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
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/86463
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling 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 Técnicas2025-11-12T09:46:20Zoai: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:34982025-11-12 09:46:20.863CONICET 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
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str 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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score 13.3211565

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