Chemical synthesis of febrifugine and analogues
[Display omitted] The quinazolinone-containing 2,3-disubstituted piperidines febrifugine and isofebrifugine have been the subject of significant research efforts since their occurrence in Dichroa febrifuga and their anti-malarial actions were first described in the late 1940s. Subsequently they have...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2018-05, Vol.26 (9), p.2199-2220 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Smullen, Shaun McLaughlin, Noel P. Evans, Paul |
| description | [Display omitted]
The quinazolinone-containing 2,3-disubstituted piperidines febrifugine and isofebrifugine have been the subject of significant research efforts since their occurrence in Dichroa febrifuga and their anti-malarial actions were first described in the late 1940s. Subsequently they have also been shown to be present in other plants belonging to the hydrangea family and various analogues of febrifugine have been prepared in attempts to tune biological properties. The most notable analogue is termed halofuginone and a substantial body of work now demonstrates that this compound possesses potent human disease relevant activities. This review focuses on the literature associated with efforts dedicated towards uncovering the structures of febrifugine and isofebrifugine, the development of practical methods for their synthesis and the syntheses of structural analogues. |
| doi_str_mv | 10.1016/j.bmc.2018.04.027 |
| format | Article |
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The quinazolinone-containing 2,3-disubstituted piperidines febrifugine and isofebrifugine have been the subject of significant research efforts since their occurrence in Dichroa febrifuga and their anti-malarial actions were first described in the late 1940s. Subsequently they have also been shown to be present in other plants belonging to the hydrangea family and various analogues of febrifugine have been prepared in attempts to tune biological properties. The most notable analogue is termed halofuginone and a substantial body of work now demonstrates that this compound possesses potent human disease relevant activities. This review focuses on the literature associated with efforts dedicated towards uncovering the structures of febrifugine and isofebrifugine, the development of practical methods for their synthesis and the syntheses of structural analogues.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2018.04.027</identifier><identifier>PMID: 29681487</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>3-hydroxypiperidine ; Animals ; Anti-angiogenic ; Anti-fibrotic ; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis ; Anti-Inflammatory Agents, Non-Steroidal - chemistry ; Anti-Inflammatory Agents, Non-Steroidal - pharmacology ; Anti-protozoal ; Antimalarials - chemical synthesis ; Antimalarials - chemistry ; Antimalarials - pharmacology ; Cyclization ; Cycloaddition Reaction ; Dichroine A and B ; Febrifugine ; Halofuginone ; Humans ; Isofebrifugine ; Isomerization ; Piperidines - chemical synthesis ; Piperidines - chemistry ; Piperidines - pharmacology ; Plasmodium falciparum - drug effects ; Quinazolines - chemical synthesis ; Quinazolines - chemistry ; Quinazolines - pharmacology ; Quinazolinone ; Quinazolinones - chemical synthesis ; Quinazolinones - chemistry ; Quinazolinones - pharmacology ; Stereoisomerism</subject><ispartof>Bioorganic & medicinal chemistry, 2018-05, Vol.26 (9), p.2199-2220</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright © 2018 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c353t-f7a17fe7cd6c5433a96dc06ad2bdf437e9223382c0eb760ddb329e3f2af1b2d83</citedby><cites>FETCH-LOGICAL-c353t-f7a17fe7cd6c5433a96dc06ad2bdf437e9223382c0eb760ddb329e3f2af1b2d83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2018.04.027$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29681487$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Smullen, Shaun</creatorcontrib><creatorcontrib>McLaughlin, Noel P.</creatorcontrib><creatorcontrib>Evans, Paul</creatorcontrib><title>Chemical synthesis of febrifugine and analogues</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted]
The quinazolinone-containing 2,3-disubstituted piperidines febrifugine and isofebrifugine have been the subject of significant research efforts since their occurrence in Dichroa febrifuga and their anti-malarial actions were first described in the late 1940s. Subsequently they have also been shown to be present in other plants belonging to the hydrangea family and various analogues of febrifugine have been prepared in attempts to tune biological properties. The most notable analogue is termed halofuginone and a substantial body of work now demonstrates that this compound possesses potent human disease relevant activities. This review focuses on the literature associated with efforts dedicated towards uncovering the structures of febrifugine and isofebrifugine, the development of practical methods for their synthesis and the syntheses of structural analogues.