Synthesis and antibacterial activity of novel coumarinyl azo-chalcones

Coumarinyl azo-chalcone is one of the coumarin derivatives containing moiety of chalcone. This coumarinyl azo-chalcones were prepared by introduction of substituents (N(CH2CH3)2, OH, Br and OCH3) on coumarin ring. The coumarinyl azo-chalcones (122-126) were synthesised by Claisen-Schmidt condensatio...

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Main Author:	Hassan, Muhammad Aizam
Format:	Thesis
Language:	English
Published:	2016
Subjects:	QD Chemistry
Online Access:	http://eprints.utm.my/id/eprint/78235/1/MuhammadAizamHassanMFS2016.pdf
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spelling	my-utm-ep.782352018-07-30T08:51:31Z Synthesis and antibacterial activity of novel coumarinyl azo-chalcones 2016-02 Hassan, Muhammad Aizam QD Chemistry Coumarinyl azo-chalcone is one of the coumarin derivatives containing moiety of chalcone. This coumarinyl azo-chalcones were prepared by introduction of substituents (N(CH2CH3)2, OH, Br and OCH3) on coumarin ring. The coumarinyl azo-chalcones (122-126) were synthesised by Claisen-Schmidt condensation reaction of coumarin and benzaldehydes derivatives. The coumarin precursors have been prepared through Knoevenagel Condensation reaction yielded 3-acetyl-7-(diethylamino)coumarin (111), 3-acetyl-7-hydroxycoumarin (112), 3-acetyl-6-bromocoumarin (113) and 3-acetyl-7-methoxycoumarin (114). Meanwhile, benzaldehydes derivatives were prepared by coupling reaction of azo compound under cold condition, afforded 2-hydroxy-5-((4'-nitrophenyl)diazenyl)benzaldehyde (118), 2-hydroxy-5-((4'-chlorophenyl)diazenyl)benzaldehyde (119), and 2-hydroxy-5-((4'-methylphenyl)diazenyl)benzaldehyde (120). Five coumarinyl azo-chalcones were synthesised and identified as 3-((2E)-(3-(2'-hydroxy-5'-((4"-nitrophenyl)diazenyl)phenyl)acryloyl)-6-bromo-2H-chromen-2-one (122), 3-((2E)-(3-(2'-hydroxy-5'-((4"-chlorophenyl)diazenyl)phenyl)acryloyl)-6-bromo-2H-chrom-en-2-one (123), 3-((2E)-(3-(2'-hydroxy-5'-((4"-methylphenyl)diazenyl)-phenyl)acryloyl)-6-bromo-2H-chrom-en-2-one (124), 3-((2E)-(3-(2'-hydroxy-5'-((4"-chlorophenyl)diazenyl)phenyl)acryloyl)-7-methoxy-2H-chromen-2-one (125), and 3-((2E)-(3-(2'-hydroxy-5'-((4"-methylphenyl)diazenyl)phenyl)acryloyl)-7-methoxy-2H-chromen-2-one (126). The compounds obtained were characterized by infrared and nuclear magnetic resonance (1D and 2D NMR) spectroscopy. All coumarinyl azo-chalcones (122-126) were tested for the antibacterial activity against Gram-positive and Gram-negative bacteria. Coumarinyl azo-chalcone (124) showed moderate activity towards all Gram-positive and Gram-negative bacteria. 2016-02 Thesis http://eprints.utm.my/id/eprint/78235/ http://eprints.utm.my/id/eprint/78235/1/MuhammadAizamHassanMFS2016.pdf application/pdf en public http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:94244 masters Universiti Teknologi Malaysia, Faculty of Science Faculty of Science
institution	Universiti Teknologi Malaysia
collection	UTM Institutional Repository
language	English
topic	QD Chemistry
spellingShingle	QD Chemistry Hassan, Muhammad Aizam Synthesis and antibacterial activity of novel coumarinyl azo-chalcones
description	Coumarinyl azo-chalcone is one of the coumarin derivatives containing moiety of chalcone. This coumarinyl azo-chalcones were prepared by introduction of substituents (N(CH2CH3)2, OH, Br and OCH3) on coumarin ring. The coumarinyl azo-chalcones (122-126) were synthesised by Claisen-Schmidt condensation reaction of coumarin and benzaldehydes derivatives. The coumarin precursors have been prepared through Knoevenagel Condensation reaction yielded 3-acetyl-7-(diethylamino)coumarin (111), 3-acetyl-7-hydroxycoumarin (112), 3-acetyl-6-bromocoumarin (113) and 3-acetyl-7-methoxycoumarin (114). Meanwhile, benzaldehydes derivatives were prepared by coupling reaction of azo compound under cold condition, afforded 2-hydroxy-5-((4'-nitrophenyl)diazenyl)benzaldehyde (118), 2-hydroxy-5-((4'-chlorophenyl)diazenyl)benzaldehyde (119), and 2-hydroxy-5-((4'-methylphenyl)diazenyl)benzaldehyde (120). Five coumarinyl azo-chalcones were synthesised and identified as 3-((2E)-(3-(2'-hydroxy-5'-((4"-nitrophenyl)diazenyl)phenyl)acryloyl)-6-bromo-2H-chromen-2-one (122), 3-((2E)-(3-(2'-hydroxy-5'-((4"-chlorophenyl)diazenyl)phenyl)acryloyl)-6-bromo-2H-chrom-en-2-one (123), 3-((2E)-(3-(2'-hydroxy-5'-((4"-methylphenyl)diazenyl)-phenyl)acryloyl)-6-bromo-2H-chrom-en-2-one (124), 3-((2E)-(3-(2'-hydroxy-5'-((4"-chlorophenyl)diazenyl)phenyl)acryloyl)-7-methoxy-2H-chromen-2-one (125), and 3-((2E)-(3-(2'-hydroxy-5'-((4"-methylphenyl)diazenyl)phenyl)acryloyl)-7-methoxy-2H-chromen-2-one (126). The compounds obtained were characterized by infrared and nuclear magnetic resonance (1D and 2D NMR) spectroscopy. All coumarinyl azo-chalcones (122-126) were tested for the antibacterial activity against Gram-positive and Gram-negative bacteria. Coumarinyl azo-chalcone (124) showed moderate activity towards all Gram-positive and Gram-negative bacteria.
format	Thesis
qualification_level	Master's degree
author	Hassan, Muhammad Aizam
author_facet	Hassan, Muhammad Aizam
author_sort	Hassan, Muhammad Aizam
title	Synthesis and antibacterial activity of novel coumarinyl azo-chalcones
title_short	Synthesis and antibacterial activity of novel coumarinyl azo-chalcones
title_full	Synthesis and antibacterial activity of novel coumarinyl azo-chalcones
title_fullStr	Synthesis and antibacterial activity of novel coumarinyl azo-chalcones
title_full_unstemmed	Synthesis and antibacterial activity of novel coumarinyl azo-chalcones
title_sort	synthesis and antibacterial activity of novel coumarinyl azo-chalcones
granting_institution	Universiti Teknologi Malaysia, Faculty of Science
granting_department	Faculty of Science
publishDate	2016
url	http://eprints.utm.my/id/eprint/78235/1/MuhammadAizamHassanMFS2016.pdf
_version_	1747817940142522368

Synthesis and antibacterial activity of novel coumarinyl azo-chalcones

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