New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation
ABSTARCT: Several terpenylquinones derived from 1,4-anthracenedione (1,4-anthracenequinone, AQ) have been prepared by addition or substitution nucleophilic reactions and further transformed into extended polycyclic systems, which mainly kept the 1,4-quinone moiety fused to different nitrogen-heteroc...
- Autores:
-
Roa Linares, Vicky Constanza
Gamito, Ana Maria
Castro, Maria Angeles
Mesa Arango, Ana Cecilia
Martin, Arturo San Feliciano
Tangarife Castano, Veronica
Betancur Galvis, Liliana Amparo
Del Corral, Jose Maria Migel
Francesch, Andres
- Tipo de recurso:
- Article of investigation
- Fecha de publicación:
- 2015
- Institución:
- Universidad de Antioquia
- Repositorio:
- Repositorio UdeA
- Idioma:
- eng
- OAI Identifier:
- oai:bibliotecadigital.udea.edu.co:10495/11490
- Acceso en línea:
- http://hdl.handle.net/10495/11490
- Palabra clave:
- Organic compounds
Antineoplastic
Antiviral activities
Biological evaluation
Filamentous fungi
Heterocyclic rings
Nucleophilic reaction
Polycyclic systems
Quinoxalines
- Rights
- openAccess
- License
- Atribución 2.5
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| dc.title.spa.fl_str_mv |
New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation |
| dc.title.alternative.spa.fl_str_mv |
Roa Linares et al. New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation |
| title |
New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation |
| spellingShingle |
New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation Organic compounds Antineoplastic Antiviral activities Biological evaluation Filamentous fungi Heterocyclic rings Nucleophilic reaction Polycyclic systems Quinoxalines |
| title_short |
New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation |
| title_full |
New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation |
| title_fullStr |
New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation |
| title_full_unstemmed |
New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation |
| title_sort |
New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation |
| dc.creator.fl_str_mv |
Roa Linares, Vicky Constanza Gamito, Ana Maria Castro, Maria Angeles Mesa Arango, Ana Cecilia Martin, Arturo San Feliciano Tangarife Castano, Veronica Betancur Galvis, Liliana Amparo Del Corral, Jose Maria Migel Francesch, Andres |
| dc.contributor.author.none.fl_str_mv |
Roa Linares, Vicky Constanza Gamito, Ana Maria Castro, Maria Angeles Mesa Arango, Ana Cecilia Martin, Arturo San Feliciano Tangarife Castano, Veronica Betancur Galvis, Liliana Amparo Del Corral, Jose Maria Migel Francesch, Andres |
| dc.subject.none.fl_str_mv |
Organic compounds Antineoplastic Antiviral activities Biological evaluation Filamentous fungi Heterocyclic rings Nucleophilic reaction Polycyclic systems Quinoxalines |
| topic |
Organic compounds Antineoplastic Antiviral activities Biological evaluation Filamentous fungi Heterocyclic rings Nucleophilic reaction Polycyclic systems Quinoxalines |
| description |
ABSTARCT: Several terpenylquinones derived from 1,4-anthracenedione (1,4-anthracenequinone, AQ) have been prepared by addition or substitution nucleophilic reactions and further transformed into extended polycyclic systems, which mainly kept the 1,4-quinone moiety fused to different nitrogen-heterocyclic rings (pyrrole, imidazole, pyrazine or quinoxaline) into the structure. The compounds synthesized were evaluated for their antineoplastic, antifungal and antiviral activities. GI50 antineoplastic values remained under μM levels for AQs, while the heterocyclic derivatives showed antifungal MIC values in the low μg mL-1 range against yeasts and filamentous fungi. Only few compounds displayed a discrete non-selective antiherpetic activity in the μg mL-1 range. This journal is © The Royal Society of Chemistry 2015. |
| publishDate |
2015 |
| dc.date.issued.none.fl_str_mv |
2015 |
| dc.date.accessioned.none.fl_str_mv |
2019-07-23T14:40:08Z |
| dc.date.available.none.fl_str_mv |
2019-07-23T14:40:08Z |
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info:eu-repo/semantics/article |
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http://purl.org/coar/version/c_970fb48d4fbd8a85 |
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info:eu-repo/semantics/publishedVersion |
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http://purl.org/coar/resource_type/c_2df8fbb1 |
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https://purl.org/redcol/resource_type/ART |
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Artículo de investigación |
