An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents
We report the synthesis of three novel fluoro-thiofuranosyl nucleosides. These novel synthesized molecules have a promising potential as antitumor and anti-rotavirus agents. 1,2:5,6-Di- O-isopropylidene-α- d-glucofuranose by the sequence of mild oxidation, reduction, fluorination, periodate oxidatio...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2007-05, Vol.15 (9), p.3241-3247 |
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| creator | Tsoukala, Evangelia Agelis, George Dolinšek, Jan Botić, Tanja Cencič, Avrelija Komiotis, Dimitri |
| description | We report the synthesis of three novel fluoro-thiofuranosyl nucleosides. These novel synthesized molecules have a promising potential as antitumor and anti-rotavirus agents.
1,2:5,6-Di-
O-isopropylidene-α-
d-glucofuranose by the sequence of mild oxidation, reduction, fluorination, periodate oxidation, borohydride reduction, and sulfonylation gave 3-deoxy-3-fluoro-1,2-
O-isopropylidene-5-
O-
p-toluenesulfonyl-α-
d-xylofuranose (
5). Tosylate
5 was converted to thioacetate derivative
6, which after acetolysis gave 1,2-di-
O-acetyl-5-
S-acetyl-3-deoxy-3-fluoro-5-thio-
d-xylofuranose (
7). Condensation of
7 with silylated thymine, uracil, and 5-fluorouracil afforded nucleosides 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) thymine (
8), 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) uracil (
9), and 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) 5-fluorouracil (
10). Compounds
8,
9, and
10 are biologically active against rotavirus infection and the growth of tumor cells. |
| doi_str_mv | 10.1016/j.bmc.2007.02.031 |
| format | Article |
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1,2:5,6-Di-
O-isopropylidene-α-
d-glucofuranose by the sequence of mild oxidation, reduction, fluorination, periodate oxidation, borohydride reduction, and sulfonylation gave 3-deoxy-3-fluoro-1,2-
O-isopropylidene-5-
O-
p-toluenesulfonyl-α-
d-xylofuranose (
5). Tosylate
5 was converted to thioacetate derivative
6, which after acetolysis gave 1,2-di-
O-acetyl-5-
S-acetyl-3-deoxy-3-fluoro-5-thio-
d-xylofuranose (
7). Condensation of
7 with silylated thymine, uracil, and 5-fluorouracil afforded nucleosides 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) thymine (
8), 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) uracil (
9), and 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) 5-fluorouracil (
10). Compounds
8,
9, and
10 are biologically active against rotavirus infection and the growth of tumor cells.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2007.02.031</identifier><identifier>PMID: 17337193</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>3-Deoxy-3-fluoro-5-thio-xylofuranose ; 5-Fluorouracil ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antitumor agent ; Antiviral ; Antiviral agents ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Biological and medical sciences ; Caco-2 Cells ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Drug Screening Assays, Antitumor ; Fluorouracil - chemistry ; General aspects ; Humans ; Intestines - cytology ; Intestines - drug effects ; Medical sciences ; Microbial Sensitivity Tests ; Molecular Structure ; Nucleoside ; Nucleosides - chemical synthesis ; Nucleosides - chemistry ; Nucleosides - pharmacology ; Pharmacology. Drug treatments ; Rotavirus - drug effects ; Stereoisomerism ; Structure-Activity Relationship ; Thymine ; Thymine - chemistry ; Uracil ; Uracil - chemistry ; Xylose - analogs & derivatives ; Xylose - chemistry ; Zidovudine - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry, 2007-05, Vol.15 (9), p.3241-3247</ispartof><rights>2007 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c447t-5a695bd1e6a8b716c4674890695e41efba0c4c013bd70c86a9ffb762007a34a23</citedby><cites>FETCH-LOGICAL-c447t-5a695bd1e6a8b716c4674890695e41efba0c4c013bd70c86a9ffb762007a34a23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089607001526$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18658116$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17337193$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tsoukala, Evangelia</creatorcontrib><creatorcontrib>Agelis, George</creatorcontrib><creatorcontrib>Dolinšek, Jan</creatorcontrib><creatorcontrib>Botić, Tanja</creatorcontrib><creatorcontrib>Cencič, Avrelija</creatorcontrib><creatorcontrib>Komiotis, Dimitri</creatorcontrib><title>An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>We report the synthesis of three novel fluoro-thiofuranosyl nucleosides. These novel synthesized molecules have a promising potential as antitumor and anti-rotavirus agents.
