Loading…

Development of an advanced synthetic route to macrosphelides and its application to the discovery of a more potent macrosphelide derivative

The discovery of a more cytotoxic macrosphelide derivative, including its total synthesis and bioassay are described. Application of the Koide protocol to a readily available propagylic alcohol allowed the rapid and practical synthesis of a macrosphelide A skeleton. This strategy enabled the success...

Full description

Saved in:
Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2014-09, Vol.19 (10), p.15572-15583
Main Authors: Heo, Yu Mi, Lee, Hunseok, Shin, Young Kee, Paek, Seung-Mann
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-c496t-870555fef2701bbda4f7417dbccf031c2afa06268a4c83a3d447e363dc905c3f3
cites cdi_FETCH-LOGICAL-c496t-870555fef2701bbda4f7417dbccf031c2afa06268a4c83a3d447e363dc905c3f3
container_end_page 15583
container_issue 10
container_start_page 15572
container_title Molecules (Basel, Switzerland)
container_volume 19
creator Heo, Yu Mi
Lee, Hunseok
Shin, Young Kee
Paek, Seung-Mann
description The discovery of a more cytotoxic macrosphelide derivative, including its total synthesis and bioassay are described. Application of the Koide protocol to a readily available propagylic alcohol allowed the rapid and practical synthesis of a macrosphelide A skeleton. This strategy enabled the successful improvement of the cytotoxic activity of the macrosphelide derivative.
doi_str_mv 10.3390/molecules191015572
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_616e624fbe344fa48da71a874b579b6f</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_616e624fbe344fa48da71a874b579b6f</doaj_id><sourcerecordid>3495038061</sourcerecordid><originalsourceid>FETCH-LOGICAL-c496t-870555fef2701bbda4f7417dbccf031c2afa06268a4c83a3d447e363dc905c3f3</originalsourceid><addsrcrecordid>eNplks1u3CAUha2oUZOmfYEsKqSuJwXzZ28qVWmbRoqUTbtGGC4ZRrZxAVuaZ8hLF2fSKKOuLoJzvnsPUFWXBF9R2uLPQ-jBzD0k0hJMOJf1SXVOWI03FLP2zav1WfUupR3GNWGEv63Oal6LRhJ-Xj1-gwX6MA0wZhQc0iPSdtGjAYvSfsxbyN6gGOYMKAc0aBNDmrbQewupqC3yudRp6r3R2YdxVRUXsj6ZsEDcP1HRECKgKeS1zREEWYh-KdYF3lenTvcJPjzXi-r3j--_rn9u7u5vbq-_3m0Ma0XeNBJzzh24WmLSdVYzJxmRtjPGYUpMrZ3GogTUzDRUU8uYBCqoNS3mhjp6Ud0euDbonZqiH3Tcq6C9etoI8UHpWGL3oAQRIGrmOqCMOc0aqyXRjWQdl20nVtaXA2uauwGsKfmi7o-gxyej36qHsChRphdSFsCnZ0AMf2ZIWe3CHMeSX5HSuSWtpG1R1QfVenMpgnvpQLBaP4P6_zMU08fXs71Y_r0-_Qv4T7b4</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1624919739</pqid></control><display><type>article</type><title>Development of an advanced synthetic route to macrosphelides and its application to the discovery of a more potent macrosphelide derivative</title><source>Publicly Available Content Database</source><source>PubMed Central(OpenAccess)</source><creator>Heo, Yu Mi ; Lee, Hunseok ; Shin, Young Kee ; Paek, Seung-Mann</creator><creatorcontrib>Heo, Yu Mi ; Lee, Hunseok ; Shin, Young Kee ; Paek, Seung-Mann</creatorcontrib><description>The discovery of a more cytotoxic macrosphelide derivative, including its total synthesis and bioassay are described. Application of the Koide protocol to a readily available propagylic alcohol allowed the rapid and practical synthesis of a macrosphelide A skeleton. This strategy enabled the successful improvement of the cytotoxic activity of the macrosphelide derivative.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules191015572</identifier><identifier>PMID: 25268715</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Acids ; Alcohol ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - toxicity ; Biological Products - chemistry ; Carbon ; Cell Line ; Cell Survival - drug effects ; Chemistry ; Chemistry Techniques, Synthetic ; Cytotoxicity ; Drug Discovery ; Heterocyclic Compounds - chemical synthesis ; Heterocyclic Compounds - chemistry ; Heterocyclic Compounds - toxicity ; Humans ; macrosphelides ; Molecular Structure ; natural product ; Natural products ; Oxidation ; Pharmacy ; total synthesis</subject><ispartof>Molecules (Basel, Switzerland), 2014-09, Vol.19 (10), p.15572-15583</ispartof><rights>Copyright MDPI AG 2014</rights><rights>2014 by the authors. 