Synthesis and cytotoxic activity of novel 10-alkylated docetaxel analogs
An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7- O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analo...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 1998-03, Vol.8 (5), p.427-432 |
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| container_issue | 5 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Nakayama, Kiyoshi Terasawa, Hirofumi Mitsui, Ikuo Ohsuki, Satoru Uoto, Kouichi Iimura, Shin Soga, Tsunehiko |
| description | An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7-
O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel.
An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7-
O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel. |
| doi_str_mv | 10.1016/S0960-894X(98)00040-7 |
| format | Article |
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O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel.
An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7-
O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(98)00040-7</identifier><identifier>PMID: 9871592</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Alkylation ; Antineoplastic agents ; Antineoplastic Agents, Phytogenic - chemical synthesis ; Antineoplastic Agents, Phytogenic - pharmacology ; Biological and medical sciences ; Docetaxel ; General aspects ; Medical sciences ; Models, Molecular ; Paclitaxel - analogs & derivatives ; Paclitaxel - chemical synthesis ; Paclitaxel - chemistry ; Paclitaxel - pharmacology ; Pharmacology. Drug treatments ; Taxoids ; Tumor Cells, Cultured</subject><ispartof>Bioorganic & medicinal chemistry letters, 1998-03, Vol.8 (5), p.427-432</ispartof><rights>1998</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-9df693a026f29b1eb82910e2b40ac96a0c32330d5cbc933e0fd6e5f318af200b3</citedby><cites>FETCH-LOGICAL-c389t-9df693a026f29b1eb82910e2b40ac96a0c32330d5cbc933e0fd6e5f318af200b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X98000407$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2180251$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9871592$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nakayama, Kiyoshi</creatorcontrib><creatorcontrib>Terasawa, Hirofumi</creatorcontrib><creatorcontrib>Mitsui, Ikuo</creatorcontrib><creatorcontrib>Ohsuki, Satoru</creatorcontrib><creatorcontrib>Uoto, Kouichi</creatorcontrib><creatorcontrib>Iimura, Shin</creatorcontrib><creatorcontrib>Soga, Tsunehiko</creatorcontrib><title>Synthesis and cytotoxic activity of novel 10-alkylated docetaxel analogs</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7-
O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel.
An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7-
O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel.</description><subject>Alkylation</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents, Phytogenic - chemical synthesis</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Docetaxel</subject><subject>General aspects</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Paclitaxel - analogs & derivatives</subject><subject>Paclitaxel - chemical synthesis</subject><subject>Paclitaxel - chemistry</subject><subject>Paclitaxel - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Taxoids</subject><subject>Tumor Cells, Cultured</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1r3DAQhkVoSLdJfkLAh1LSg5vRh73WqYQlH4WFHJJCbmIsjVq1Xiu1tMv639fJLnvNaWDmeWeGh7ELDt848PrqEXQNZaPV86VuvgKAgnJ-xGZc1aqUCqoPbHZAPrJPKf0B4AqUOmEnupnzSosZu38c-_ybUkgF9q6wY445boMt0OawCXksoi_6uKGu4FBi93fsMJMrXLSUcTu1sccu_kpn7Nhjl-h8X0_Zz9ubp8V9uXy4-7G4XpZWNjqX2vlaSwRRe6FbTm0jNAcSrQK0ukawUkgJrrKt1VISeFdT5SVv0AuAVp6yL7u9L0P8t6aUzSokS12HPcV1MrXmfF5xMYHVDrRDTGkgb16GsMJhNBzMq0HzZtC86jG6MW8GzXzKXewPrNsVuUNqr2yaf97PMVns_IC9DemACd6AqPiEfd9hNMnYBBpMsoF6Sy4MZLNxMbzzyH-gGY13</recordid><startdate>19980303</startdate><enddate>19980303</enddate><creator>Nakayama, Kiyoshi</creator><creator>Terasawa, Hirofumi</creator><creator>Mitsui, Ikuo</creator><creator>Ohsuki, Satoru</creator><creator>Uoto, Kouichi</creator><creator>Iimura, Shin</creator><creator>Soga, Tsunehiko</creator><general>Elsevier Ltd</general><general>Elsevier</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>19980303</creationdate><title>Synthesis and cytotoxic activity of novel 10-alkylated docetaxel analogs</title><author>Nakayama, Kiyoshi ; Terasawa, Hirofumi ; Mitsui, Ikuo ; Ohsuki, Satoru ; Uoto, Kouichi ; Iimura, Shin ; Soga, Tsunehiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-9df693a026f29b1eb82910e2b40ac96a0c32330d5cbc933e0fd6e5f318af200b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>Alkylation</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents, Phytogenic - chemical synthesis</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Docetaxel</topic><topic>General aspects</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Paclitaxel - analogs & derivatives</topic><topic>Paclitaxel - chemical synthesis</topic><topic>Paclitaxel - chemistry</topic><topic>Paclitaxel - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Taxoids</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nakayama, Kiyoshi</creatorcontrib><creatorcontrib>Terasawa, Hirofumi</creatorcontrib><creatorcontrib>Mitsui, Ikuo</creatorcontrib><creatorcontrib>Ohsuki, Satoru</creatorcontrib><creatorcontrib>Uoto, Kouichi</creatorcontrib><creatorcontrib>Iimura, Shin</creatorcontrib><creatorcontrib>Soga, Tsunehiko</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 letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nakayama, Kiyoshi</au><au>Terasawa, Hirofumi</au><au>Mitsui, Ikuo</au><au>Ohsuki, Satoru</au><au>Uoto, Kouichi</au><au>Iimura, Shin</au><au>Soga, Tsunehiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and cytotoxic activity of novel 10-alkylated docetaxel analogs</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>1998-03-03</date><risdate>1998</risdate><volume>8</volume><issue>5</issue><spage>427</spage><epage>432</epage><pages>427-432</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7-
O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel.
An alkylation method of docetaxel at the C-10 position has been established by a radical coupling reaction using a 10-xanthate derivative of 7-
O-TES-10-deacetylbaccatin III and appropriate alkenes. In addition the cytotoxic activity of 10-alkylated docetaxel analogs was evaluated. Among these analogs, a derivative having a methoxycarbonyl group at the end of the alkyl moiety exhibited more potent cytotoxic activity than docetaxel.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>9871592</pmid><doi>10.1016/S0960-894X(98)00040-7</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 1998-03, Vol.8 (5), p.427-432 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Alkylation Antineoplastic agents Antineoplastic Agents, Phytogenic - chemical synthesis Antineoplastic Agents, Phytogenic - pharmacology Biological and medical sciences Docetaxel General aspects Medical sciences Models, Molecular Paclitaxel - analogs & derivatives Paclitaxel - chemical synthesis Paclitaxel - chemistry Paclitaxel - pharmacology Pharmacology. Drug treatments Taxoids Tumor Cells, Cultured |
| title | Synthesis and cytotoxic activity of novel 10-alkylated docetaxel analogs |
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