Concise Three Step Synthesis of the Bioactive Alkaloid Huajiaosimuline via a Zn(OTf)2 -Promoted Meinwald Rearrangement

Concise Three Step Synthesis of the Bioactive Alkaloid Huajiaosimuline via a Zn(OTf)2 -Promoted Meinwald Rearrangement

The synthesis of the biologically active alkaloid huajiaosimulne, isolated from the roots of Zanthoxylum simulans, is reported. The natural product was assembled from simple commercial reagents via initial domino Knoevenagel/oxa-6π-electrocyclization followed by epoxidation and an epoxide/ketone rea...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemistry & biodiversity 2024-12, p.e202402680
Hauptverfasser: Adessi, Tonino, Centurión, Enzo, De La Horra, Camila, Chocan, Camila, Bajicoff, Sofía, Blank, Viviana, Roguin, Leonor, Riveira, Martín J
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page
container_issue
container_start_page e202402680
container_title Chemistry & biodiversity
container_volume
creator Adessi, Tonino
Centurión, Enzo
De La Horra, Camila
Chocan, Camila
Bajicoff, Sofía
Blank, Viviana
Roguin, Leonor
Riveira, Martín J
description The synthesis of the biologically active alkaloid huajiaosimulne, isolated from the roots of Zanthoxylum simulans, is reported. The natural product was assembled from simple commercial reagents via initial domino Knoevenagel/oxa-6π-electrocyclization followed by epoxidation and an epoxide/ketone rearrangement promoted by Zn(OTf)2. In vitro cytotoxicity assays identified natural products huajiaosimuline and simulansine as moderate antiproliferative agents against murine colon cancer CT26 cells.
doi_str_mv 10.1002/cbdv.202402680
format Article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_3140920549</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3140920549</sourcerecordid><originalsourceid>FETCH-LOGICAL-p960-a030fbb282628c1d46046eb5654449555844625014659af0d8174c4b1c6551063</originalsourceid><addsrcrecordid>eNpNkD1PwzAURS0EoqWwMiKPZUh5dmzjjKXiSyoqoplYIid5oS5JXOIkqP-eSBSJ6Z7h6AyXkEsGMwbAb7I072ccuACuNByRMVOMB0xrOP7HI3Lm_XbwB9anZBRGikME4Zj0C1dn1iONNw0iXbe4o-t93W7QW09dQQeid9aZrLU90nn5aUpnc_rUma01ztuqK22NtLeGGvpeT1dxcc1p8Nq4yrWY0xe09bcpc_qGpmlM_YEV1u05OSlM6fHisBMSP9zHi6dguXp8XsyXwS5SEBgIoUhTrrniOmO5UCAUplJJIUQkpdRCKC6BCSUjU0Cu2a3IRMoyJSUDFU7I9De7a9xXh75NKuszLEtTo-t8EjIBEQcpokG9OqhdWmGe7BpbmWaf_F0V_gBJPml2</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3140920549</pqid></control><display><type>article</type><title>Concise Three Step Synthesis of the Bioactive Alkaloid Huajiaosimuline via a Zn(OTf)2 -Promoted Meinwald Rearrangement</title><source>Access via Wiley Online Library</source><creator>Adessi, Tonino ; Centurión, Enzo ; De La Horra, Camila ; Chocan, Camila ; Bajicoff, Sofía ; Blank, Viviana ; Roguin, Leonor ; Riveira, Martín J</creator><creatorcontrib>Adessi, Tonino ; Centurión, Enzo ; De La Horra, Camila ; Chocan, Camila ; Bajicoff, Sofía ; Blank, Viviana ; Roguin, Leonor ; Riveira, Martín J</creatorcontrib><description>The synthesis of the biologically active alkaloid huajiaosimulne, isolated from the roots of Zanthoxylum simulans, is reported. The natural product was assembled from simple commercial reagents via initial domino Knoevenagel/oxa-6π-electrocyclization followed by epoxidation and an epoxide/ketone rearrangement promoted by Zn(OTf)2. In vitro cytotoxicity assays identified natural products huajiaosimuline and simulansine as moderate antiproliferative agents against murine colon cancer CT26 cells.</description><identifier>ISSN: 1612-1880</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.202402680</identifier><identifier>PMID: 39620903</identifier><language>eng</language><publisher>Switzerland</publisher><ispartof>Chemistry &amp; biodiversity, 2024-12, p.e202402680</ispartof><rights>2024 Wiley‐VCH GmbH.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></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/39620903$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Adessi, Tonino</creatorcontrib><creatorcontrib>Centurión, Enzo</creatorcontrib><creatorcontrib>De La Horra, Camila</creatorcontrib><creatorcontrib>Chocan, Camila</creatorcontrib><creatorcontrib>Bajicoff, Sofía</creatorcontrib><creatorcontrib>Blank, Viviana</creatorcontrib><creatorcontrib>Roguin, Leonor</creatorcontrib><creatorcontrib>Riveira, Martín J</creatorcontrib><title>Concise Three Step Synthesis of the Bioactive Alkaloid Huajiaosimuline via a Zn(OTf)2 -Promoted Meinwald Rearrangement</title><title>Chemistry &amp; biodiversity</title><addtitle>Chem Biodivers</addtitle><description>The synthesis of the biologically active alkaloid huajiaosimulne, isolated from the roots of Zanthoxylum simulans, is reported. The natural product was assembled from simple commercial reagents via initial domino Knoevenagel/oxa-6π-electrocyclization followed by epoxidation and an epoxide/ketone rearrangement promoted by Zn(OTf)2. In vitro cytotoxicity assays identified natural products huajiaosimuline and simulansine as moderate antiproliferative agents against murine colon cancer CT26 cells.