Nickel-Catalyzed C(sp3)–Sb Coupling of Chlorostibines with Unactivated Alkyl Chlorides and In Vitro Anticancer Activity of Products

Nickel-Catalyzed C(sp3)–Sb Coupling of Chlorostibines with Unactivated Alkyl Chlorides and In Vitro Anticancer Activity of Products

In this study, we present a nickel-catalyzed reductive C­(sp3)–Sb coupling of unactivated alkyl chlorides with chlorostibines. This approach is highly versatile, tolerating various functional groups such as acetal, alkene, nitrile, amine, ester, silyl ether, thioether, and various heterocyclic compo...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2024-01, Vol.26 (1), p.344-349
Hauptverfasser: Le, Liyuan, Yin, Mingming, Zeng, Huifan, Xie, Wuxing, Zhou, Wenjun, Chen, Yi, Xiong, Biquan, Yin, Shuang-Feng, Kambe, Nobuaki, Qiu, Renhua
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 349
container_issue 1
container_start_page 344
container_title Organic letters
container_volume 26
creator Le, Liyuan
Yin, Mingming
Zeng, Huifan
Xie, Wuxing
Zhou, Wenjun
Chen, Yi
Xiong, Biquan
Yin, Shuang-Feng
Kambe, Nobuaki
Qiu, Renhua
description In this study, we present a nickel-catalyzed reductive C­(sp3)–Sb coupling of unactivated alkyl chlorides with chlorostibines. This approach is highly versatile, tolerating various functional groups such as acetal, alkene, nitrile, amine, ester, silyl ether, thioether, and various heterocyclic compounds. Notably, the late-stage modification of bioactive molecules and the satisfactory anticancer activity against cancerous MDA-MB-231 also demonstrate the potential application.
doi_str_mv 10.1021/acs.orglett.3c04008
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2906773262</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2906773262</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-310d15b6ee2a9c243f791c0d4da8a2f357d9de50aa4f4dd859e2038f603023553</originalsourceid><addsrcrecordid>eNp9kMtOGzEUhq2qiFt5gkqVl7CYcGyP57KMRhSQECC1dDtybA8YHDu1PUVhxYYn4A15EhwlZcnKR9b3_UfnR-g7gQkBSo6FjBMfbq1OacIklADNF7RLOGVFDZx-_Zgr2EF7Md4DkPzTbqMd1pCy5i3bRS-XRj5oW3QiCbt80gp3h3HBjt6eX3_NcOfHhTXuFvsBd3fWBx-TmRmnI3406Q7fOCGT-SdS9qb2YWnXlFEZEE7hc4f_mBQ8nrpkpHBSBzxdGSYtV5nXwatRpvgNbQ3CRn2weffRzc-T391ZcXF1et5NLwrBSp4KRkARPqu0pqKVtGRD3RIJqlSiEXRgvFat0hyEKIdSqYa3mgJrhgoYUMY520eH69xF8H9HHVM_N1Fqa4XTfow9baGqa0YrmlG2RmU-OgY99Itg5iIsewL9qv8-999v-u83_Wfrx2bBOJtr9eH8LzwDx2tgZd_7Mbh876eR74W4llc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2906773262</pqid></control><display><type>article</type><title>Nickel-Catalyzed C(sp3)–Sb Coupling of Chlorostibines with Unactivated Alkyl Chlorides and In Vitro Anticancer Activity of Products</title><source>ACS Publications</source><creator>Le, Liyuan ; Yin, Mingming ; Zeng, Huifan ; Xie, Wuxing ; Zhou, Wenjun ; Chen, Yi ; Xiong, Biquan ; Yin, Shuang-Feng ; Kambe, Nobuaki ; Qiu, Renhua</creator><creatorcontrib>Le, Liyuan ; Yin, Mingming ; Zeng, Huifan ; Xie, Wuxing ; Zhou, Wenjun ; Chen, Yi ; Xiong, Biquan ; Yin, Shuang-Feng ; Kambe, Nobuaki ; Qiu, Renhua</creatorcontrib><description>In this study, we present a nickel-catalyzed reductive C­(sp3)–Sb coupling of unactivated alkyl chlorides with chlorostibines. This approach is highly versatile, tolerating various functional groups such as acetal, alkene, nitrile, amine, ester, silyl ether, thioether, and various heterocyclic compounds. Notably, the late-stage modification of bioactive molecules and the satisfactory anticancer activity against cancerous MDA-MB-231 also demonstrate the potential application.