A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin
Identifieur interne : 000484 ( Pmc/Checkpoint ); précédent : 000483; suivant : 000485A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin
Auteurs : Anna Carbone [Italie] ; Virginia Span [Italie] ; Barbara Parrino [Italie] ; Cristina Ciancimino [Italie] ; Orazio A. Attanasi [Italie] ; Gianfranco Favi [Italie]Source :
- Molecules [ 1420-3049 ] ; 2013.
Abstract
A series of substituted ethyl 1-[(
Url:
DOI: 10.3390/molecules18032518
PubMed: 23442928
PubMed Central: 6269752
Affiliations:
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<front><div type="abstract" xml:lang="en"><p>A series of substituted ethyl 1-[(<italic>tert</italic>
-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1<italic>H</italic>
-indol-3-yl)-4-[(1-methyl-1<italic>H</italic>
-indol-3-yl)carbonyl]-1<italic>H</italic>
-pyrrole-3-carboxylates were prepared in excellent yields (82-98%) by one-pot reactions between β-dicarbonyl compounds <bold>12a</bold>
–<bold>e</bold>
and 1,2-diaza-1,3-diene (DD) <bold>13</bold>
. Derivatives <bold>10a</bold>
,<bold>c</bold>
–<bold>e</bold>
, deazaanalogues of the bis-indole alkaloid topsentin, screened by the National Cancer Institute (Bethesda, MD, USA) in the <italic>in vitro</italic>
one dose primary anticancer assay against a panel of about 60 human tumor cell lines, showed no significant activity, with the exception of compound <bold>9e</bold>
, which showed moderate activity against the HOP-92 cell line of the non small cell lung cancer sub-panel and the SNB-75 cell line of the CNS sub-panel.</p>
</div>
</front>
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</TEI>
<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Molecules</journal-id>
<journal-id journal-id-type="iso-abbrev">Molecules</journal-id>
<journal-id journal-id-type="publisher-id">molecules</journal-id>
<journal-title-group><journal-title>Molecules</journal-title>
</journal-title-group>
<issn pub-type="epub">1420-3049</issn>
<publisher><publisher-name>MDPI</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">23442928</article-id>
<article-id pub-id-type="pmc">6269752</article-id>
<article-id pub-id-type="doi">10.3390/molecules18032518</article-id>
<article-id pub-id-type="publisher-id">molecules-18-02518</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Article</subject>
</subj-group>
</article-categories>
<title-group><article-title>A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin</article-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Carbone</surname>
<given-names>Anna</given-names>
</name>
<xref ref-type="aff" rid="af1-molecules-18-02518">1</xref>
<xref rid="c1-molecules-18-02518" ref-type="corresp">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Spanò</surname>
<given-names>Virginia</given-names>
</name>
<xref ref-type="aff" rid="af1-molecules-18-02518">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Parrino</surname>
<given-names>Barbara</given-names>
</name>
<xref ref-type="aff" rid="af1-molecules-18-02518">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Ciancimino</surname>
<given-names>Cristina</given-names>
</name>
<xref ref-type="aff" rid="af1-molecules-18-02518">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Attanasi</surname>
<given-names>Orazio A.</given-names>
</name>
<xref ref-type="aff" rid="af2-molecules-18-02518">2</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Favi</surname>
<given-names>Gianfranco</given-names>
</name>
<xref ref-type="aff" rid="af2-molecules-18-02518">2</xref>
<xref rid="c1-molecules-18-02518" ref-type="corresp">*</xref>
</contrib>
</contrib-group>
<aff id="af1-molecules-18-02518"><label>1</label>
Dipartimento di Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche, Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy</aff>
<aff id="af2-molecules-18-02518"><label>2</label>
