Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone
- Autores
- Di Chenna, Pablo Hector; Benedetti Doctorovich, Violeta; Baggio, Ricardo Fortunato; Garland, María T.; Burton, Gerardo
- Año de publicación
- 2001
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- A regio- and stereospecific synthesis of monoarylimino o-quinones derived from β-lapachone (1) was achieved by treatment of the quinone with a slight excess of an arylamine in the presence of an excess of triethylamine/titanium tetrachloride 4:1. Imine formation occurred exclusively at position 6, giving the Z diastereomer, as determined by single-crystal X-ray analysis. In vitro tests for cytotoxicity in 55 human cancer cell cultures showed a substantial loss in activity for the p-nitrophenylimine (5), whereas the phenylimine (2), p-methylphenylimine (3), and p-methoxyphenylimine (4) retained (or bettered) most of the cytotoxicity and selectivity of the parent quinone. Preliminary in vivo testing in hollow fiber assays against a standard panel of 12 human tumor cell lines showed that although β-lapachone failed, compounds 2 and 3 had good scores with net cell kills.
Fil: Di Chenna, Pablo Hector. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Benedetti Doctorovich, Violeta. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica; Argentina
Fil: Garland, María T.. Universidad de Chile; Chile
Fil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina - Materia
-
BETA-LAPACHONE
CYTOTOXICITY - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/86463
Ver los metadatos del registro completo
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Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachoneDi Chenna, Pablo HectorBenedetti Doctorovich, VioletaBaggio, Ricardo FortunatoGarland, María T.Burton, GerardoBETA-LAPACHONECYTOTOXICITYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A regio- and stereospecific synthesis of monoarylimino o-quinones derived from β-lapachone (1) was achieved by treatment of the quinone with a slight excess of an arylamine in the presence of an excess of triethylamine/titanium tetrachloride 4:1. Imine formation occurred exclusively at position 6, giving the Z diastereomer, as determined by single-crystal X-ray analysis. In vitro tests for cytotoxicity in 55 human cancer cell cultures showed a substantial loss in activity for the p-nitrophenylimine (5), whereas the phenylimine (2), p-methylphenylimine (3), and p-methoxyphenylimine (4) retained (or bettered) most of the cytotoxicity and selectivity of the parent quinone. Preliminary in vivo testing in hollow fiber assays against a standard panel of 12 human tumor cell lines showed that although β-lapachone failed, compounds 2 and 3 had good scores with net cell kills.Fil: Di Chenna, Pablo Hector. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Benedetti Doctorovich, Violeta. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica; ArgentinaFil: Garland, María T.. Universidad de Chile; ChileFil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaAmerican Chemical Society2001-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/86463Di Chenna, Pablo Hector; Benedetti Doctorovich, Violeta; Baggio, Ricardo Fortunato; Garland, María T.; Burton, Gerardo; Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone; American Chemical Society; Journal of Medicinal Chemistry; 44; 15; 7-2001; 2486-24890022-2623CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jm010050uinfo:eu-repo/semantics/altIdentifier/doi/10.1021/jm010050uinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:03:08Zoai:ri.conicet.gov.ar:11336/86463instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:03:08.795CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone |
title |
Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone |
spellingShingle |
Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone Di Chenna, Pablo Hector BETA-LAPACHONE CYTOTOXICITY |
title_short |
Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone |
title_full |
Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone |
title_fullStr |
Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone |
title_full_unstemmed |
Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone |
title_sort |
Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone |
dc.creator.none.fl_str_mv |
Di Chenna, Pablo Hector Benedetti Doctorovich, Violeta Baggio, Ricardo Fortunato Garland, María T. Burton, Gerardo |
author |
Di Chenna, Pablo Hector |
author_facet |
Di Chenna, Pablo Hector Benedetti Doctorovich, Violeta Baggio, Ricardo Fortunato Garland, María T. Burton, Gerardo |
author_role |
author |
author2 |
Benedetti Doctorovich, Violeta Baggio, Ricardo Fortunato Garland, María T. Burton, Gerardo |
author2_role |
author author author author |
dc.subject.none.fl_str_mv |
BETA-LAPACHONE CYTOTOXICITY |
topic |
BETA-LAPACHONE CYTOTOXICITY |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
A regio- and stereospecific synthesis of monoarylimino o-quinones derived from β-lapachone (1) was achieved by treatment of the quinone with a slight excess of an arylamine in the presence of an excess of triethylamine/titanium tetrachloride 4:1. Imine formation occurred exclusively at position 6, giving the Z diastereomer, as determined by single-crystal X-ray analysis. In vitro tests for cytotoxicity in 55 human cancer cell cultures showed a substantial loss in activity for the p-nitrophenylimine (5), whereas the phenylimine (2), p-methylphenylimine (3), and p-methoxyphenylimine (4) retained (or bettered) most of the cytotoxicity and selectivity of the parent quinone. Preliminary in vivo testing in hollow fiber assays against a standard panel of 12 human tumor cell lines showed that although β-lapachone failed, compounds 2 and 3 had good scores with net cell kills. Fil: Di Chenna, Pablo Hector. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina Fil: Benedetti Doctorovich, Violeta. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica; Argentina Fil: Garland, María T.. Universidad de Chile; Chile Fil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina |
description |
A regio- and stereospecific synthesis of monoarylimino o-quinones derived from β-lapachone (1) was achieved by treatment of the quinone with a slight excess of an arylamine in the presence of an excess of triethylamine/titanium tetrachloride 4:1. Imine formation occurred exclusively at position 6, giving the Z diastereomer, as determined by single-crystal X-ray analysis. In vitro tests for cytotoxicity in 55 human cancer cell cultures showed a substantial loss in activity for the p-nitrophenylimine (5), whereas the phenylimine (2), p-methylphenylimine (3), and p-methoxyphenylimine (4) retained (or bettered) most of the cytotoxicity and selectivity of the parent quinone. Preliminary in vivo testing in hollow fiber assays against a standard panel of 12 human tumor cell lines showed that although β-lapachone failed, compounds 2 and 3 had good scores with net cell kills. |
publishDate |
2001 |
dc.date.none.fl_str_mv |
2001-07 |
dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
format |
article |
status_str |
publishedVersion |
dc.identifier.none.fl_str_mv |
http://hdl.handle.net/11336/86463 Di Chenna, Pablo Hector; Benedetti Doctorovich, Violeta; Baggio, Ricardo Fortunato; Garland, María T.; Burton, Gerardo; Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone; American Chemical Society; Journal of Medicinal Chemistry; 44; 15; 7-2001; 2486-2489 0022-2623 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/86463 |
identifier_str_mv |
Di Chenna, Pablo Hector; Benedetti Doctorovich, Violeta; Baggio, Ricardo Fortunato; Garland, María T.; Burton, Gerardo; Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone; American Chemical Society; Journal of Medicinal Chemistry; 44; 15; 7-2001; 2486-2489 0022-2623 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jm010050u info:eu-repo/semantics/altIdentifier/doi/10.1021/jm010050u |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
American Chemical Society |
publisher.none.fl_str_mv |
American Chemical Society |
dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
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CONICET Digital (CONICET) |
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CONICET Digital (CONICET) |
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Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.name.fl_str_mv |
CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.mail.fl_str_mv |
dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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1844613843489128448 |
score |
13.070432 |