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.3c04008</identifier><identifier>PMID: 38147593</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2024-01, Vol.26 (1), p.344-349</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-310d15b6ee2a9c243f791c0d4da8a2f357d9de50aa4f4dd859e2038f603023553</citedby><cites>FETCH-LOGICAL-a345t-310d15b6ee2a9c243f791c0d4da8a2f357d9de50aa4f4dd859e2038f603023553</cites><orcidid>0000-0002-6490-6384 ; 0000-0002-8423-9988 ; 0000-0001-9857-9804</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.3c04008$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.3c04008$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38147593$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Le, Liyuan</creatorcontrib><creatorcontrib>Yin, Mingming</creatorcontrib><creatorcontrib>Zeng, Huifan</creatorcontrib><creatorcontrib>Xie, Wuxing</creatorcontrib><creatorcontrib>Zhou, Wenjun</creatorcontrib><creatorcontrib>Chen, Yi</creatorcontrib><creatorcontrib>Xiong, Biquan</creatorcontrib><creatorcontrib>Yin, Shuang-Feng</creatorcontrib><creatorcontrib>Kambe, Nobuaki</creatorcontrib><creatorcontrib>Qiu, Renhua</creatorcontrib><title>Nickel-Catalyzed C(sp3)–Sb Coupling of Chlorostibines with Unactivated Alkyl Chlorides and In Vitro Anticancer Activity of Products</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>In this study, we present a nickel-catalyzed reductive C­(sp3)–Sb coupling of unactivated alkyl chlorides with chlorostibines. This approach is highly versatile, tolerating various functional groups such as acetal, alkene, nitrile, amine, ester, silyl ether, thioether, and various heterocyclic compounds. Notably, the late-stage modification of bioactive molecules and the satisfactory anticancer activity against cancerous MDA-MB-231 also demonstrate the potential application.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kMtOGzEUhq2qiFt5gkqVl7CYcGyP57KMRhSQECC1dDtybA8YHDu1PUVhxYYn4A15EhwlZcnKR9b3_UfnR-g7gQkBSo6FjBMfbq1OacIklADNF7RLOGVFDZx-_Zgr2EF7Md4DkPzTbqMd1pCy5i3bRS-XRj5oW3QiCbt80gp3h3HBjt6eX3_NcOfHhTXuFvsBd3fWBx-TmRmnI3406Q7fOCGT-SdS9qb2YWnXlFEZEE7hc4f_mBQ8nrpkpHBSBzxdGSYtV5nXwatRpvgNbQ3CRn2weffRzc-T391ZcXF1et5NLwrBSp4KRkARPqu0pqKVtGRD3RIJqlSiEXRgvFat0hyEKIdSqYa3mgJrhgoYUMY520eH69xF8H9HHVM_N1Fqa4XTfow9baGqa0YrmlG2RmU-OgY99Itg5iIsewL9qv8-999v-u83_Wfrx2bBOJtr9eH8LzwDx2tgZd_7Mbh876eR74W4llc</recordid><startdate>20240112</startdate><enddate>20240112</enddate><creator>Le, Liyuan</creator><creator>Yin, Mingming</creator><creator>Zeng, Huifan</creator><creator>Xie, Wuxing</creator><creator>Zhou, Wenjun</creator><creator>Chen, Yi</creator><creator>Xiong, Biquan</creator><creator>Yin, Shuang-Feng</creator><creator>Kambe, Nobuaki</creator><creator>Qiu, Renhua</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6490-6384</orcidid><orcidid>https://orcid.org/0000-0002-8423-9988</orcidid><orcidid>https://orcid.org/0000-0001-9857-9804</orcidid></search><sort><creationdate>20240112</creationdate><title>Nickel-Catalyzed