Synthesis of 4-aminotetrahydropyran scaffolds for drug discovery
[Display omitted] Functionalised tetrahydropyran scaffolds were prepared using a tethered enol-ether Prins cyclisation and elaborated to show their potential use in library synthesis. The key 4-hydroxytetrahydropyran scaffold could be readily manipulated to the 4-azidotetrahydropyran that could be e...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2017-04, Vol.25 (7), p.2218-2225 |
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| container_issue | 7 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Nortcliffe, Andrew Milne, Gavin D.S. Hamza, Daniel Moody, Christopher J. |
| description | [Display omitted]
Functionalised tetrahydropyran scaffolds were prepared using a tethered enol-ether Prins cyclisation and elaborated to show their potential use in library synthesis. The key 4-hydroxytetrahydropyran scaffold could be readily manipulated to the 4-azidotetrahydropyran that could be elaborated via copper catalysed azide-alkyne cycloaddition or by reduction to the amine, to provide sp3-rich scaffolds useful for drug discovery. |
| doi_str_mv | 10.1016/j.bmc.2017.02.039 |
| format | Article |
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Functionalised tetrahydropyran scaffolds were prepared using a tethered enol-ether Prins cyclisation and elaborated to show their potential use in library synthesis. The key 4-hydroxytetrahydropyran scaffold could be readily manipulated to the 4-azidotetrahydropyran that could be elaborated via copper catalysed azide-alkyne cycloaddition or by reduction to the amine, to provide sp3-rich scaffolds useful for drug discovery.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2017.02.039</identifier><identifier>PMID: 28279558</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Amine functionalisation ; Azide-alkyne cycloaddition ; Cyclization ; Drug Discovery ; Furans - chemical synthesis ; Furans - chemistry ; Prins cyclisation ; Tetrahydropyran</subject><ispartof>Bioorganic & medicinal chemistry, 2017-04, Vol.25 (7), p.2218-2225</ispartof><rights>2017 Elsevier Ltd</rights><rights>Copyright © 2017 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c353t-d5d11c20a8b3606d7e4744bca0cb057f85e1b183604a623ba38af5185cec8aea3</citedby><cites>FETCH-LOGICAL-c353t-d5d11c20a8b3606d7e4744bca0cb057f85e1b183604a623ba38af5185cec8aea3</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.2017.02.039$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28279558$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nortcliffe, Andrew</creatorcontrib><creatorcontrib>Milne, Gavin D.S.</creatorcontrib><creatorcontrib>Hamza, Daniel</creatorcontrib><creatorcontrib>Moody, Christopher J.</creatorcontrib><title>Synthesis of 4-aminotetrahydropyran scaffolds for drug discovery</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted]
Functionalised tetrahydropyran scaffolds were prepared using a tethered enol-ether Prins cyclisation and elaborated to show their potential use in library synthesis. The key 4-hydroxytetrahydropyran scaffold could be readily manipulated to the 4-azidotetrahydropyran that could be elaborated via copper catalysed azide-alkyne cycloaddition or by reduction to the amine, to provide sp3-rich scaffolds useful for drug discovery.</description><subject>Amine functionalisation</subject><subject>Azide-alkyne cycloaddition</subject><subject>Cyclization</subject><subject>Drug Discovery</subject><subject>Furans - chemical synthesis</subject><subject>Furans - chemistry</subject><subject>Prins cyclisation</subject><subject>Tetrahydropyran</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kD1PwzAQhi0EglL4ASwoI0uCv-I4YgFVfEmVGIDZcuwLdZXExU4q5d-TqoWR6YZ73ld3D0JXBGcEE3G7zqrWZBSTIsM0w6w8QjPCBU8ZK8kxmuFSyBTLUpyh8xjXGGPKS3KKzqikRZnncobu38euX0F0MfF1wlPdus730Ae9Gm3wmzHoLolG17VvbExqHxIbhq_Eumj8FsJ4gU5q3US4PMw5-nx6_Fi8pMu359fFwzI1LGd9anNLiKFYy4oJLGwBvOC8MhqbCudFLXMgFZHTjmtBWaWZ1HVOZG7ASA2azdHNvncT_PcAsVftdAI0je7AD1ERWQheCibIhJI9aoKPMUCtNsG1OoyKYLUTp9ZqEqd24hSmahI3Za4P9UPVgv1L_JqagLs9ANOTWwdBReOgM2BdANMr690_9T9oVH59</recordid><startdate>20170401</startdate><enddate>20170401</enddate><creator>Nortcliffe, Andrew</creator><creator>Milne, Gavin D.S.</creator><creator>Hamza, Daniel</creator><creator>Moody, Christopher J.</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>20170401</creationdate><title>Synthesis of 4-aminotetrahydropyran scaffolds for drug discovery</title><author>Nortcliffe, Andrew ; Milne, Gavin D.S. ; Hamza, Daniel ; Moody, Christopher J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-d5d11c20a8b3606d7e4744bca0cb057f85e1b183604a623ba38af5185cec8aea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Amine functionalisation</topic><topic>Azide-alkyne cycloaddition</topic><topic>Cyclization</topic><topic>Drug Discovery</topic><topic>Furans - chemical synthesis</topic><topic>Furans - chemistry</topic><topic>Prins cyclisation</topic><topic>Tetrahydropyran</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nortcliffe, Andrew</creatorcontrib><creatorcontrib>Milne, Gavin D.S.</creatorcontrib><creatorcontrib>Hamza, Daniel</creatorcontrib><creatorcontrib>Moody, Christopher J.</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>Nortcliffe, Andrew</au><au>Milne, Gavin D.S.</au><au>Hamza, Daniel</au><au>Moody, Christopher J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 4-aminotetrahydropyran scaffolds for drug discovery</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2017-04-01</date><risdate>2017</risdate><volume>25</volume><issue>7</issue><spage>2218</spage><epage>2225</epage><pages>2218-2225</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted]
Functionalised tetrahydropyran scaffolds were prepared using a tethered enol-ether Prins cyclisation and elaborated to show their potential use in library synthesis. The key 4-hydroxytetrahydropyran scaffold could be readily manipulated to the 4-azidotetrahydropyran that could be elaborated via copper catalysed azide-alkyne cycloaddition or by reduction to the amine, to provide sp3-rich scaffolds useful for drug discovery.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>28279558</pmid><doi>10.1016/j.bmc.2017.02.039</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Bioorganic & medicinal chemistry, 2017-04, Vol.25 (7), p.2218-2225 |
| issn | 0968-0896 1464-3391 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Amine functionalisation Azide-alkyne cycloaddition Cyclization Drug Discovery Furans - chemical synthesis Furans - chemistry Prins cyclisation Tetrahydropyran |
| title | Synthesis of 4-aminotetrahydropyran scaffolds for drug discovery |
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