2014</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c496t-870555fef2701bbda4f7417dbccf031c2afa06268a4c83a3d447e363dc905c3f3</citedby><cites>FETCH-LOGICAL-c496t-870555fef2701bbda4f7417dbccf031c2afa06268a4c83a3d447e363dc905c3f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1624919739/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1624919739?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25268715$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Heo, Yu Mi</creatorcontrib><creatorcontrib>Lee, Hunseok</creatorcontrib><creatorcontrib>Shin, Young Kee</creatorcontrib><creatorcontrib>Paek, Seung-Mann</creatorcontrib><title>Development of an advanced synthetic route to macrosphelides and its application to the discovery of a more potent macrosphelide derivative</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>The discovery of a more cytotoxic macrosphelide derivative, including its total synthesis and bioassay are described. Application of the Koide protocol to a readily available propagylic alcohol allowed the rapid and practical synthesis of a macrosphelide A skeleton. This strategy enabled the successful improvement of the cytotoxic activity of the macrosphelide derivative.</description><subject>Acids</subject><subject>Alcohol</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - toxicity</subject><subject>Biological Products - chemistry</subject><subject>Carbon</subject><subject>Cell Line</subject><subject>Cell Survival - drug effects</subject><subject>Chemistry</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Cytotoxicity</subject><subject>Drug Discovery</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic Compounds - toxicity</subject><subject>Humans</subject><subject>macrosphelides</subject><subject>Molecular Structure</subject><subject>natural product</subject><subject>Natural products</subject><subject>Oxidation</subject><subject>Pharmacy</subject><subject>total synthesis</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplks1u3CAUha2oUZOmfYEsKqSuJwXzZ28qVWmbRoqUTbtGGC4ZRrZxAVuaZ8hLF2fSKKOuLoJzvnsPUFWXBF9R2uLPQ-jBzD0k0hJMOJf1SXVOWI03FLP2zav1WfUupR3GNWGEv63Oal6LRhJ-Xj1-gwX6MA0wZhQc0iPSdtGjAYvSfsxbyN6gGOYMKAc0aBNDmrbQewupqC3yudRp6r3R2YdxVRUXsj6ZsEDcP1HRECKgKeS1zREEWYh-KdYF3lenTvcJPjzXi-r3j--_rn9u7u5vbq-_3m0Ma0XeNBJzzh24WmLSdVYzJxmRtjPGYUpMrZ3GogTUzDRUU8uYBCqoNS3mhjp6Ud0euDbonZqiH3Tcq6C9etoI8UHpWGL3oAQRIGrmOqCMOc0aqyXRjWQdl20nVtaXA2uauwGsKfmi7o-gxyej36qHsChRphdSFsCnZ0AMf2ZIWe3CHMeSX5HSuSWtpG1R1QfVenMpgnvpQLBaP4P6_zMU08fXs71Y_r0-_Qv4T7b4</recordid><startdate>20140929</startdate><enddate>20140929</enddate><creator>Heo, Yu Mi</creator><creator>Lee, Hunseok</creator><creator>Shin, Young Kee</creator><creator>Paek, Seung-Mann</creator><general>MDPI AG</general><general>MDPI</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>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20140929</creationdate><title>Development of an advanced synthetic route to macrosphelides and its application to the discovery of a more potent macrosphelide derivative</title><author>Heo, Yu Mi ; Lee, Hunseok ; Shin, Young Kee ; Paek, Seung-Mann</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c496t-870555fef2701bbda4f7417dbccf031c2afa06268a4c83a3d447e363dc905c3f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Acids</topic><topic>Alcohol</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - toxicity</topic><topic>Biological