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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| Format: | Thesis |
| Language: | English |
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2016
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| Online Access: | http://eprints.utm.my/78235/1/MuhammadAizamHassanMFS2016.pdf |
| _version_ | 1796862812206661632 |
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| author | Hassan, Muhammad Aizam |
| author_facet | Hassan, Muhammad Aizam |
| author_sort | Hassan, Muhammad Aizam |
| collection | ePrints |
| 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. |
| first_indexed | 2024-03-05T20:17:15Z |
| format | Thesis |
| id | utm.eprints-78235 |
| institution | Universiti Teknologi Malaysia - ePrints |
| language | English |
| last_indexed | 2024-03-05T20:17:15Z |
| publishDate | 2016 |
| record_format | dspace |
| spelling | utm.eprints-782352018-07-30T08:51:31Z http://eprints.utm.my/78235/ Synthesis and antibacterial activity of novel coumarinyl azo-chalcones 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 NonPeerReviewed application/pdf en http://eprints.utm.my/78235/1/MuhammadAizamHassanMFS2016.pdf Hassan, Muhammad Aizam (2016) Synthesis and antibacterial activity of novel coumarinyl azo-chalcones. Masters thesis, Universiti Teknologi Malaysia, Faculty of Science. http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:94244 |
| spellingShingle | QD Chemistry Hassan, Muhammad Aizam Synthesis and antibacterial activity of novel coumarinyl azo-chalcones |
| title | 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_short | Synthesis and antibacterial activity of novel coumarinyl azo-chalcones |
| title_sort | synthesis and antibacterial activity of novel coumarinyl azo chalcones |
| topic | QD Chemistry |
| url | http://eprints.utm.my/78235/1/MuhammadAizamHassanMFS2016.pdf |
| work_keys_str_mv | AT hassanmuhammadaizam synthesisandantibacterialactivityofnovelcoumarinylazochalcones |