</description><subject>3-hydroxypiperidine</subject><subject>Animals</subject><subject>Anti-angiogenic</subject><subject>Anti-fibrotic</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemistry</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</subject><subject>Anti-protozoal</subject><subject>Antimalarials - chemical synthesis</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - pharmacology</subject><subject>Cyclization</subject><subject>Cycloaddition Reaction</subject><subject>Dichroine A and B</subject><subject>Febrifugine</subject><subject>Halofuginone</subject><subject>Humans</subject><subject>Isofebrifugine</subject><subject>Isomerization</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Piperidines - pharmacology</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Quinazolines - chemical synthesis</subject><subject>Quinazolines - chemistry</subject><subject>Quinazolines - pharmacology</subject><subject>Quinazolinone</subject><subject>Quinazolinones - chemical synthesis</subject><subject>Quinazolinones - chemistry</subject><subject>Quinazolinones - pharmacology</subject><subject>Stereoisomerism</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kDtPAzEQhC0EIiHwA2jQlTR38Su-s6hQxEuKRAO15bPXiaN7BPsOKf8eRwmUFKstdmZW8yF0S3BBMBHzbVG3pqCYVAXmBablGZoSLnjOmCTnaIqlqHJcSTFBVzFuMcaUS3KJJjQdCK_KKZovN9B6o5ss7rthA9HHrHeZgzp4N659B5nubBrd9OsR4jW6cLqJcHPaM_T5_PSxfM1X7y9vy8dVbtiCDbkrNSkdlMYKs-CMaSmswUJbWlvHWQmSUsYqajDUpcDW1oxKYI5qR2pqKzZD98fcXei_0t9BtT4aaBrdQT9GRXHqwBeyoklKjlIT-hgDOLULvtVhrwhWB05qqxIndeCkMFeJU_LcneLHugX75_gFkwQPRwGkkt8egorGQ2fA-gBmULb3_8T_AH0WeAA</recordid><startdate>20180515</startdate><enddate>20180515</enddate><creator>Smullen, Shaun</creator><creator>McLaughlin, Noel P.</creator><creator>Evans, Paul</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></search><sort><creationdate>20180515</creationdate><title>Chemical synthesis of febrifugine and analogues</title><author>Smullen, Shaun ; McLaughlin, Noel P. ; Evans, Paul</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-f7a17fe7cd6c5433a96dc06ad2bdf437e9223382c0eb760ddb329e3f2af1b2d83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>3-hydroxypiperidine</topic><topic>Animals</topic><topic>Anti-angiogenic</topic><topic>Anti-fibrotic</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemistry</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</topic><topic>Anti-protozoal</topic><topic>Antimalarials - chemical synthesis</topic><topic>Antimalarials - chemistry</topic><topic>Antimalarials - pharmacology</topic><topic>Cyclization</topic><topic>Cycloaddition Reaction</topic><topic>Dichroine A and B</topic><topic>Febrifugine</topic><topic>Halofuginone</topic><topic>Humans</topic><topic>Isofebrifugine</topic><topic>Isomerization</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - chemistry</topic><topic>Piperidines - pharmacology</topic><topic>Plasmodium falciparum - drug effects</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - chemistry</topic><topic>Quinazolines - pharmacology</topic><topic>Quinazolinone</topic><topic>Quinazolinones - chemical synthesis</topic><topic>Quinazolinones - chemistry</topic><topic>Quinazolinones - pharmacology</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Smullen, Shaun</creatorcontrib><creatorcontrib>McLaughlin, Noel P.</creatorcontrib><creatorcontrib>Evans, Paul</creatorcontrib><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>Smullen, Shaun</au><au>McLaughlin, Noel P.</au><au>Evans, Paul</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical synthesis of febrifugine and analogues</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2018-05-15</date><risdate>2018</risdate><volume>26</volume><issue>9</issue><spage>2199</spage><epage>2220</epage><pages>2199-2220</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted]
The quinazolinone-containing 2,3-disubstituted piperidines febrifugine and isofebrifugine have been the subject of significant research efforts since their occurrence in Dichroa febrifuga and their anti-malarial actions were first described in the late 1940s. Subsequently they have also been shown to be present in other plants belonging to the hydrangea family and various analogues of febrifugine have been prepared in attempts to tune biological properties. The most notable analogue is termed halofuginone and a substantial body of work now demonstrates that this compound possesses potent human disease relevant activities. This review focuses on the literature associated with efforts dedicated towards uncovering the structures of febrifugine and isofebrifugine, the development of practical methods for their synthesis and the syntheses of structural analogues.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>29681487</pmid><doi>10.1016/j.bmc.2018.04.027</doi><tpages>22</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2018-05, Vol.26 (9), p.2199-2220 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | 3-hydroxypiperidine Animals Anti-angiogenic Anti-fibrotic Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis Anti-Inflammatory Agents, Non-Steroidal - chemistry Anti-Inflammatory Agents, Non-Steroidal - pharmacology Anti-protozoal Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Cyclization Cycloaddition Reaction Dichroine A and B Febrifugine Halofuginone Humans Isofebrifugine Isomerization Piperidines - chemical synthesis Piperidines - chemistry Piperidines - pharmacology Plasmodium falciparum - drug effects Quinazolines - chemical synthesis Quinazolines - chemistry Quinazolines - pharmacology Quinazolinone Quinazolinones - chemical synthesis Quinazolinones - chemistry Quinazolinones - pharmacology Stereoisomerism |
| title | Chemical synthesis of febrifugine and analogues |
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