Products - chemistry</topic><topic>Carbon</topic><topic>Cell Line</topic><topic>Cell Survival - drug effects</topic><topic>Chemistry</topic><topic>Chemistry Techniques, Synthetic</topic><topic>Cytotoxicity</topic><topic>Drug Discovery</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic Compounds - toxicity</topic><topic>Humans</topic><topic>macrosphelides</topic><topic>Molecular Structure</topic><topic>natural product</topic><topic>Natural products</topic><topic>Oxidation</topic><topic>Pharmacy</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Heo, Yu Mi</creatorcontrib><creatorcontrib>Lee, Hunseok</creatorcontrib><creatorcontrib>Shin, Young Kee</creatorcontrib><creatorcontrib>Paek, Seung-Mann</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health &amp; Medical Complete (ProQuest Database)</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health &amp; Medical Complete (Alumni)</collection><collection>Health &amp; Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Heo, Yu Mi</au><au>Lee, Hunseok</au><au>Shin, Young Kee</au><au>Paek, Seung-Mann</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Development of an advanced synthetic route to macrosphelides and its application to the discovery of a more potent macrosphelide derivative</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2014-09-29</date><risdate>2014</risdate><volume>19</volume><issue>10</issue><spage>15572</spage><epage>15583</epage><pages>15572-15583</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>The discovery of a more cytotoxic macrosphelide derivative, including its total synthesis and bioassay are described. Application of the Koide protocol to a readily available propagylic alcohol allowed the rapid and practical synthesis of a macrosphelide A skeleton. This strategy enabled the successful improvement of the cytotoxic activity of the macrosphelide derivative.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>25268715</pmid><doi>10.3390/molecules191015572</doi><tpages>12</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1420-3049
ispartof Molecules (Basel, Switzerland), 2014-09, Vol.19 (10), p.15572-15583
issn 1420-3049
1420-3049
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_616e624fbe344fa48da71a874b579b6f
source Publicly Available Content Database; PubMed Central(OpenAccess)
subjects Acids
Alcohol
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - toxicity
Biological Products - chemistry
Carbon
Cell Line
Cell Survival - drug effects
Chemistry
Chemistry Techniques, Synthetic
Cytotoxicity
Drug Discovery
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Heterocyclic Compounds - toxicity
Humans
macrosphelides
Molecular Structure
natural product
Natural products
Oxidation
Pharmacy
total synthesis
title Development of an advanced synthetic route to macrosphelides and its application to the discovery of a more potent macrosphelide derivative
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T17%3A41%3A22IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Development%20of%20an%20advanced%20synthetic%20route%20to%20macrosphelides%20and%20its%20application%20to%20the%20discovery%20of%20a%20more%20potent%20macrosphelide%20derivative&rft.jtitle=Molecules%20(Basel,%20Switzerland)&rft.au=Heo,%20Yu%20Mi&rft.date=2014-09-29&rft.volume=19&rft.issue=10&rft.spage=15572&rft.epage=15583&rft.pages=15572-15583&rft.issn=1420-3049&rft.eissn=1420-3049&rft_id=info:doi/10.3390/molecules191015572&rft_dat=%3Cproquest_doaj_%3E3495038061%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c496t-870555fef2701bbda4f7417dbccf031c2afa06268a4c83a3d447e363dc905c3f3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1624919739&rft_id=info:pmid/25268715&rfr_iscdi=true