Synthesis of Heterocyclic Triads by Pd-Catalyzed Cross-Couplings and Evaluation of Their Cell-Specific Toxicity Profile
Identifieur interne : 001055 ( Main/Exploration ); précédent : 001054; suivant : 001056Synthesis of Heterocyclic Triads by Pd-Catalyzed Cross-Couplings and Evaluation of Their Cell-Specific Toxicity Profile
Auteurs : Joseph Salamoun [États-Unis] ; Shelby Anderson [États-Unis] ; James X0a C. Burnett [États-Unis] ; Rick Gussio [États-Unis] ; Peter Wipf [États-Unis]Source :
- Organic Letters [ 1523-7060 ] ; 2014.
Descripteurs français
- KwdFr :
- Acides boroniques (), Antinéoplasiques (), Antinéoplasiques (synthèse chimique), Antinéoplasiques (toxicité), Catalyse, Chimie organique (), Composés hétérocycliques (), Composés hétérocycliques (synthèse chimique), Composés hétérocycliques (toxicité), Furanes (), Humains, Oxazoles (), Palladium (), Relation structure-activité, Structure moléculaire, Tests de criblage d'agents antitumoraux.
- MESH :
- synthèse chimique : Antinéoplasiques, Composés hétérocycliques.
- toxicité : Antinéoplasiques, Composés hétérocycliques.
- Acides boroniques, Antinéoplasiques, Catalyse, Chimie organique, Composés hétérocycliques, Furanes, Humains, Oxazoles, Palladium, Relation structure-activité, Structure moléculaire, Tests de criblage d'agents antitumoraux.
English descriptors
- KwdEn :
- Antineoplastic Agents (chemical synthesis), Antineoplastic Agents (chemistry), Antineoplastic Agents (toxicity), Boronic Acids (chemistry), Catalysis, Chemistry, Organic (methods), Drug Screening Assays, Antitumor, Furans (chemistry), Heterocyclic Compounds (chemical synthesis), Heterocyclic Compounds (chemistry), Heterocyclic Compounds (toxicity), Humans, Molecular Structure, Oxazoles (chemistry), Palladium (chemistry), Structure-Activity Relationship.
- MESH :
- chemical , chemical synthesis : Antineoplastic Agents, Heterocyclic Compounds.
- chemical , chemistry : Antineoplastic Agents, Boronic Acids, Furans, Heterocyclic Compounds, Oxazoles, Palladium.
- chemical , toxicity : Antineoplastic Agents, Heterocyclic Compounds.
- methods : Chemistry, Organic.
- Catalysis, Drug Screening Assays, Antitumor, Humans, Molecular Structure, Structure-Activity Relationship.
Abstract
Two complementary approaches for the preparation of linked 5-membered heterocycles were developed. The Pd-catalyzed Suzuki–Miyaura cross-coupling with halogenated furan, thiophene, and selenophene led to higher overall yields, but C,H-bond activation was a more efficient strategy for the coupling at C(2) of oxazoles. Potency and selectivity of the final hydroxymethyl products in renal (A498), lung (NCI-H226), kidney (CAKI-1), and breast (MDA-MB-468, MCF7) carcinoma cell lines were determined.
Url:
DOI: 10.1021/ol500620m
PubMed: 24641272
PubMed Central: 3983320
Affiliations:
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Le document en format XML
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and Evaluation of Their Cell-Specific Toxicity Profile</title><author><name sortKey="Salamoun, Joseph" sort="Salamoun, Joseph" uniqKey="Salamoun J" first="Joseph" last="Salamoun">Joseph Salamoun</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry,<institution>University of Pittsburgh</institution>, Pittsburgh, Pennsylvania 15260,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Anderson, Shelby" sort="Anderson, Shelby" uniqKey="Anderson S" first="Shelby" last="Anderson">Shelby Anderson</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry,<institution>University of Pittsburgh</institution>, Pittsburgh, Pennsylvania 15260,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Burnett, James X0a C" sort="Burnett, James X0a C" uniqKey="Burnett J" first="James X0a C." last="Burnett">James X0a C. Burnett</name><affiliation wicri:level="1"><nlm:aff id="aff2"><institution>Leidos Biomedical Research, Inc.</institution>, Frederick National Laboratory for Cancer Research, Computational Drug Development Group, P.O. Box B, Frederick, Maryland 21702,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Gussio, Rick" sort="Gussio, Rick" uniqKey="Gussio R" first="Rick" last="Gussio">Rick Gussio</name><affiliation wicri:level="1"><nlm:aff id="aff3"><institution>Frederick National Laboratory for Cancer Research</institution>, Developmental Therapeutics Program, Computational Drug Development Group, P.O. Box B, Frederick, Maryland 21702,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Wipf, Peter" sort="Wipf, Peter" uniqKey="Wipf P" first="Peter" last="Wipf">Peter Wipf</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry,<institution>University of Pittsburgh</institution>, Pittsburgh, Pennsylvania 15260,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea><placeName><settlement type="city">Pittsburgh</settlement><region type="state">Pennsylvanie</region></placeName><orgName type="university" n="3">Université de Pittsburgh</orgName></affiliation></author></analytic><series><title level="j">Organic Letters</title><idno type="ISSN">1523-7060</idno><idno type="eISSN">1523-7052</idno><imprint><date when="2014">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antineoplastic Agents (chemical synthesis)</term><term>Antineoplastic Agents (chemistry)</term><term>Antineoplastic Agents (toxicity)</term><term>Boronic Acids (chemistry)</term><term>Catalysis</term><term>Chemistry, Organic (methods)</term><term>Drug Screening Assays, Antitumor</term><term>Furans (chemistry)</term><term>Heterocyclic Compounds (chemical