1,2:5,6-Di-
O-isopropylidene-α-
d-glucofuranose by the sequence of mild oxidation, reduction, fluorination, periodate oxidation, borohydride reduction, and sulfonylation gave 3-deoxy-3-fluoro-1,2-
O-isopropylidene-5-
O-
p-toluenesulfonyl-α-
d-xylofuranose (
5). Tosylate
5 was converted to thioacetate derivative
6, which after acetolysis gave 1,2-di-
O-acetyl-5-
S-acetyl-3-deoxy-3-fluoro-5-thio-
d-xylofuranose (
7). Condensation of
7 with silylated thymine, uracil, and 5-fluorouracil afforded nucleosides 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) thymine (
8), 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) uracil (
9), and 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) 5-fluorouracil (
10). Compounds
8,
9, and
10 are biologically active against rotavirus infection and the growth of tumor cells.</description><subject>3-Deoxy-3-fluoro-5-thio-xylofuranose</subject><subject>5-Fluorouracil</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antitumor agent</subject><subject>Antiviral</subject><subject>Antiviral agents</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Caco-2 Cells</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fluorouracil - chemistry</subject><subject>General aspects</subject><subject>Humans</subject><subject>Intestines - cytology</subject><subject>Intestines - drug effects</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Nucleoside</subject><subject>Nucleosides - chemical synthesis</subject><subject>Nucleosides - chemistry</subject><subject>Nucleosides - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Rotavirus - drug effects</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Thymine</subject><subject>Thymine - chemistry</subject><subject>Uracil</subject><subject>Uracil - chemistry</subject><subject>Xylose - analogs & derivatives</subject><subject>Xylose - chemistry</subject><subject>Zidovudine - pharmacology</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc1u1DAUhS0EokPhAdggb2DVpNexYydiVVXlR6rEBtaW41wzHiXxYCdV8yi8LU5npO5YXfn4u8fWOYS8Z1AyYPL6UHajLSsAVUJVAmcvyI4JKQrOW_aS7KCVTQFNKy_Im5QOAFCJlr0mF0xxrljLd-TvzUTROW89TjNN6zTvMflEg6O8cMMSYijqYt77UDyuQ3BLNFNI60CnxQ4Yku_xCZ736-gnvKIZsH64ombqaX12OGnUJHoMc37Hm3zIY17GEGmI1xu8CQ8-ble_M5PeklfODAnfnecl-fXl7uftt-L-x9fvtzf3hRVCzUVtZFt3PUNpmk4xaYVUomkhqygYus6AFRYY73oFtpGmda5TcgvNcGEqfkk-nXyPMfxZMM169MniMJgJw5K0Al7VCjaQnUAbQ0oRnT5GP5q4agZ660MfdO5Db9YaKp37yDsfzuZLN2L_vHEuIAMfz4BJ1gwux2t9euYaWTeMycx9PnGYo3jwGHXaKrPY-4h21n3w__nGPz6NquA</recordid><startdate>20070501</startdate><enddate>20070501</enddate><creator>Tsoukala, Evangelia</creator><creator>Agelis, George</creator><creator>Dolinšek, Jan</creator><creator>Botić, Tanja</creator><creator>Cencič, Avrelija</creator><creator>Komiotis, Dimitri</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><scope>IQODW</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>20070501</creationdate><title>An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents</title><author>Tsoukala, Evangelia ; Agelis, George ; Dolinšek, Jan ; Botić, Tanja ; Cencič, Avrelija ; Komiotis, Dimitri</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c447t-5a695bd1e6a8b716c4674890695e41efba0c4c013bd70c86a9ffb762007a34a23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>3-Deoxy-3-fluoro-5-thio-xylofuranose</topic><topic>5-Fluorouracil</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antitumor agent</topic><topic>Antiviral</topic><topic>Antiviral agents</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Caco-2 Cells</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fluorouracil - chemistry</topic><topic>General aspects</topic><topic>Humans</topic><topic>Intestines - cytology</topic><topic>Intestines - drug