SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY

Nine (8-Hydroxyquinolin-5-yl)-arylpropenones were synthesized and their structures demonstrated by IR and NMRspectroscopy. These molecules showed transconfiguration and strong intramolecular hydrogen bonding; in the IR spectra of 5-formyl-8-hydroxyquinoline, 5-acetyl-8-hydroxyquinoline, 1-(8-hydroxy...

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Autores principales:	MARRUGO-GONZÁLEZ,ALONSO J, ORLOV,VALERIE D, FERNANDEZ-MAESTRE,ROBERTO
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2012
Materias:	8-hydroxyquinoline chalcones bromination antifungal activity
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072012000300019
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spelling	oai:scielo:S0717-970720120003000192019-02-19SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITYMARRUGO-GONZÁLEZ,ALONSO JORLOV,VALERIE DFERNANDEZ-MAESTRE,ROBERTO 8-hydroxyquinoline chalcones bromination antifungal activity Nine (8-Hydroxyquinolin-5-yl)-arylpropenones were synthesized and their structures demonstrated by IR and NMRspectroscopy. These molecules showed transconfiguration and strong intramolecular hydrogen bonding; in the IR spectra of 5-formyl-8-hydroxyquinoline, 5-acetyl-8-hydroxyquinoline, 1-(8-hydroxyquinolin-5-yl)-3-phenylprop-2-en-1-one and 3-(8-hydroxyquinolin-5-yl)-1-phenylprop-2-en-1-one in CHCl3, besides the known intermolecular hydrogen band (~3180 cm-1), we identified the intramolecular hydrogen band OH-N (3460 cm-1); the hydrogen bond peaks shifted to low frequency in proton-donor solutions such as phenol and acetic acid (with respect to 8-hydroxyquinoline) and the bonds were broken in trifluoroacetic acid solutions, due to OH protonation; the apolar solvent CCl4 and electrophilic substituents in position 5 in the quinoline ring, limited the formation of the intermolecular hydrogen bonds and, therefore, shifted the ~3460 cm-1 intramolecular hydrogen band to lower frequencies and made it stronger and sharper. The bromination of 3-(8-hydroxyquinolin-5-yl)-1-(4-tolyl) prop-2-en-1-one occurred on the activated quinoline fragment, producing monobromo and tetrabromo derivatives, instead of bromination on the aliphatic double bond. Three chalcones tested showed strong antifungal activity in vitro.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.57 n.3 20122012-01-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072012000300019en10.4067/S0717-97072012000300019
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	8-hydroxyquinoline chalcones bromination antifungal activity
spellingShingle	8-hydroxyquinoline chalcones bromination antifungal activity MARRUGO-GONZÁLEZ,ALONSO J ORLOV,VALERIE D FERNANDEZ-MAESTRE,ROBERTO SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY
description	Nine (8-Hydroxyquinolin-5-yl)-arylpropenones were synthesized and their structures demonstrated by IR and NMRspectroscopy. These molecules showed transconfiguration and strong intramolecular hydrogen bonding; in the IR spectra of 5-formyl-8-hydroxyquinoline, 5-acetyl-8-hydroxyquinoline, 1-(8-hydroxyquinolin-5-yl)-3-phenylprop-2-en-1-one and 3-(8-hydroxyquinolin-5-yl)-1-phenylprop-2-en-1-one in CHCl3, besides the known intermolecular hydrogen band (~3180 cm-1), we identified the intramolecular hydrogen band OH-N (3460 cm-1); the hydrogen bond peaks shifted to low frequency in proton-donor solutions such as phenol and acetic acid (with respect to 8-hydroxyquinoline) and the bonds were broken in trifluoroacetic acid solutions, due to OH protonation; the apolar solvent CCl4 and electrophilic substituents in position 5 in the quinoline ring, limited the formation of the intermolecular hydrogen bonds and, therefore, shifted the ~3460 cm-1 intramolecular hydrogen band to lower frequencies and made it stronger and sharper. The bromination of 3-(8-hydroxyquinolin-5-yl)-1-(4-tolyl) prop-2-en-1-one occurred on the activated quinoline fragment, producing monobromo and tetrabromo derivatives, instead of bromination on the aliphatic double bond. Three chalcones tested showed strong antifungal activity in vitro.
author	MARRUGO-GONZÁLEZ,ALONSO J ORLOV,VALERIE D FERNANDEZ-MAESTRE,ROBERTO
author_facet	MARRUGO-GONZÁLEZ,ALONSO J ORLOV,VALERIE D FERNANDEZ-MAESTRE,ROBERTO
author_sort	MARRUGO-GONZÁLEZ,ALONSO J
title	SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY
title_short	SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY
title_full	SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY
title_fullStr	SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY
title_full_unstemmed	SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY
title_sort	synthesis of 8-hydroxyquinoline chalcones: trans configuration, intramolecular hydrogen bonds, bromination, and antifungal activity
publisher	Sociedad Chilena de Química
publishDate	2012
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072012000300019
work_keys_str_mv	AT marrugogonzalezalonsoj synthesisof8hydroxyquinolinechalconestransconfigurationintramolecularhydrogenbondsbrominationandantifungalactivity AT orlovvaleried synthesisof8hydroxyquinolinechalconestransconfigurationintramolecularhydrogenbondsbrominationandantifungalactivity AT fernandezmaestreroberto synthesisof8hydroxyquinolinechalconestransconfigurationintramolecularhydrogenbondsbrominationandantifungalactivity
_version_	1718445471025856512

SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY

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