Synthesis and biological evaluation of combretastatin A-4 and three combretastatin-based hybrids

ABSTRACT: The syntheses of combretastatin A-4 from gallic acid and of three combretastatin-based hybrids are described. Starting from commercial gallic acid, thephosphonium salt (3,4,5-trimethoxybenzylphosphonium bromide) is synthesized and coupled, through a Wittig reaction, with several aldehydes,...

Full description

Autores:
Agudelo Goméz, Lee Solbay
Tangarife Castaño, Verónica
Betancur Galvis, Liliana Amparo
Zapata Londoño, María Bibiana
Pérez Guaita, David
González, Miguel
Tipo de recurso:
Article of investigation
Fecha de publicación:
2012
Institución:
Universidad de Antioquia
Repositorio:
Repositorio UdeA
Idioma:
eng
OAI Identifier:
oai:bibliotecadigital.udea.edu.co:10495/41216
Acceso en línea:
https://hdl.handle.net/10495/41216
Palabra clave:
Antifúngicos
Antifungal Agents
Antivirales
Antiviral Agents
Biología Molecular
Molecular Biology
Estilbenos
Stilbenes
https://id.nlm.nih.gov/mesh/D000935
https://id.nlm.nih.gov/mesh/D000998
https://id.nlm.nih.gov/mesh/D008967
https://id.nlm.nih.gov/mesh/D013267
Rights
openAccess
License
http://creativecommons.org/licenses/by-nc/2.5/co/
id UDEA2_0634f9b94312ed247cc4985a2e0b21d7
oai_identifier_str oai:bibliotecadigital.udea.edu.co:10495/41216
network_acronym_str UDEA2
network_name_str Repositorio UdeA
repository_id_str
dc.title.spa.fl_str_mv Synthesis and biological evaluation of combretastatin A-4 and three combretastatin-based hybrids
title Synthesis and biological evaluation of combretastatin A-4 and three combretastatin-based hybrids
spellingShingle Synthesis and biological evaluation of combretastatin A-4 and three combretastatin-based hybrids
Antifúngicos
Antifungal Agents
Antivirales
Antiviral Agents
Biología Molecular
Molecular Biology
Estilbenos
Stilbenes
https://id.nlm.nih.gov/mesh/D000935
https://id.nlm.nih.gov/mesh/D000998
https://id.nlm.nih.gov/mesh/D008967
https://id.nlm.nih.gov/mesh/D013267
title_short Synthesis and biological evaluation of combretastatin A-4 and three combretastatin-based hybrids
title_full Synthesis and biological evaluation of combretastatin A-4 and three combretastatin-based hybrids
title_fullStr Synthesis and biological evaluation of combretastatin A-4 and three combretastatin-based hybrids
title_full_unstemmed Synthesis and biological evaluation of combretastatin A-4 and three combretastatin-based hybrids
title_sort Synthesis and biological evaluation of combretastatin A-4 and three combretastatin-based hybrids
dc.creator.fl_str_mv Agudelo Goméz, Lee Solbay
Tangarife Castaño, Verónica
Betancur Galvis, Liliana Amparo
Zapata Londoño, María Bibiana
Pérez Guaita, David
González, Miguel
dc.contributor.author.none.fl_str_mv Agudelo Goméz, Lee Solbay
Tangarife Castaño, Verónica
Betancur Galvis, Liliana Amparo
Zapata Londoño, María Bibiana
Pérez Guaita, David
González, Miguel
dc.contributor.researchgroup.spa.fl_str_mv GRID - Grupo de Investigación Dermatológica
dc.subject.decs.none.fl_str_mv Antifúngicos
Antifungal Agents
Antivirales
Antiviral Agents
Biología Molecular
Molecular Biology
Estilbenos
Stilbenes
topic Antifúngicos
Antifungal Agents
Antivirales
Antiviral Agents
Biología Molecular
Molecular Biology
Estilbenos
Stilbenes
https://id.nlm.nih.gov/mesh/D000935
https://id.nlm.nih.gov/mesh/D000998
https://id.nlm.nih.gov/mesh/D008967
https://id.nlm.nih.gov/mesh/D013267
dc.subject.meshuri.none.fl_str_mv https://id.nlm.nih.gov/mesh/D000935
https://id.nlm.nih.gov/mesh/D000998
https://id.nlm.nih.gov/mesh/D008967
https://id.nlm.nih.gov/mesh/D013267
description ABSTRACT: The syntheses of combretastatin A-4 from gallic acid and of three combretastatin-based hybrids are described. Starting from commercial gallic acid, thephosphonium salt (3,4,5-trimethoxybenzylphosphonium bromide) is synthesized and coupled, through a Wittig reaction, with several aldehydes, includingmethoxymethyl-protected isovanillin, the aldehyde γ-bicyclohomofarnesal having a labdane skeleton, 3-(3-pyridyl) propanal, and furfural. The biologicalproperties of the cis-coupled compounds as cytotoxic, antiviral and antifungal agents are also reported. In addition, pyrogallol, gallic and 3,4,5-trimethoxybenzoic acids have been studied biologically.
