Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol

A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydr...

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Autores principales:	Bonifazi, Evelyn Lucía, Burton, Gerardo
Publicado:	2010
Materias:	Antiproliferative Lapachol Lapachone Naphthoquinone 1,4 naphthoquinone derivative 2,3 dihydro 5 hydroxy 2 (prop 1 en 2 yl)naphtho[2,3 b]furan 4,9 dione 2,5 dihydroxy 3 (3 methylbut 2 enyl)naphthalene 1,4 dione 5 hydroxylapachol juglone lapachol unclassified drug article cancer cell culture drug activity drug structure drug synthesis human human cell lipophilicity prenylation structure activity relation Antineoplastic Agents, Phytogenic Cell Line, Tumor Drug Screening Assays, Antitumor Humans Indicators and Reagents Lipids Magnetic Resonance Spectroscopy Naphthoquinones Prenylation Structure-Activity Relationship
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v18_n7_p2621_Bonifazi http://hdl.handle.net/20.500.12110/paper_09680896_v18_n7_p2621_Bonifazi
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_09680896_v18_n7_p2621_Bonifazi
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spelling	paper:paper_09680896_v18_n7_p2621_Bonifazi2023-06-08T15:58:53Z Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol Bonifazi, Evelyn Lucía Burton, Gerardo Antiproliferative Lapachol Lapachone Naphthoquinone 1,4 naphthoquinone derivative 2,3 dihydro 5 hydroxy 2 (prop 1 en 2 yl)naphtho[2,3 b]furan 4,9 dione 2,5 dihydroxy 3 (3 methylbut 2 enyl)naphthalene 1,4 dione 5 hydroxylapachol juglone lapachol unclassified drug article cancer cell culture drug activity drug structure drug synthesis human human cell lipophilicity prenylation structure activity relation Antineoplastic Agents, Phytogenic Cell Line, Tumor Drug Screening Assays, Antitumor Humans Indicators and Reagents Lipids Magnetic Resonance Spectroscopy Naphthoquinones Prenylation Structure-Activity Relationship A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents with GI50 values of 0.42-8.1 and 0.80-2.2 μM, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity. © 2010 Elsevier Ltd. All rights reserved. Fil:Bonifazi, E.L. 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. 2010 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v18_n7_p2621_Bonifazi http://hdl.handle.net/20.500.12110/paper_09680896_v18_n7_p2621_Bonifazi
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Antiproliferative Lapachol Lapachone Naphthoquinone 1,4 naphthoquinone derivative 2,3 dihydro 5 hydroxy 2 (prop 1 en 2 yl)naphtho[2,3 b]furan 4,9 dione 2,5 dihydroxy 3 (3 methylbut 2 enyl)naphthalene 1,4 dione 5 hydroxylapachol juglone lapachol unclassified drug article cancer cell culture drug activity drug structure drug synthesis human human cell lipophilicity prenylation structure activity relation Antineoplastic Agents, Phytogenic Cell Line, Tumor Drug Screening Assays, Antitumor Humans Indicators and Reagents Lipids Magnetic Resonance Spectroscopy Naphthoquinones Prenylation Structure-Activity Relationship
spellingShingle	Antiproliferative Lapachol Lapachone Naphthoquinone 1,4 naphthoquinone derivative 2,3 dihydro 5 hydroxy 2 (prop 1 en 2 yl)naphtho[2,3 b]furan 4,9 dione 2,5 dihydroxy 3 (3 methylbut 2 enyl)naphthalene 1,4 dione 5 hydroxylapachol juglone lapachol unclassified drug article cancer cell culture drug activity drug structure drug synthesis human human cell lipophilicity prenylation structure activity relation Antineoplastic Agents, Phytogenic Cell Line, Tumor Drug Screening Assays, Antitumor Humans Indicators and Reagents Lipids Magnetic Resonance Spectroscopy Naphthoquinones Prenylation Structure-Activity Relationship Bonifazi, Evelyn Lucía Burton, Gerardo Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
topic_facet	Antiproliferative Lapachol Lapachone Naphthoquinone 1,4 naphthoquinone derivative 2,3 dihydro 5 hydroxy 2 (prop 1 en 2 yl)naphtho[2,3 b]furan 4,9 dione 2,5 dihydroxy 3 (3 methylbut 2 enyl)naphthalene 1,4 dione 5 hydroxylapachol juglone lapachol unclassified drug article cancer cell culture drug activity drug structure drug synthesis human human cell lipophilicity prenylation structure activity relation Antineoplastic Agents, Phytogenic Cell Line, Tumor Drug Screening Assays, Antitumor Humans Indicators and Reagents Lipids Magnetic Resonance Spectroscopy Naphthoquinones Prenylation Structure-Activity Relationship
description	A series of 5-hydroxy-1,4-naphthoquinones analogues was synthesized from juglone (6) and their antiproliferative activity against a representative panel of six human solid tumor cell lines has been investigated. The 2,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione (4) and 2,3-dihydro-5-hydroxy-2-(prop-1-en-2-yl)naphtho[2,3-b]furan-4,9-dione (27) were the most potent antiproliferative agents with GI50 values of 0.42-8.1 and 0.80-2.2 μM, respectively. The results provide insight into the correlation between some structural properties of 5-hydroxynaphthoquinones and their antiproliferative activity. © 2010 Elsevier Ltd. All rights reserved.
author	Bonifazi, Evelyn Lucía Burton, Gerardo
author_facet	Bonifazi, Evelyn Lucía Burton, Gerardo
author_sort	Bonifazi, Evelyn Lucía
title	Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
title_short	Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
title_full	Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
title_fullStr	Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
title_full_unstemmed	Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol
title_sort	antiproliferative activity of synthetic naphthoquinones related to lapachol. first synthesis of 5-hydroxylapachol
publishDate	2010
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v18_n7_p2621_Bonifazi http://hdl.handle.net/20.500.12110/paper_09680896_v18_n7_p2621_Bonifazi
work_keys_str_mv	AT bonifazievelynlucia antiproliferativeactivityofsyntheticnaphthoquinonesrelatedtolapacholfirstsynthesisof5hydroxylapachol AT burtongerardo antiproliferativeactivityofsyntheticnaphthoquinonesrelatedtolapacholfirstsynthesisof5hydroxylapachol
_version_	1768542701287899136

Antiproliferative activity of synthetic naphthoquinones related to lapachol. First synthesis of 5-hydroxylapachol

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