effects</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Nucleoside</topic><topic>Nucleosides - chemical synthesis</topic><topic>Nucleosides - chemistry</topic><topic>Nucleosides - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Rotavirus - drug effects</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>Thymine</topic><topic>Thymine - chemistry</topic><topic>Uracil</topic><topic>Uracil - chemistry</topic><topic>Xylose - analogs & derivatives</topic><topic>Xylose - chemistry</topic><topic>Zidovudine - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tsoukala, Evangelia</creatorcontrib><creatorcontrib>Agelis, George</creatorcontrib><creatorcontrib>Dolinšek, Jan</creatorcontrib><creatorcontrib>Botić, Tanja</creatorcontrib><creatorcontrib>Cencič, Avrelija</creatorcontrib><creatorcontrib>Komiotis, Dimitri</creatorcontrib><collection>Pascal-Francis</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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tsoukala, Evangelia</au><au>Agelis, George</au><au>Dolinšek, Jan</au><au>Botić, Tanja</au><au>Cencič, Avrelija</au><au>Komiotis, Dimitri</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2007-05-01</date><risdate>2007</risdate><volume>15</volume><issue>9</issue><spage>3241</spage><epage>3247</epage><pages>3241-3247</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>We report the synthesis of three novel fluoro-thiofuranosyl nucleosides. These novel synthesized molecules have a promising potential as antitumor and anti-rotavirus agents.
1,2:5,6-Di-
O-isopropylidene-α-
d-glucofuranose by the sequence of mild oxidation, reduction, fluorination, periodate oxidation, borohydride reduction, and sulfonylation gave 3-deoxy-3-fluoro-1,2-
O-isopropylidene-5-
O-
p-toluenesulfonyl-α-
d-xylofuranose (
5). Tosylate
5 was converted to thioacetate derivative
6, which after acetolysis gave 1,2-di-
O-acetyl-5-
S-acetyl-3-deoxy-3-fluoro-5-thio-
d-xylofuranose (
7). Condensation of
7 with silylated thymine, uracil, and 5-fluorouracil afforded nucleosides 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) thymine (
8), 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) uracil (
9), and 1-(5-
S-acetyl-3-deoxy-3-fluoro-5-thio-β-
d-xylofuranosyl) 5-fluorouracil (
10). Compounds
8,
9, and
10 are biologically active against rotavirus infection and the growth of tumor cells.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>17337193</pmid><doi>10.1016/j.bmc.2007.02.031</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2007-05, Vol.15 (9), p.3241-3247 |
| issn | 0968-0896 1464-3391 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_70325702 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | 3-Deoxy-3-fluoro-5-thio-xylofuranose 5-Fluorouracil Antibiotics. Antiinfectious agents. Antiparasitic agents Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antitumor agent Antiviral Antiviral agents Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Biological and medical sciences Caco-2 Cells Cell Line, Tumor Cell Proliferation - drug effects Drug Screening Assays, Antitumor Fluorouracil - chemistry General aspects Humans Intestines - cytology Intestines - drug effects Medical sciences Microbial Sensitivity Tests Molecular Structure Nucleoside Nucleosides - chemical synthesis Nucleosides - chemistry Nucleosides - pharmacology Pharmacology. Drug treatments Rotavirus - drug effects Stereoisomerism Structure-Activity Relationship Thymine Thymine - chemistry Uracil Uracil - chemistry Xylose - analogs & derivatives Xylose - chemistry Zidovudine - pharmacology |
| title | An efficient synthesis of 3-fluoro-5-thio-xylofuranosyl nucleosides of thymine, uracil, and 5-fluorouracil as potential antitumor or/and antiviral agents |
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