Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone

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, g...

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Autores principales:	Di Chenna, Pablo Héctor, Benedetti, Miryan Olga Violeta, Baggio, Ricardo F., Burton, Gerardo
Publicado:	2001
Materias:	2,2 dimethyl 6 (4 methylphenylimino) 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one 2,2 dimethyl 6 phenylimino 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one antineoplastic agent beta lapachone derivative unclassified drug antineoplastic activity article cancer cell culture cancer inhibition controlled study cytotoxicity drug mechanism drug structure drug synthesis human human cell Antineoplastic Agents Crystallography, X-Ray Drug Screening Assays, Antitumor Humans Imines Magnetic Resonance Spectroscopy Naphthalenes Naphthoquinones Pyrans Stereoisomerism Structure-Activity Relationship Tumor Cells, Cultured
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222623_v44_n15_p2486_DiChenna http://hdl.handle.net/20.500.12110/paper_00222623_v44_n15_p2486_DiChenna
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00222623_v44_n15_p2486_DiChenna
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spelling	paper:paper_00222623_v44_n15_p2486_DiChenna2023-06-08T14:48:37Z Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone Di Chenna, Pablo Héctor Benedetti, Miryan Olga Violeta Baggio, Ricardo F. Burton, Gerardo 2,2 dimethyl 6 (4 methylphenylimino) 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one 2,2 dimethyl 6 phenylimino 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one antineoplastic agent beta lapachone derivative unclassified drug antineoplastic activity article cancer cell culture cancer inhibition controlled study cytotoxicity drug mechanism drug structure drug synthesis human human cell Antineoplastic Agents Crystallography, X-Ray Drug Screening Assays, Antitumor Humans Imines Magnetic Resonance Spectroscopy Naphthalenes Naphthoquinones Pyrans Stereoisomerism Structure-Activity Relationship Tumor Cells, Cultured 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, P.H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Benedetti-Doctorovich, V. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Baggio, R.F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2001 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222623_v44_n15_p2486_DiChenna http://hdl.handle.net/20.500.12110/paper_00222623_v44_n15_p2486_DiChenna
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	2,2 dimethyl 6 (4 methylphenylimino) 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one 2,2 dimethyl 6 phenylimino 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one antineoplastic agent beta lapachone derivative unclassified drug antineoplastic activity article cancer cell culture cancer inhibition controlled study cytotoxicity drug mechanism drug structure drug synthesis human human cell Antineoplastic Agents Crystallography, X-Ray Drug Screening Assays, Antitumor Humans Imines Magnetic Resonance Spectroscopy Naphthalenes Naphthoquinones Pyrans Stereoisomerism Structure-Activity Relationship Tumor Cells, Cultured
spellingShingle	2,2 dimethyl 6 (4 methylphenylimino) 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one 2,2 dimethyl 6 phenylimino 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one antineoplastic agent beta lapachone derivative unclassified drug antineoplastic activity article cancer cell culture cancer inhibition controlled study cytotoxicity drug mechanism drug structure drug synthesis human human cell Antineoplastic Agents Crystallography, X-Ray Drug Screening Assays, Antitumor Humans Imines Magnetic Resonance Spectroscopy Naphthalenes Naphthoquinones Pyrans Stereoisomerism Structure-Activity Relationship Tumor Cells, Cultured Di Chenna, Pablo Héctor Benedetti, Miryan Olga Violeta Baggio, Ricardo F. Burton, Gerardo Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone
topic_facet	2,2 dimethyl 6 (4 methylphenylimino) 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one 2,2 dimethyl 6 phenylimino 3,4,5,6 tetrahydro 2h naphtho[1,2 b]oxin 5 one antineoplastic agent beta lapachone derivative unclassified drug antineoplastic activity article cancer cell culture cancer inhibition controlled study cytotoxicity drug mechanism drug structure drug synthesis human human cell Antineoplastic Agents Crystallography, X-Ray Drug Screening Assays, Antitumor Humans Imines Magnetic Resonance Spectroscopy Naphthalenes Naphthoquinones Pyrans Stereoisomerism Structure-Activity Relationship Tumor Cells, Cultured
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.
author	Di Chenna, Pablo Héctor Benedetti, Miryan Olga Violeta Baggio, Ricardo F. Burton, Gerardo
author_facet	Di Chenna, Pablo Héctor Benedetti, Miryan Olga Violeta Baggio, Ricardo F. Burton, Gerardo
author_sort	Di Chenna, Pablo Héctor
title	Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone
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
publishDate	2001
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222623_v44_n15_p2486_DiChenna http://hdl.handle.net/20.500.12110/paper_00222623_v44_n15_p2486_DiChenna
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_version_	1768544717875707904

Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of β-lapachone

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