Natural tetraponerines: a general synthesis and antiproliferative activity.
Identifieur interne : 000105 ( Main/Exploration ); précédent : 000104; suivant : 000106Natural tetraponerines: a general synthesis and antiproliferative activity.
Auteurs : RBID : pubmed:24731136Abstract
A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert-butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5-6-5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6-6-5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotoxic activity of (+)-T7 against breast carcinoma cell line MCF-7.
DOI: 10.1021/jo500446f
PubMed: 24731136
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Natural tetraponerines: a general synthesis and antiproliferative activity.</title><author><name sortKey="Bosque, Irene" uniqKey="Bosque I">Irene Bosque</name><affiliation wicri:level="1"><nlm:affiliation>Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante</wicri:regionArea></affiliation></author><author><name sortKey="Gonzalez Gomez, Jose C" uniqKey="Gonzalez Gomez J">Jose C Gonzalez-Gomez</name></author><author><name sortKey="Loza, Mar A Isabel" uniqKey="Loza M">María Isabel Loza</name></author><author><name sortKey="Brea, Jose" uniqKey="Brea J">José Brea</name></author></titleStmt><publicationStmt><date when="2014">2014</date><idno type="doi">10.1021/jo500446f</idno><idno type="RBID">pubmed:24731136</idno><idno type="pmid">24731136</idno><idno type="wicri:Area/Main/Corpus">000065</idno><idno type="wicri:Area/Main/Curation">000065</idno><idno type="wicri:Area/Main/Exploration">000105</idno></publicationStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert-butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5-6-5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6-6-5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotoxic activity of (+)-T7 against breast carcinoma cell line MCF-7.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="In-Data-Review"><PMID Version="1">24731136</PMID><DateCreated><Year>2014</Year><Month>05</Month><Day>05</Day></DateCreated><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><Volume>79</Volume><Issue>9</Issue><PubDate><Year>2014</Year><Month>May</Month><Day>2</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Natural tetraponerines: a general synthesis and antiproliferative activity.</ArticleTitle><Pagination><MedlinePgn>3982-91</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jo500446f</ELocationID><Abstract><AbstractText>A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert-butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5-6-5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6-6-5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotoxic activity of (+)-T7 against breast carcinoma cell line MCF-7.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Bosque</LastName><ForeName>Irene</ForeName><Initials>I</Initials><Affiliation>Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante, Spain.</Affiliation></Author><Author ValidYN="Y"><LastName>Gonzalez-Gomez</LastName><ForeName>Jose C</ForeName><Initials>JC</Initials></Author><Author ValidYN="Y"><LastName>Loza</LastName><ForeName>María Isabel</ForeName><Initials>MI</Initials></Author><Author ValidYN="Y"><LastName>Brea</LastName><ForeName>José</ForeName><Initials>J</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType>Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2014</Year><Month>04</Month><Day>14</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="aheadofprint"><Year>2014</Year><Month>4</Month><Day>14</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2014</Year><Month>4</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2014</Year><Month>4</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2014</Year><Month>4</Month><Day>16</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="doi">10.1021/jo500446f</ArticleId><ArticleId IdType="pubmed">24731136</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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