Mostrar el registro sencillo del ítem
dc.contributor.author
Derita, Marcos Gabriel
dc.contributor.author
Montenegro, Ivan
dc.contributor.author
Garibotto, Francisco Matías
dc.contributor.author
Enriz, Ricardo Daniel
dc.contributor.author
Cuellar Fritis, Mauricio
dc.contributor.author
Zacchino, Susana Alicia Stella
dc.date.available
2015-08-04T19:38:33Z
dc.date.issued
2013-02-05
dc.identifier.citation
Derita, Marcos Gabriel; Montenegro, Ivan; Garibotto, Francisco Matías; Enriz, Ricardo Daniel; Cuellar Fritis, Mauricio; et al.; Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies; Molecular Diversity Preservation International; Molecules; 18; 5-2-2013; 2029-2051
dc.identifier.issn
1420-3049
dc.identifier.uri
http://hdl.handle.net/11336/1543
dc.description.abstract
Seventeen drimanes including polygodial (1), isopolygodial (2), drimenol (3) and confertifolin (4) obtained from natural sources and the semi-synthetic derivatives 5?17 obtained from 1?3, were evaluated in vitro for antifungal properties against a unique panel of fungi with standardized procedures by using two end-points, MIC100 and MIC50. A SAR analysis of the whole series, supported by conformational and electronic studies, allowed us to show that the Δ7,8 -double bond would be one of the key structural features related to the antifungal activity. The MEPs obtained for active compounds exhibit a clear negative minimum value (deep red zone) in the vicinity of the Δ7,8 -double bond, which is not present in the inactive ones. Apart of this negative zone, a positive region (deep blue) appears in 1, which is not observed either in its epimer 2 nor in the rest of the active compounds. The LogP of active compounds varies between 2.33 and 3.84, but differences in MICs are not correlated with concomitant variations in LogP values.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Molecular Diversity Preservation International
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Antifungal Agents
dc.subject
Drimanes
dc.subject
Structure-Activity Relationships
dc.subject
Stereo-Electronic Studies
dc.subject.classification
Química Orgánica
dc.subject.classification
Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.subject.classification
Bioquímica y Biología Molecular
dc.subject.classification
Ciencias Biológicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2016-03-30 10:35:44.97925-03
dc.journal.volume
18
dc.journal.pagination
2029-2051
dc.journal.pais
Suiza
dc.journal.ciudad
Basel
dc.description.fil
Fil: Derita, Marcos Gabriel. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina.; Universidad Nacional del Litoral. Facultad de Ciencias Agrarias. Departamento de Producción Vegetal. Cátedra de Cultivos Intensivos; Argentina;
dc.description.fil
Fil: Montenegro, Ivan. Universidad de Valparaíso. Facultad de Farmacia. Laboratorio de Ciencias Químicas y Recursos Naturales; Chile.;
dc.description.fil
Fil: Garibotto, Francisco Matías. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico - CONICET - San Luis. Instituto Multidiciplinario de Investigación Biológica de San Luis; Argentina; Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia; Argentina;
dc.description.fil
Fil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina.; Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico -CONICET - San Luis. Instituto Multidisciplinario de Investigación Biológica de San Luis; Argentina.;
dc.description.fil
Fil: Cuellar Fritis, Mauricio. Universidad de Valparaíso. Facultad de Farmacia. Laboratorio de Ciencias Químicas y Recursos Naturales; Chile.;
dc.description.fil
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina.;
dc.journal.title
Molecules
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://www.mdpi.com/1420-3049/18/2/2029
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/doi:10.3390/molecules18022029
Archivos asociados