Dipartimento di Scienze Biomolecolari, Università degli Studi di Urbino “Carlo Bo”, Via I Maggetti 24, 61029 Urbino, Italy</aff>
<author-notes><corresp id="c1-molecules-18-02518"><label>*</label>
Authors to whom correspondence should be addressed; E-Mails: <email>anna.carbone@unipa.it</email>
(A.C.); <email>gianfranco.favi@uniurb.it</email>
(G.F.); Tel.: +39-091-23896826 (A.C.); Fax: +39-091-23860854 (A.C.); Tel.: +39-0722-303440 (G.F.).</corresp>
</author-notes>
<pub-date pub-type="epub"><day>26</day>
<month>2</month>
<year>2013</year>
</pub-date>
<pub-date pub-type="collection"><month>3</month>
<year>2013</year>
</pub-date>
<volume>18</volume>
<issue>3</issue>
<fpage>2518</fpage>
<lpage>2527</lpage>
<history><date date-type="received"><day>21</day>
<month>1</month>
<year>2013</year>
</date>
<date date-type="rev-recd"><day>31</day>
<month>1</month>
<year>2013</year>
</date>
<date date-type="accepted"><day>07</day>
<month>2</month>
<year>2013</year>
</date>
</history>
<permissions><copyright-statement>© 2013 by the authors; licensee MDPI, Basel, Switzerland.</copyright-statement>
<copyright-year>2013</copyright-year>
<license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/3.0/"><license-p><pmc-comment>CREATIVE COMMONS</pmc-comment>
This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/3.0/">http://creativecommons.org/licenses/by/3.0/</ext-link>
).</license-p>
</license>
</permissions>
<abstract><p>A series of substituted ethyl 1-[(<italic>tert</italic>
-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1<italic>H</italic>
-indol-3-yl)-4-[(1-methyl-1<italic>H</italic>
-indol-3-yl)carbonyl]-1<italic>H</italic>
-pyrrole-3-carboxylates were prepared in excellent yields (82-98%) by one-pot reactions between β-dicarbonyl compounds <bold>12a</bold>
–<bold>e</bold>
and 1,2-diaza-1,3-diene (DD) <bold>13</bold>
. Derivatives <bold>10a</bold>
,<bold>c</bold>
–<bold>e</bold>
, deazaanalogues of the bis-indole alkaloid topsentin, screened by the National Cancer Institute (Bethesda, MD, USA) in the <italic>in vitro</italic>
one dose primary anticancer assay against a panel of about 60 human tumor cell lines, showed no significant activity, with the exception of compound <bold>9e</bold>
, which showed moderate activity against the HOP-92 cell line of the non small cell lung cancer sub-panel and the SNB-75 cell line of the CNS sub-panel.</p>
</abstract>
<kwd-group><kwd>topsentin</kwd>
<kwd>bis-indole alkaloids</kwd>
<kwd>antitumor activity</kwd>
<kwd>ethyl 1-[(<italic>tert</italic>
-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1<italic>H</italic>
-indol-3-yl)-4-[(1-methyl-1<italic>H</italic>
-indol-3-yl)-carbonyl]-1<italic>H</italic>
-pyrrole-3-carboxylates</kwd>
</kwd-group>
</article-meta>
</front>
</pmc>
<affiliations><list><country><li>Italie</li>
</country>
<region><li>Sicile</li>
</region>
<settlement><li>Palerme</li>
</settlement>
<orgName><li>Université de Palerme</li>
</orgName>
</list>
<tree><country name="Italie"><region name="Sicile"><name sortKey="Carbone, Anna" sort="Carbone, Anna" uniqKey="Carbone A" first="Anna" last="Carbone">Anna Carbone</name>
</region>
<name sortKey="Attanasi, Orazio A" sort="Attanasi, Orazio A" uniqKey="Attanasi O" first="Orazio A." last="Attanasi">Orazio A. Attanasi</name>
<name sortKey="Ciancimino, Cristina" sort="Ciancimino, Cristina" uniqKey="Ciancimino C" first="Cristina" last="Ciancimino">Cristina Ciancimino</name>
<name sortKey="Favi, Gianfranco" sort="Favi, Gianfranco" uniqKey="Favi G" first="Gianfranco" last="Favi">Gianfranco Favi</name>
<name sortKey="Parrino, Barbara" sort="Parrino, Barbara" uniqKey="Parrino B" first="Barbara" last="Parrino">Barbara Parrino</name>
<name sortKey="Span, Virginia" sort="Span, Virginia" uniqKey="Span V" first="Virginia" last="Span">Virginia Span</name>
</country>
</tree>
</affiliations>
</record>
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