Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides
An efficient and facile synthesis of a large series of diverse 6-[2-(dialkylamino)vinyl]-, 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, and 6-[2-(alkylsulfanyl)ethyl]purine nucleosides (35 examples of both ribo- and 2′-deoxyribonucleosides) was developed. The key transformations involved conjugat...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2008-02, Vol.16 (3), p.1400-1424 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Kuchař, Martin Hocek, Michal Pohl, Radek Votruba, Ivan Shih, I-hung Mabery, Eric Mackman, Richard |
| description | An efficient and facile synthesis of a large series of diverse 6-[2-(dialkylamino)vinyl]-, 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, and 6-[2-(alkylsulfanyl)ethyl]purine nucleosides (35 examples of both ribo- and 2′-deoxyribonucleosides) was developed. The key transformations involved conjugate nucleophilic additions of amines, alcoholates, or thiolates to Tol-protected 6-alkylylpurine or 6-vinylpurine nucleosides. 6-[(2-Dialkylamino)vinyl]- and some 6-[(2-dialkylamino)ethyl]purine ribonucleosides exerted significant cytostatic effects and some anti-HCV activity with low selectivity. |
| doi_str_mv | 10.1016/j.bmc.2007.10.063 |
| format | Article |
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The key transformations involved conjugate nucleophilic additions of amines, alcoholates, or thiolates to Tol-protected 6-alkylylpurine or 6-vinylpurine nucleosides. 6-[(2-Dialkylamino)vinyl]- and some 6-[(2-dialkylamino)ethyl]purine ribonucleosides exerted significant cytostatic effects and some anti-HCV activity with low selectivity.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2007.10.063</identifier><identifier>PMID: 17997319</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Alkylation ; Amination ; Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antineoplastic agents ; Antiviral Agents ; Biological and medical sciences ; Cell Line ; Cell Survival - drug effects ; Conjugate additions ; Cytostatic activity ; General aspects ; Hepacivirus - drug effects ; Humans ; Medical sciences ; Mice ; Molecular Structure ; Nucleosides ; Pharmacology. Drug treatments ; Purine Nucleosides - chemical synthesis ; Purine Nucleosides - chemistry ; Purine Nucleosides - pharmacology ; Purines ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry, 2008-02, Vol.16 (3), p.1400-1424</ispartof><rights>2007 Elsevier Ltd</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-285e9728ed22c4df711e556137c74056d6ef657c114fc82934a4f72114a9c9a63</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089607009327$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20082214$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17997319$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kuchař, Martin</creatorcontrib><creatorcontrib>Hocek, Michal</creatorcontrib><creatorcontrib>Pohl, Radek</creatorcontrib><creatorcontrib>Votruba, Ivan</creatorcontrib><creatorcontrib>Shih, I-hung</creatorcontrib><creatorcontrib>Mabery, Eric</creatorcontrib><creatorcontrib>Mackman, Richard</creatorcontrib><title>Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>An efficient and facile synthesis of a large series of diverse 6-[2-(dialkylamino)vinyl]-, 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, and 6-[2-(alkylsulfanyl)ethyl]purine nucleosides (35 examples of both ribo- and 2′-deoxyribonucleosides) was developed. The key transformations involved conjugate nucleophilic additions of amines, alcoholates, or thiolates to Tol-protected 6-alkylylpurine or 6-vinylpurine nucleosides. 6-[(2-Dialkylamino)vinyl]- and some 6-[(2-dialkylamino)ethyl]purine ribonucleosides exerted significant cytostatic effects and some anti-HCV activity with low selectivity.