Loading…
Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones
A practical method for radiofluorination of anilines with [18F]fluoride via N‐arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F‐labeling to prepare [18F]fluoroarenes. The value of this methodology is further highlighted b...
Saved in:
| Published in: | Angewandte Chemie International Edition 2017-10, Vol.56 (42), p.13006-13010 |
|---|---|
| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c4834-5660049d0a972be3128397ed29229639cd1ab4f2553fc9e5dc6130637fdaef453 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c4834-5660049d0a972be3128397ed29229639cd1ab4f2553fc9e5dc6130637fdaef453 |
| container_end_page | 13010 |
| container_issue | 42 |
| container_start_page | 13006 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 56 |
| creator | Narayanam, Maruthi Kumar Ma, Gaoyuan Champagne, Pier Alexandre Houk, Kendall N. Murphy, Jennifer M. |
| description | A practical method for radiofluorination of anilines with [18F]fluoride via N‐arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F‐labeling to prepare [18F]fluoroarenes. The value of this methodology is further highlighted by successful application to prepare an 18F‐labeled neuropeptide.
Easy to handle: A practical radiofluorination of anilines with [18F]fluoride is achieved via N‐arylsydnone intermediates. This method displays broad functional group tolerance, is compatible to automation on a commercial radiosynthesis module and can facilitate rapid 18F‐labeling of peptides. |
| doi_str_mv | 10.1002/anie.201707274 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1946144723</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1946144723</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4834-5660049d0a972be3128397ed29229639cd1ab4f2553fc9e5dc6130637fdaef453</originalsourceid><addsrcrecordid>eNqFkE9LwzAYxoMobk6vHqXguTN_m-Y4xqaDMUHnSSSkbcoyumYmK9KbH8HP6CcxZXMePT3v4ff8XngAuEZwiCDEd6o2eogh4pBjTk9AHzGMYsI5OQ03JSTmKUM9cOH9OvBpCpNz0AtJKExYHyyf23q30t74yJbRK0qnb9Oqsc4qp2vto6yNFk1eabtdmcrk0ZMqjC07wtRqZ2zd1Rbfn18j11a-LWobWpfgrFSV11eHHICX6WQ5fojnj_ez8Wge5zT8j1mSQEhFAZXgONME4ZQIrgssMBYJEXmBVEZLzBgpc6FZkSeIwITwslC6pIwMwO3eu3X2vdF-J9e2cXV4KZGgCaKUYxKo4Z7KnfXe6VJundko10oEZTei7EaUxxFD4eagbbKNLo7472oBEHvgw1S6_UcnR4vZ5E_-AxOHfrQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1946144723</pqid></control><display><type>article</type><title>Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones</title><source>Wiley:Jisc Collections:Wiley Read and Publish Open Access 2024-2025 (reading list)</source><creator>Narayanam, Maruthi Kumar ; Ma, Gaoyuan ; Champagne, Pier Alexandre ; Houk, Kendall N. ; Murphy, Jennifer M.</creator><creatorcontrib>Narayanam, Maruthi Kumar ; Ma, Gaoyuan ; Champagne, Pier Alexandre ; Houk, Kendall N. ; Murphy, Jennifer M.</creatorcontrib><description>A practical method for radiofluorination of anilines with [18F]fluoride via N‐arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F‐labeling to prepare [18F]fluoroarenes. The value of this methodology is further highlighted by successful application to prepare an 18F‐labeled neuropeptide.
Easy to handle: A practical radiofluorination of anilines with [18F]fluoride is achieved via N‐arylsydnone intermediates. This method displays broad functional group tolerance, is compatible to automation on a commercial radiosynthesis module and can facilitate rapid 18F‐labeling of peptides.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201707274</identifier><identifier>PMID: 28834065</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aniline ; click chemistry ; Fluoridation ; Fluorides ; Fluorine Radioisotopes - chemistry ; fluorine-18 ; fluoroarene ; Intermediates ; Isotope Labeling ; Molecular Conformation ; Neuropeptides - chemistry ; peptide radiolabeling ; Positron-Emission Tomography ; Radiopharmaceuticals - chemical synthesis ; sydnone ; Sydnones - chemistry ; Thermodynamics</subject><ispartof>Angewandte Chemie International Edition, 2017-10, Vol.56 (42), p.13006-13010</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4834-5660049d0a972be3128397ed29229639cd1ab4f2553fc9e5dc6130637fdaef453</citedby><cites>FETCH-LOGICAL-c4834-5660049d0a972be3128397ed29229639cd1ab4f2553fc9e5dc6130637fdaef453</cites><orcidid>0000-0002-8492-4918</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28834065$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Narayanam, Maruthi Kumar</creatorcontrib><creatorcontrib>Ma, Gaoyuan</creatorcontrib><creatorcontrib>Champagne, Pier Alexandre</creatorcontrib><creatorcontrib>Houk, Kendall N.</creatorcontrib><creatorcontrib>Murphy, Jennifer M.</creatorcontrib><title>Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>A practical method for radiofluorination of anilines with [18F]fluoride via N‐arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F‐labeling to prepare [18F]fluoroarenes. The value of this methodology is further highlighted by successful application to prepare an 18F‐labeled neuropeptide.