publishDate 2012
dc.date.issued.none.fl_str_mv 2012
dc.date.accessioned.none.fl_str_mv 2024-08-18T15:24:28Z
dc.date.available.none.fl_str_mv 2024-08-18T15:24:28Z
dc.type.spa.fl_str_mv Artículo de investigación
dc.type.coar.spa.fl_str_mv http://purl.org/coar/resource_type/c_2df8fbb1
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dc.identifier.citation.spa.fl_str_mv González MA, Pérez-Guaita D, Agudelo-Goméz LS, Tangarife-Castaño V, Zapata B, Betancur-Galvis L. Synthesis and Biological Evaluation of Combretastatin A-4 and Three Combretastatin-Based Hybrids. Natural Product Communications. 2012;7(8). doi:10.1177/1934578X1200700822
dc.identifier.issn.none.fl_str_mv 1934-578X
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/10495/41216
dc.identifier.doi.none.fl_str_mv 10.1177/1934578X1200700822
dc.identifier.eissn.none.fl_str_mv 1555-9475
identifier_str_mv González MA, Pérez-Guaita D, Agudelo-Goméz LS, Tangarife-Castaño V, Zapata B, Betancur-Galvis L. Synthesis and Biological Evaluation of Combretastatin A-4 and Three Combretastatin-Based Hybrids. Natural Product Communications. 2012;7(8). doi:10.1177/1934578X1200700822
1934-578X
10.1177/1934578X1200700822
1555-9475
url https://hdl.handle.net/10495/41216
dc.language.iso.spa.fl_str_mv eng
language eng
dc.relation.ispartofjournalabbrev.spa.fl_str_mv Nat. Prod. Commun.
dc.relation.citationendpage.spa.fl_str_mv 1056
dc.relation.citationissue.spa.fl_str_mv 8
dc.relation.citationstartpage.spa.fl_str_mv 1051
dc.relation.citationvolume.spa.fl_str_mv 7
dc.relation.ispartofjournal.spa.fl_str_mv Natural product communications
dc.rights.uri.*.fl_str_mv http://creativecommons.org/licenses/by-nc/2.5/co/
dc.rights.uri.spa.fl_str_mv https://creativecommons.org/licenses/by-nc/4.0/
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eu_rights_str_mv openAccess
dc.format.extent.spa.fl_str_mv 6 páginas
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.publisher.spa.fl_str_mv SAGE Publications
dc.publisher.place.spa.fl_str_mv Westerville, Estados Unidos
institution Universidad de Antioquia
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spelling Agudelo Goméz, Lee SolbayTangarife Castaño, VerónicaBetancur Galvis, Liliana AmparoZapata Londoño, María BibianaPérez Guaita, DavidGonzález, MiguelGRID - Grupo de Investigación Dermatológica2024-08-18T15:24:28Z2024-08-18T15:24:28Z2012González MA, Pérez-Guaita D, Agudelo-Goméz LS, Tangarife-Castaño V, Zapata B, Betancur-Galvis L. Synthesis and Biological Evaluation of Combretastatin A-4 and Three Combretastatin-Based Hybrids. Natural Product Communications. 2012;7(8). doi:10.1177/1934578X12007008221934-578Xhttps://hdl.handle.net/10495/4121610.1177/1934578X12007008221555-9475ABSTRACT: The syntheses of combretastatin A-4 from gallic acid and of three combretastatin-based hybrids are described. Starting from commercial gallic acid, thephosphonium salt (3,4,5-trimethoxybenzylphosphonium bromide) is synthesized and coupled, through a Wittig reaction, with several aldehydes, includingmethoxymethyl-protected isovanillin, the aldehyde γ-bicyclohomofarnesal having a labdane skeleton, 3-(3-pyridyl) propanal, and furfural. The biologicalproperties of the cis-coupled compounds as cytotoxic, antiviral and antifungal agents are also reported. In addition, pyrogallol, gallic and 3,4,5-trimethoxybenzoic acids have been studied biologically.COL00508396 páginasapplication/pdfengSAGE PublicationsWesterville, Estados Unidoshttp://creativecommons.org/licenses/by-nc/2.5/co/https://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Synthesis and biological evaluation of combretastatin A-4 and three combretastatin-based hybridsArtículo de investigaciónhttp://purl.org/coar/resource_type/c_2df8fbb1https://purl.org/redcol/resource_type/ARThttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionAntifúngicosAntifungal AgentsAntiviralesAntiviral AgentsBiología MolecularMolecular BiologyEstilbenosStilbeneshttps://id.nlm.nih.gov/mesh/D000935https://id.nlm.nih.gov/mesh/D000998https://id.nlm.nih.gov/mesh/D008967https://id.nlm.nih.gov/mesh/D013267Nat. Prod. 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