</description><subject>Alkylation</subject><subject>Amination</subject><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antineoplastic agents</subject><subject>Antiviral Agents</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Cell Survival - drug effects</subject><subject>Conjugate additions</subject><subject>Cytostatic activity</subject><subject>General aspects</subject><subject>Hepacivirus - drug effects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Nucleosides</subject><subject>Pharmacology. Drug treatments</subject><subject>Purine Nucleosides - chemical synthesis</subject><subject>Purine Nucleosides - chemistry</subject><subject>Purine Nucleosides - pharmacology</subject><subject>Purines</subject><subject>Structure-Activity Relationship</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc2KFDEUhYMoTjv6AG6kNsoMdLX5q6SCKxn8gwEX6kqGkEndYtKmkjapaqzn8gVNdTfjRlyE5J773ZOQg9BzgjcEE_F6u7kd7IZiLEu9wYI9QCvCBa8ZU-QhWmEl2hq3SpyhJzlvMcaUK_IYnRGplGRErdDvL3MY7yC7vK7sPMY8mtHZdWVCV9bo9i4ZXxm7nMa5in0V4h58JervtL7onPE_Zm8GF-IljHezv6nXpXdB69KIv-aDdnnQFv5A58n3JhT5fmC57B-Ge1eom92UXIAqTNZDzK6D_BQ96o3P8Oy0n6Nv7999vfpYX3_-8Onq7XVtWUvGmrYNKElb6Ci1vOslIdA0gjBpJceN6AT0opGWEN7blirGDe8lLaVRVhnBztGro-8uxZ8T5FEPLlvw3gSIU9YSMy6ZaApIjqBNMecEvd4lN5g0a4L1kpTe6pKUXpJapJJUmXlxMp9uB-j-TpyiKcDLE2CyNb5PJliX77ni1VJKeOHeHDkoX7F3kHS2DoKFziWwo-6i-88z_gBxArEi</recordid><startdate>20080201</startdate><enddate>20080201</enddate><creator>Kuchař, Martin</creator><creator>Hocek, Michal</creator><creator>Pohl, Radek</creator><creator>Votruba, Ivan</creator><creator>Shih, I-hung</creator><creator>Mabery, Eric</creator><creator>Mackman, Richard</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>20080201</creationdate><title>Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides</title><author>Kuchař, Martin ; Hocek, Michal ; Pohl, Radek ; Votruba, Ivan ; Shih, I-hung ; Mabery, Eric ; Mackman, Richard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-285e9728ed22c4df711e556137c74056d6ef657c114fc82934a4f72114a9c9a63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Alkylation</topic><topic>Amination</topic><topic>Animals</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antineoplastic agents</topic><topic>Antiviral Agents</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Cell Survival - drug effects</topic><topic>Conjugate additions</topic><topic>Cytostatic activity</topic><topic>General aspects</topic><topic>Hepacivirus - drug effects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Nucleosides</topic><topic>Pharmacology. Drug treatments</topic><topic>Purine Nucleosides - chemical synthesis</topic><topic>Purine Nucleosides - chemistry</topic><topic>Purine Nucleosides - pharmacology</topic><topic>Purines</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kuchař, Martin</creatorcontrib><creatorcontrib>Hocek, Michal</creatorcontrib><creatorcontrib>Pohl, Radek</creatorcontrib><creatorcontrib>Votruba, Ivan</creatorcontrib><creatorcontrib>Shih, I-hung</creatorcontrib><creatorcontrib>Mabery, Eric</creatorcontrib><creatorcontrib>Mackman, Richard</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>Kuchař, Martin</au><au>Hocek, Michal</au><au>Pohl, Radek</au><au>Votruba, Ivan</au><au>Shih, I-hung</au><au>Mabery, Eric</au><au>Mackman, Richard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2008-02-01</date><risdate>2008</risdate><volume>16</volume><issue>3</issue><spage>1400</spage><epage>1424</epage><pages>1400-1424</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>An efficient and facile synthesis of a large series of diverse 6-[2-(dialkylamino)vinyl]-, 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, and 6-[2-(alkylsulfanyl)ethyl]purine nucleosides (35 examples of both ribo- and 2′-deoxyribonucleosides) was developed. The key transformations involved conjugate nucleophilic additions of amines, alcoholates, or thiolates to Tol-protected 6-alkylylpurine or 6-vinylpurine nucleosides. 6-[(2-Dialkylamino)vinyl]- and some 6-[(2-dialkylamino)ethyl]purine ribonucleosides exerted significant cytostatic effects and some anti-HCV activity with low selectivity.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>17997319</pmid><doi>10.1016/j.bmc.2007.10.063</doi><tpages>25</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2008-02, Vol.16 (3), p.1400-1424 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Alkylation Amination Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antineoplastic agents Antiviral Agents Biological and medical sciences Cell Line Cell Survival - drug effects Conjugate additions Cytostatic activity General aspects Hepacivirus - drug effects Humans Medical sciences Mice Molecular Structure Nucleosides Pharmacology. Drug treatments Purine Nucleosides - chemical synthesis Purine Nucleosides - chemistry Purine Nucleosides - pharmacology Purines Structure-Activity Relationship |
| title | Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides |
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