C(sp3)–Sb Coupling of Chlorostibines with Unactivated Alkyl Chlorides and In Vitro Anticancer Activity of Products</title><author>Le, Liyuan ; Yin, Mingming ; Zeng, Huifan ; Xie, Wuxing ; Zhou, Wenjun ; Chen, Yi ; Xiong, Biquan ; Yin, Shuang-Feng ; Kambe, Nobuaki ; Qiu, Renhua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-310d15b6ee2a9c243f791c0d4da8a2f357d9de50aa4f4dd859e2038f603023553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Le, Liyuan</creatorcontrib><creatorcontrib>Yin, Mingming</creatorcontrib><creatorcontrib>Zeng, Huifan</creatorcontrib><creatorcontrib>Xie, Wuxing</creatorcontrib><creatorcontrib>Zhou, Wenjun</creatorcontrib><creatorcontrib>Chen, Yi</creatorcontrib><creatorcontrib>Xiong, Biquan</creatorcontrib><creatorcontrib>Yin, Shuang-Feng</creatorcontrib><creatorcontrib>Kambe, Nobuaki</creatorcontrib><creatorcontrib>Qiu, Renhua</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Le, Liyuan</au><au>Yin, Mingming</au><au>Zeng, Huifan</au><au>Xie, Wuxing</au><au>Zhou, Wenjun</au><au>Chen, Yi</au><au>Xiong, Biquan</au><au>Yin, Shuang-Feng</au><au>Kambe, Nobuaki</au><au>Qiu, Renhua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nickel-Catalyzed C(sp3)–Sb Coupling of Chlorostibines with Unactivated Alkyl Chlorides and In Vitro Anticancer Activity of Products</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2024-01-12</date><risdate>2024</risdate><volume>26</volume><issue>1</issue><spage>344</spage><epage>349</epage><pages>344-349</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>In this study, we present a nickel-catalyzed reductive C­(sp3)–Sb coupling of unactivated alkyl chlorides with chlorostibines. This approach is highly versatile, tolerating various functional groups such as acetal, alkene, nitrile, amine, ester, silyl ether, thioether, and various heterocyclic compounds. Notably, the late-stage modification of bioactive molecules and the satisfactory anticancer activity against cancerous MDA-MB-231 also demonstrate the potential application.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>38147593</pmid><doi>10.1021/acs.orglett.3c04008</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-6490-6384</orcidid><orcidid>https://orcid.org/0000-0002-8423-9988</orcidid><orcidid>https://orcid.org/0000-0001-9857-9804</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2024-01, Vol.26 (1), p.344-349
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2906773262
source ACS Publications
title Nickel-Catalyzed C(sp3)–Sb Coupling of Chlorostibines with Unactivated Alkyl Chlorides and In Vitro Anticancer Activity of Products
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T14%3A48%3A33IST&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=Nickel-Catalyzed%20C(sp3)%E2%80%93Sb%20Coupling%20of%20Chlorostibines%20with%20Unactivated%20Alkyl%20Chlorides%20and%20In%20Vitro%20Anticancer%20Activity%20of%20Products&rft.jtitle=Organic%20letters&rft.au=Le,%20Liyuan&rft.date=2024-01-12&rft.volume=26&rft.issue=1&rft.spage=344&rft.epage=349&rft.pages=344-349&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.3c04008&rft_dat=%3Cproquest_cross%3E2906773262%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2906773262&rft_id=info:pmid/38147593&rfr_iscdi=true