SYNTHESIS AND CONFORMATIONAL ANALYSIS OF LEPTOCARPIN DERIVATIVES: INFLUENCE OF MODIFICATION OF THE OXIRANE RINGON LEPTOCARPIN'S CYTOTOXIC ACTIVITY

SYNTHESIS AND CONFORMATIONAL ANALYSIS OF LEPTOCARPIN DERIVATIVES: INFLUENCE OF MODIFICATION OF THE OXIRANE RINGON LEPTOCARPIN'S CYTOTOXIC ACTIVITY

The reaction in acidconditions of Leptocarpin 1, a compound with antitumor activity, formed two new isomeric products, 8b-angeloyl-1b,3b-dihydroxy-4,10-dimethyl,-D11(13) methylen-4Z,9Z-dieneheliangol-6,12-olide 2 and 8b-angeloyl-1b,3b-dihydroxy-4-methyl-D11(13),D11(14)-dimethylen-4Z-eneheliangol-6,1...

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Autores principales: MARTÍNEZ,ROLANDO, KESTERNICH,VICTOR, CARRACSO,HÉCTOR, ÁLVAREZ-CONTRERAS,CAROLINA, MONTENEGRO,CAROLINA, UGARTE,RICARDO, GUTIÉRREZ,ELENA, MORENO,JOSÉ, GARCÍA,CARLOS, WERNER,ENRIQUE, CÁRCAMOS,JUAN
Lenguaje:English
Publicado: Sociedad Chilena de Química 2006
Materias:
Conformational analysis
Heliangolide
Sesquiterpene lactones
Cytotoxicity
Acceso en línea:http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072006000400003
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spelling oai:scielo:S0717-970720060004000032007-03-08SYNTHESIS AND CONFORMATIONAL ANALYSIS OF LEPTOCARPIN DERIVATIVES: INFLUENCE OF MODIFICATION OF THE OXIRANE RINGON LEPTOCARPIN'S CYTOTOXIC ACTIVITYMARTÍNEZ,ROLANDOKESTERNICH,VICTORCARRACSO,HÉCTORÁLVAREZ-CONTRERAS,CAROLINAMONTENEGRO,CAROLINAUGARTE,RICARDOGUTIÉRREZ,ELENAMORENO,JOSÉGARCÍA,CARLOSWERNER,ENRIQUECÁRCAMOS,JUAN Conformational analysis Heliangolide Sesquiterpene lactones Cytotoxicity The reaction in acidconditions of Leptocarpin 1, a compound with antitumor activity, formed two new isomeric products, 8b-angeloyl-1b,3b-dihydroxy-4,10-dimethyl,-D11(13) methylen-4Z,9Z-dieneheliangol-6,12-olide 2 and 8b-angeloyl-1b,3b-dihydroxy-4-methyl-D11(13),D11(14)-dimethylen-4Z-eneheliangol-6,12-olide 3, whose structures reported in this study were established by spectroscopy (¹H-NMR, 13C-NMR, MS and IR) and confirmedthrough ROESY experiments and theoretical studies by molecular mechanics. The in vitro cytotoxicity of these isomeric compounds was less active than leptocarpin, showing the importance of the oxirane ring in the biological activity. Cytotoxic activity was measured in six cancer cell linesinfo:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.51 n.4 20062006-12-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072006000400003en10.4067/S0717-97072006000400003
institution Scielo Chile
collection Scielo Chile
language English
topic Conformational analysis
Heliangolide
Sesquiterpene lactones
Cytotoxicity
spellingShingle Conformational analysis
Heliangolide
Sesquiterpene lactones
Cytotoxicity
MARTÍNEZ,ROLANDO
KESTERNICH,VICTOR
CARRACSO,HÉCTOR
ÁLVAREZ-CONTRERAS,CAROLINA
MONTENEGRO,CAROLINA
UGARTE,RICARDO
GUTIÉRREZ,ELENA
MORENO,JOSÉ
GARCÍA,CARLOS
WERNER,ENRIQUE
CÁRCAMOS,JUAN
SYNTHESIS AND CONFORMATIONAL ANALYSIS OF LEPTOCARPIN DERIVATIVES: INFLUENCE OF MODIFICATION OF THE OXIRANE RINGON LEPTOCARPIN'S CYTOTOXIC ACTIVITY
description The reaction in acidconditions of Leptocarpin 1, a compound with antitumor activity, formed two new isomeric products, 8b-angeloyl-1b,3b-dihydroxy-4,10-dimethyl,-D11(13) methylen-4Z,9Z-dieneheliangol-6,12-olide 2 and 8b-angeloyl-1b,3b-dihydroxy-4-methyl-D11(13),D11(14)-dimethylen-4Z-eneheliangol-6,12-olide 3, whose structures reported in this study were established by spectroscopy (¹H-NMR, 13C-NMR, MS and IR) and confirmedthrough ROESY experiments and theoretical studies by molecular mechanics. The in vitro cytotoxicity of these isomeric compounds was less active than leptocarpin, showing the importance of the oxirane ring in the biological activity. Cytotoxic activity was measured in six cancer cell lines
author MARTÍNEZ,ROLANDO
KESTERNICH,VICTOR
CARRACSO,HÉCTOR
ÁLVAREZ-CONTRERAS,CAROLINA
MONTENEGRO,CAROLINA
UGARTE,RICARDO
GUTIÉRREZ,ELENA
MORENO,JOSÉ
GARCÍA,CARLOS
WERNER,ENRIQUE
CÁRCAMOS,JUAN
author_facet MARTÍNEZ,ROLANDO
KESTERNICH,VICTOR
CARRACSO,HÉCTOR
ÁLVAREZ-CONTRERAS,CAROLINA
MONTENEGRO,CAROLINA
UGARTE,RICARDO
GUTIÉRREZ,ELENA
MORENO,JOSÉ
GARCÍA,CARLOS
WERNER,ENRIQUE
CÁRCAMOS,JUAN
author_sort MARTÍNEZ,ROLANDO
title SYNTHESIS AND CONFORMATIONAL ANALYSIS OF LEPTOCARPIN DERIVATIVES: INFLUENCE OF MODIFICATION OF THE OXIRANE RINGON LEPTOCARPIN'S CYTOTOXIC ACTIVITY
title_short SYNTHESIS AND CONFORMATIONAL ANALYSIS OF LEPTOCARPIN DERIVATIVES: INFLUENCE OF MODIFICATION OF THE OXIRANE RINGON LEPTOCARPIN'S CYTOTOXIC ACTIVITY
title_full SYNTHESIS AND CONFORMATIONAL ANALYSIS OF LEPTOCARPIN DERIVATIVES: INFLUENCE OF MODIFICATION OF THE OXIRANE RINGON LEPTOCARPIN'S CYTOTOXIC ACTIVITY
title_fullStr SYNTHESIS AND CONFORMATIONAL ANALYSIS OF LEPTOCARPIN DERIVATIVES: INFLUENCE OF MODIFICATION OF THE OXIRANE RINGON LEPTOCARPIN'S CYTOTOXIC ACTIVITY
title_full_unstemmed SYNTHESIS AND CONFORMATIONAL ANALYSIS OF LEPTOCARPIN DERIVATIVES: INFLUENCE OF MODIFICATION OF THE OXIRANE RINGON LEPTOCARPIN'S CYTOTOXIC ACTIVITY
title_sort synthesis and conformational analysis of leptocarpin derivatives: influence of modification of the oxirane ringon leptocarpin's cytotoxic activity
publisher Sociedad Chilena de Química
publishDate 2006
url http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072006000400003
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