synthesis)</term><term>Heterocyclic Compounds (chemistry)</term><term>Heterocyclic Compounds (toxicity)</term><term>Humans</term><term>Molecular Structure</term><term>Oxazoles (chemistry)</term><term>Palladium (chemistry)</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acides boroniques ()</term><term>Antinéoplasiques ()</term><term>Antinéoplasiques (synthèse chimique)</term><term>Antinéoplasiques (toxicité)</term><term>Catalyse</term><term>Chimie organique ()</term><term>Composés hétérocycliques ()</term><term>Composés hétérocycliques (synthèse chimique)</term><term>Composés hétérocycliques (toxicité)</term><term>Furanes ()</term><term>Humains</term><term>Oxazoles ()</term><term>Palladium ()</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Tests de criblage d'agents antitumoraux</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antineoplastic Agents</term><term>Heterocyclic Compounds</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antineoplastic Agents</term><term>Boronic Acids</term><term>Furans</term><term>Heterocyclic Compounds</term><term>Oxazoles</term><term>Palladium</term></keywords><keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Antineoplastic Agents</term><term>Heterocyclic Compounds</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Chemistry, Organic</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antinéoplasiques</term><term>Composés hétérocycliques</term></keywords><keywords scheme="MESH" qualifier="toxicité" xml:lang="fr"><term>Antinéoplasiques</term><term>Composés hétérocycliques</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalysis</term><term>Drug Screening Assays, Antitumor</term><term>Humans</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Acides boroniques</term><term>Antinéoplasiques</term><term>Catalyse</term><term>Chimie organique</term><term>Composés hétérocycliques</term><term>Furanes</term><term>Humains</term><term>Oxazoles</term><term>Palladium</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Tests de criblage d'agents antitumoraux</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p content-type="toc-graphic"><graphic xlink:href="ol-2014-00620m_0007" id="ab-d31e144"></graphic></p><p>Two complementary approaches for
the preparation of linked 5-membered
heterocycles were developed. The Pd-catalyzed Suzuki–Miyaura
cross-coupling with halogenated furan, thiophene, and selenophene
led to higher overall yields, but C,H-bond activation was a more efficient
strategy for the coupling at C(2) of oxazoles. Potency and selectivity
of the final hydroxymethyl products in renal (A498), lung (NCI-H226),
kidney (CAKI-1), and breast (MDA-MB-468, MCF7) carcinoma cell lines
were determined.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Ertl, P" uniqKey="Ertl P">P. Ertl</name></author><author><name sortKey="Jelfs, S" uniqKey="Jelfs S">S. Jelfs</name></author><author><name sortKey="Muhlbacher, J" uniqKey="Muhlbacher J">J. Mühlbacher</name></author><author><name sortKey="Schuffenhauer, A" uniqKey="Schuffenhauer A">A. Schuffenhauer</name></author><author><name sortKey="Selzer, P" uniqKey="Selzer P">P. Selzer</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Jin, Z" uniqKey="Jin Z">Z. Jin</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wipf, P" uniqKey="Wipf P">P. Wipf</name></author><author><name sortKey="Halter, R J" uniqKey="Halter R">R. J. Halter</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wakefield, B" uniqKey="Wakefield B">B. 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Komatsu</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Skepper, C K" uniqKey="Skepper C">C. K. Skepper</name></author><author><name sortKey="Quach, T" uniqKey="Quach T">T. Quach</name></author><author><name sortKey="Molinski, T F" uniqKey="Molinski T">T. F. Molinski</name></author></analytic></biblStruct><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="Vedejs, E" uniqKey="Vedejs E">E. Vedejs</name></author><author><name sortKey="Luchetta, L" uniqKey="Luchetta L">L. Luchetta</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Verrier, C" uniqKey="Verrier C">C. Verrier</name></author><author><name sortKey="Martin, T" uniqKey="Martin T">T. Martin</name></author><author><name sortKey="Hoarau, C" uniqKey="Hoarau C">C. Hoarau</name></author><author><name sortKey="Marsais, F" uniqKey="Marsais F">F. Marsais</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Shoemaker, R H" uniqKey="Shoemaker R">R. H. Shoemaker</name></author></analytic></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>États-Unis</li></country><region><li>Pennsylvanie</li></region><settlement><li>Pittsburgh</li></settlement><orgName><li>Université de Pittsburgh</li></orgName></list><tree><country name="États-Unis"><noRegion><name sortKey="Salamoun, Joseph" sort="Salamoun, Joseph" uniqKey="Salamoun J" first="Joseph" last="Salamoun">Joseph Salamoun</name></noRegion><name sortKey="Anderson, Shelby" sort="Anderson, Shelby" uniqKey="Anderson S" first="Shelby" last="Anderson">Shelby Anderson</name><name sortKey="Burnett, James X0a C" sort="Burnett, James X0a C" uniqKey="Burnett J" first="James X0a C." last="Burnett">James X0a C. Burnett</name><name sortKey="Gussio, Rick" sort="Gussio, Rick" uniqKey="Gussio R" first="Rick" last="Gussio">Rick Gussio</name><name sortKey="Wipf, Peter" sort="Wipf, Peter" uniqKey="Wipf P" first="Peter" last="Wipf">Peter Wipf</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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