</description><issn>1612-1880</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpNkD1PwzAURS0EoqWwMiKPZUh5dmzjjKXiSyoqoplYIid5oS5JXOIkqP-eSBSJ6Z7h6AyXkEsGMwbAb7I072ccuACuNByRMVOMB0xrOP7HI3Lm_XbwB9anZBRGikME4Zj0C1dn1iONNw0iXbe4o-t93W7QW09dQQeid9aZrLU90nn5aUpnc_rUma01ztuqK22NtLeGGvpeT1dxcc1p8Nq4yrWY0xe09bcpc_qGpmlM_YEV1u05OSlM6fHisBMSP9zHi6dguXp8XsyXwS5SEBgIoUhTrrniOmO5UCAUplJJIUQkpdRCKC6BCSUjU0Cu2a3IRMoyJSUDFU7I9De7a9xXh75NKuszLEtTo-t8EjIBEQcpokG9OqhdWmGe7BpbmWaf_F0V_gBJPml2</recordid><startdate>20241202</startdate><enddate>20241202</enddate><creator>Adessi, Tonino</creator><creator>Centurión, Enzo</creator><creator>De La Horra, Camila</creator><creator>Chocan, Camila</creator><creator>Bajicoff, Sofía</creator><creator>Blank, Viviana</creator><creator>Roguin, Leonor</creator><creator>Riveira, Martín J</creator><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20241202</creationdate><title>Concise Three Step Synthesis of the Bioactive Alkaloid Huajiaosimuline via a Zn(OTf)2 -Promoted Meinwald Rearrangement</title><author>Adessi, Tonino ; Centurión, Enzo ; De La Horra, Camila ; Chocan, Camila ; Bajicoff, Sofía ; Blank, Viviana ; Roguin, Leonor ; Riveira, Martín J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p960-a030fbb282628c1d46046eb5654449555844625014659af0d8174c4b1c6551063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Adessi, Tonino</creatorcontrib><creatorcontrib>Centurión, Enzo</creatorcontrib><creatorcontrib>De La Horra, Camila</creatorcontrib><creatorcontrib>Chocan, Camila</creatorcontrib><creatorcontrib>Bajicoff, Sofía</creatorcontrib><creatorcontrib>Blank, Viviana</creatorcontrib><creatorcontrib>Roguin, Leonor</creatorcontrib><creatorcontrib>Riveira, Martín J</creatorcontrib><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry &amp; biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Adessi, Tonino</au><au>Centurión, Enzo</au><au>De La Horra, Camila</au><au>Chocan, Camila</au><au>Bajicoff, Sofía</au><au>Blank, Viviana</au><au>Roguin, Leonor</au><au>Riveira, Martín J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Concise Three Step Synthesis of the Bioactive Alkaloid Huajiaosimuline via a Zn(OTf)2 -Promoted Meinwald Rearrangement</atitle><jtitle>Chemistry &amp; biodiversity</jtitle><addtitle>Chem Biodivers</addtitle><date>2024-12-02</date><risdate>2024</risdate><spage>e202402680</spage><pages>e202402680-</pages><issn>1612-1880</issn><eissn>1612-1880</eissn><abstract>The synthesis of the biologically active alkaloid huajiaosimulne, isolated from the roots of Zanthoxylum simulans, is reported. The natural product was assembled from simple commercial reagents via initial domino Knoevenagel/oxa-6π-electrocyclization followed by epoxidation and an epoxide/ketone rearrangement promoted by Zn(OTf)2. In vitro cytotoxicity assays identified natural products huajiaosimuline and simulansine as moderate antiproliferative agents against murine colon cancer CT26 cells.</abstract><cop>Switzerland</cop><pmid>39620903</pmid><doi>10.1002/cbdv.202402680</doi><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1612-1880
ispartof Chemistry & biodiversity, 2024-12, p.e202402680
issn 1612-1880
1612-1880
language eng
recordid cdi_proquest_miscellaneous_3140920549
source Access via Wiley Online Library
title Concise Three Step Synthesis of the Bioactive Alkaloid Huajiaosimuline via a Zn(OTf)2 -Promoted Meinwald Rearrangement
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T19%3A58%3A52IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Concise%20Three%20Step%20Synthesis%20of%20the%20Bioactive%20Alkaloid%20Huajiaosimuline%20via%20a%20Zn(OTf)2%20-Promoted%20Meinwald%20Rearrangement&rft.jtitle=Chemistry%20&%20biodiversity&rft.au=Adessi,%20Tonino&rft.date=2024-12-02&rft.spage=e202402680&rft.pages=e202402680-&rft.issn=1612-1880&rft.eissn=1612-1880&rft_id=info:doi/10.1002/cbdv.202402680&rft_dat=%3Cproquest_pubme%3E3140920549%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3140920549&rft_id=info:pmid/39620903&rfr_iscdi=true