontrib><creatorcontrib>Duan, Jianmin</creatorcontrib><creatorcontrib>Bethell, Richard C.</creatorcontrib><creatorcontrib>Kukolj, George</creatorcontrib><creatorcontrib>Simoneau, Bruno</creatorcontrib><creatorcontrib>Tucker, Simon P.</creatorcontrib><title>Derivatives of imidazotriazine and pyrrolotriazine C-nucleosides as potential new anti-HCV agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
Previous investigations identified 2′-C-Me-branched ribo-C-nucleoside adenosine analogues, 1, which contains a pyrrolo[2,1-f][1,2,4]triazin-4-amine heterocyclic base, and 2, which contains an imidazo[2,1-f][1,2,4]triazin-4-amine heterocyclic base as two compounds with promising anti-HCV in vitro activity. This Letter describes the synthesis and evaluation of a series of novel analogues of these compounds substituted at the 2-, 7-, and 8-positions of the heterocyclic bases. A number of active new HCV inhibitors were identified but most compounds also demonstrated unacceptable cytotoxicity. However, the 7-fluoro analogue of 1 displayed good potency with a promising cytotherapeutic margin.</description><subject>Antiviral</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>C-nucleoside</subject><subject>Carcinoma, Hepatocellular - drug therapy</subject><subject>Carcinoma, Hepatocellular - pathology</subject><subject>Carcinoma, Hepatocellular - virology</subject><subject>Cell Proliferation - drug effects</subject><subject>Hepacivirus - drug effects</subject><subject>Hepacivirus - genetics</subject><subject>Hepatitis C</subject><subject>Hepatitis C - drug therapy</subject><subject>Hepatitis C - virology</subject><subject>Hepatitis C virus</subject><subject>Humans</subject><subject>Imidazoles - chemistry</subject><subject>Liver Neoplasms - drug therapy</subject><subject>Liver Neoplasms - pathology</subject><subject>Liver Neoplasms - virology</subject><subject>Molecular Structure</subject><subject>NS5B polymerase</subject><subject>Nucleosides - chemistry</subject><subject>Nucleosides - pharmacology</subject><subject>Pyrroles - chemistry</subject><subject>RNA, Viral - genetics</subject><subject>Structure-Activity Relationship</subject><subject>Triazines - chemistry</subject><subject>Tumor Cells, Cultured</subject><subject>Virus Replication - drug effects</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkUuLFDEUhYMoTs_oH3AhtXRT5c2rOgE30j5GGHCj4i7cTm5JmqpKm1S3zPx60_SM7sTVhcP3ncU9jL3g0HHg_etdt5382AngqgPbgYRHbMVVr1qpQD9mK7A9tMaq7xfsspQdVBCUesouhBbGcKNXDN9Rjkdc4pFKk4YmTjHgXVpyxLs4U4NzaPa3Oafxb7Zp54MfKZUYqoSl2aeF5iXi2Mz0qypLbK833xr8UdPyjD0ZcCz0_P5esa8f3n_ZXLc3nz9-2ry9ab00dmnJroVWEAyXqKkPcgiW0PYhGEHDGgShUrSGYSCz9VpL6EVAqdAgDLInecVenXv3Of08UFncFIunccSZ0qE43ksNinMN_4EKa7XmylZUnFGfUymZBrfPccJ86zi40wpu504ruNMKDqyrK1Tp5X3_YTtR-KM8vL0Cb84A1YccI2VXfKTZU4iZ_OJCiv_q_w2SYpn2</recordid><startdate>20141101</startdate><enddate>20141101</enddate><creator>Draffan, Alistair G.</creator><creator>Frey, Barbara</creator><creator>Fraser, Benjamin H.</creator><creator>Pool, Brett</creator><creator>Gannon, Carlie</creator><creator>Tyndall, Edward M.</creator><creator>Cianci, Julia</creator><creator>Harding, Michael</creator><creator>Lilly, Michael</creator><creator>Hufton, Richard</creator><creator>Halim, Rosliana</creator><creator>Jahangiri, Saba</creator><creator>Bond, Silas</creator><creator>Jeynes, Tyrone P.</creator><creator>Nguyen, Van T.T.</creator><creator>Wirth, Veronika</creator><creator>Luttick, Angela</creator><creator>Tilmanis, Danielle</creator><creator>Pryor, Melinda</creator><creator>Porter, Kate</creator><creator>Morton, Craig J.</creator><creator>Lin, Bo</creator><creator>Duan, Jianmin</creator><creator>Bethell, Richard C.</creator><creator>Kukolj, George</creator><creator>Simoneau, Bruno</creator><creator>Tucker, Simon P.</creator><general>Elsevier Ltd</general><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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20141101</creationdate><title>Derivatives of imidazotriazine and pyrrolotriazine C-nucleosides as potential new anti-HCV agents</title><author>Draffan, Alistair G. ; Frey, Barbara ; Fraser, Benjamin H. ; Pool, Brett ; Gannon, Carlie ; Tyndall, Edward M. ; Cianci, Julia ; Harding, Michael ; Lilly, Michael ; Hufton, Richard ; Halim, Rosliana ; Jahangiri, Saba ; Bond, Silas ; Jeynes, Tyrone P. ; Nguyen, Van T.T. ; Wirth, Veronika ; Luttick, Angela ; Tilmanis, Danielle ; Pryor, Melinda ; Porter, Kate ; Morton, Craig J. ; Lin, Bo ; Duan, Jianmin ; Bethell, Richard C. ; Kukolj, George ; Simoneau, Bruno ; Tucker, Simon P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-e972540d813a5e6d3fd9ea96dd82ef702ea44e70ffe8bc553062da34a8a0f36e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Antiviral</topic><topic>Antiviral Agents - 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Previous investigations identified 2′-C-Me-branched ribo-C-nucleoside adenosine analogues, 1, which contains a pyrrolo[2,1-f][1,2,4]triazin-4-amine heterocyclic base, and 2, which contains an imidazo[2,1-f][1,2,4]triazin-4-amine heterocyclic base as two compounds with promising anti-HCV in vitro activity. This Letter describes the synthesis and evaluation of a series of novel analogues of these compounds substituted at the 2-, 7-, and 8-positions of the heterocyclic bases. A number of active new HCV inhibitors were identified but most compounds also demonstrated unacceptable cytotoxicity. However, the 7-fluoro analogue of 1 displayed good potency with a promising cytotherapeutic margin.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>25288185</pmid><doi>10.1016/j.bmcl.2014.09.030</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2014-11, Vol.24 (21), p.4984-4988 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1635041150 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Antiviral Antiviral Agents - chemistry Antiviral Agents - pharmacology C-nucleoside Carcinoma, Hepatocellular - drug therapy Carcinoma, Hepatocellular - pathology Carcinoma, Hepatocellular - virology Cell Proliferation - drug effects Hepacivirus - drug effects Hepacivirus - genetics Hepatitis C Hepatitis C - drug therapy Hepatitis C - virology Hepatitis C virus Humans Imidazoles - chemistry Liver Neoplasms - drug therapy Liver Neoplasms - pathology Liver Neoplasms - virology Molecular Structure NS5B polymerase Nucleosides - chemistry Nucleosides - pharmacology Pyrroles - chemistry RNA, Viral - genetics Structure-Activity Relationship Triazines - chemistry Tumor Cells, Cultured Virus Replication - drug effects |
| title | Derivatives of imidazotriazine and pyrrolotriazine C-nucleosides as potential new anti-HCV agents |
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