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http://purl.org/coar/resource_type/c_2df8fbb1 |
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publishedVersion |
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Roa Linares VC et al. New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation. RSC Advances. 2015;5(2):1244-1261 |
| dc.identifier.issn.none.fl_str_mv |
2046-2069 |
| dc.identifier.uri.none.fl_str_mv |
http://hdl.handle.net/10495/11490 |
| dc.identifier.doi.none.fl_str_mv |
10.1039/c4ra11726c |
| identifier_str_mv |
Roa Linares VC et al. New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation. RSC Advances. 2015;5(2):1244-1261 2046-2069 10.1039/c4ra11726c |
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http://hdl.handle.net/10495/11490 |
| dc.language.iso.spa.fl_str_mv |
eng |
| language |
eng |
| dc.relation.ispartofjournalabbrev.spa.fl_str_mv |
RSC Advances |
| dc.rights.*.fl_str_mv |
Atribución 2.5 |
| dc.rights.spa.fl_str_mv |
info:eu-repo/semantics/openAccess |
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http://creativecommons.org/licenses/by/2.5/co/ |
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Royal Society of Chemistry |
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Reino Unido |
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Universidad de Antioquia |
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Roa Linares, Vicky ConstanzaGamito, Ana MariaCastro, Maria AngelesMesa Arango, Ana CeciliaMartin, Arturo San FelicianoTangarife Castano, VeronicaBetancur Galvis, Liliana AmparoDel Corral, Jose Maria MigelFrancesch, Andres2019-07-23T14:40:08Z2019-07-23T14:40:08Z2015Roa Linares VC et al. New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluation. RSC Advances. 2015;5(2):1244-12612046-2069http://hdl.handle.net/10495/1149010.1039/c4ra11726cABSTARCT: Several terpenylquinones derived from 1,4-anthracenedione (1,4-anthracenequinone, AQ) have been prepared by addition or substitution nucleophilic reactions and further transformed into extended polycyclic systems, which mainly kept the 1,4-quinone moiety fused to different nitrogen-heterocyclic rings (pyrrole, imidazole, pyrazine or quinoxaline) into the structure. The compounds synthesized were evaluated for their antineoplastic, antifungal and antiviral activities. GI50 antineoplastic values remained under μM levels for AQs, while the heterocyclic derivatives showed antifungal MIC values in the low μg mL-1 range against yeasts and filamentous fungi. Only few compounds displayed a discrete non-selective antiherpetic activity in the μg mL-1 range. This journal is © The Royal Society of Chemistry 2015.17application/pdfengRoyal Society of ChemistryReino Unidoinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_2df8fbb1https://purl.org/redcol/resource_type/ARTArtículo de investigaciónhttp://purl.org/coar/version/c_970fb48d4fbd8a85Atribución 2.5info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/2.5/co/http://purl.org/coar/access_right/c_abf2https://creativecommons.org/licenses/by/4.0/Organic compoundsAntineoplasticAntiviral activitiesBiological evaluationFilamentous fungiHeterocyclic ringsNucleophilic reactionPolycyclic systemsQuinoxalinesNew 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluationRoa Linares et al. New 1,4-anthracenedione derivatives with fused heterocyclic rings: Synthesis and biological evaluationRSC AdvancesRoyal Society of Chemistry1244126152ORIGINALCastroMariaAngeles_2015_AnthracenedioneHeteocyclicBiological.pdfCastroMariaAngeles_2015_AnthracenedioneHeteocyclicBiological.pdfArtículo de Revistaapplication/pdf624934http://bibliotecadigital.udea.edu.co/bitstream/10495/11490/1/CastroMariaAngeles_2015_AnthracenedioneHeteocyclicBiological.pdfd77f6ef8f9fa9f92942cff13b4e9d7caMD51CC-LICENSElicense_urllicense_urltext/plain; charset=utf-849http://bibliotecadigital.udea.edu.co/bitstream/10495/11490/2/license_url4afdbb8c545fd630ea7db775da747b2fMD52license_textlicense_texttext/html; charset=utf-80http://bibliotecadigital.udea.edu.co/bitstream/10495/11490/3/license_textd41d8cd98f00b204e9800998ecf8427eMD53license_rdflicense_rdfapplication/rdf+xml; charset=utf-80http://bibliotecadigital.udea.edu.co/bitstream/10495/11490/4/license_rdfd41d8cd98f00b204e9800998ecf8427eMD54LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://bibliotecadigital.udea.edu.co/bitstream/10495/11490/5/license.txt8a4605be74aa9ea9d79846c1fba20a33MD5510495/11490oai:bibliotecadigital.udea.edu.co:10495/114902021-03-24 20:49:43.714Repositorio Institucional Universidad de Antioquiaandres.perez@udea.edu.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 |