Easy to handle: A practical radiofluorination of anilines with [18F]fluoride is achieved via N‐arylsydnone intermediates. This method displays broad functional group tolerance, is compatible to automation on a commercial radiosynthesis module and can facilitate rapid 18F‐labeling of peptides.</description><subject>Aniline</subject><subject>click chemistry</subject><subject>Fluoridation</subject><subject>Fluorides</subject><subject>Fluorine Radioisotopes - chemistry</subject><subject>fluorine-18</subject><subject>fluoroarene</subject><subject>Intermediates</subject><subject>Isotope Labeling</subject><subject>Molecular Conformation</subject><subject>Neuropeptides - chemistry</subject><subject>peptide radiolabeling</subject><subject>Positron-Emission Tomography</subject><subject>Radiopharmaceuticals - chemical synthesis</subject><subject>sydnone</subject><subject>Sydnones - chemistry</subject><subject>Thermodynamics</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkE9LwzAYxoMobk6vHqXguTN_m-Y4xqaDMUHnSSSkbcoyumYmK9KbH8HP6CcxZXMePT3v4ff8XngAuEZwiCDEd6o2eogh4pBjTk9AHzGMYsI5OQ03JSTmKUM9cOH9OvBpCpNz0AtJKExYHyyf23q30t74yJbRK0qnb9Oqsc4qp2vto6yNFk1eabtdmcrk0ZMqjC07wtRqZ2zd1Rbfn18j11a-LWobWpfgrFSV11eHHICX6WQ5fojnj_ez8Wge5zT8j1mSQEhFAZXgONME4ZQIrgssMBYJEXmBVEZLzBgpc6FZkSeIwITwslC6pIwMwO3eu3X2vdF-J9e2cXV4KZGgCaKUYxKo4Z7KnfXe6VJundko10oEZTei7EaUxxFD4eagbbKNLo7472oBEHvgw1S6_UcnR4vZ5E_-AxOHfrQ</recordid><startdate>20171009</startdate><enddate>20171009</enddate><creator>Narayanam, Maruthi Kumar</creator><creator>Ma, Gaoyuan</creator><creator>Champagne, Pier Alexandre</creator><creator>Houk, Kendall N.</creator><creator>Murphy, Jennifer M.</creator><general>Wiley Subscription Services, Inc</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>7TM</scope><scope>K9.</scope><orcidid>https://orcid.org/0000-0002-8492-4918</orcidid></search><sort><creationdate>20171009</creationdate><title>Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones</title><author>Narayanam, Maruthi Kumar ; Ma, Gaoyuan ; Champagne, Pier Alexandre ; Houk, Kendall N. ; Murphy, Jennifer M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4834-5660049d0a972be3128397ed29229639cd1ab4f2553fc9e5dc6130637fdaef453</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Aniline</topic><topic>click chemistry</topic><topic>Fluoridation</topic><topic>Fluorides</topic><topic>Fluorine Radioisotopes - chemistry</topic><topic>fluorine-18</topic><topic>fluoroarene</topic><topic>Intermediates</topic><topic>Isotope Labeling</topic><topic>Molecular Conformation</topic><topic>Neuropeptides - chemistry</topic><topic>peptide radiolabeling</topic><topic>Positron-Emission Tomography</topic><topic>Radiopharmaceuticals - chemical synthesis</topic><topic>sydnone</topic><topic>Sydnones - chemistry</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Narayanam, Maruthi Kumar</creatorcontrib><creatorcontrib>Ma, Gaoyuan</creatorcontrib><creatorcontrib>Champagne, Pier Alexandre</creatorcontrib><creatorcontrib>Houk, Kendall N.</creatorcontrib><creatorcontrib>Murphy, Jennifer M.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Narayanam, Maruthi Kumar</au><au>Ma, Gaoyuan</au><au>Champagne, Pier Alexandre</au><au>Houk, Kendall N.</au><au>Murphy, Jennifer M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-10-09</date><risdate>2017</risdate><volume>56</volume><issue>42</issue><spage>13006</spage><epage>13010</epage><pages>13006-13010</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A practical method for radiofluorination of anilines with [18F]fluoride via N‐arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F‐labeling to prepare [18F]fluoroarenes. The value of this methodology is further highlighted by successful application to prepare an 18F‐labeled neuropeptide.
Easy to handle: A practical radiofluorination of anilines with [18F]fluoride is achieved via N‐arylsydnone intermediates. This method displays broad functional group tolerance, is compatible to automation on a commercial radiosynthesis module and can facilitate rapid 18F‐labeling of peptides.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28834065</pmid><doi>10.1002/anie.201707274</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-8492-4918</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2017-10, Vol.56 (42), p.13006-13010 |
| issn | 1433-7851 1521-3773 |
| language | eng |
| recordid | cdi_proquest_journals_1946144723 |
| source | Wiley:Jisc Collections:Wiley Read and Publish Open Access 2024-2025 (reading list) |
| subjects | Aniline click chemistry Fluoridation Fluorides Fluorine Radioisotopes - chemistry fluorine-18 fluoroarene Intermediates Isotope Labeling Molecular Conformation Neuropeptides - chemistry peptide radiolabeling Positron-Emission Tomography Radiopharmaceuticals - chemical synthesis sydnone Sydnones - chemistry Thermodynamics |
| title | Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N‐Arylsydnones |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T02%3A13%3A24IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20%5B18F%5DFluoroarenes%20by%20Nucleophilic%20Radiofluorination%20of%20N%E2%80%90Arylsydnones&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Narayanam,%20Maruthi%20Kumar&rft.date=2017-10-09&rft.volume=56&rft.issue=42&rft.spage=13006&rft.epage=13010&rft.pages=13006-13010&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.201707274&rft_dat=%3Cproquest_cross%3E1946144723%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c4834-5660049d0a972be3128397ed29229639cd1ab4f2553fc9e5dc6130637fdaef453%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1946144723&rft_id=info:pmid/28834065&rfr_iscdi=true |