Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone Derivatives
In this research, the synthesis of new substituted oxazolone derivatives is described via Erlenmeyer synthesis of N-acyl amino acid. Firstly, the azo derivative 1 was prepared by coupling the diazonium salt of 3-amino-4-methoxybenzoic acid with 4,5-dichloroimidazole in sodium hydroxide solution. Ben...
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| Format: | Article |
| Language: | English |
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Department of Chemistry, Universitas Gadjah Mada
2023-10-01
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| Series: | Indonesian Journal of Chemistry |
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| Online Access: | https://jurnal.ugm.ac.id/ijc/article/view/83052 |
| _version_ | 1797657966824914944 |
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| author | Lina Saadi Shaimaa Adnan |
| author_facet | Lina Saadi Shaimaa Adnan |
| author_sort | Lina Saadi |
| collection | DOAJ |
| description | In this research, the synthesis of new substituted oxazolone derivatives is described via Erlenmeyer synthesis of N-acyl amino acid. Firstly, the azo derivative 1 was prepared by coupling the diazonium salt of 3-amino-4-methoxybenzoic acid with 4,5-dichloroimidazole in sodium hydroxide solution. Benzoyl chloride derivative 2, the key intermediate of the synthesis, was synthesized by the acylation of azo-carboxylic acid derivative 1 with thionyl chloride. The resulting acyl chloride derivative reacted with glycine in a basic catalyst to form a hippuric acid derivative 3. After that, oxazolone derivatives 4a–4f were prepared via the reaction of the hippuric acid derivative with various aromatic aldehydes. All new compound structures were confirmed by spectral techniques, i.e., FTIR, 1H-NMR, 13C-NMR spectroscopy, and elemental analysis. The antimicrobial activity (Staphylococcus aureus and Escherichia coli) of all new compounds was screened in vitro. The results against S. aureus and E. coli showed that most of the tested compounds have an activity ranging from moderate to low. The antioxidant activity of derivative 4a was also evaluated and showed good antioxidant activity. |
| first_indexed | 2024-03-11T17:52:13Z |
| format | Article |
| id | doaj.art-a82821d210904f4ab0ff176c42b4d55b |
| institution | Directory Open Access Journal |
| issn | 1411-9420 2460-1578 |
| language | English |
| last_indexed | 2024-03-11T17:52:13Z |
| publishDate | 2023-10-01 |
| publisher | Department of Chemistry, Universitas Gadjah Mada |
| record_format | Article |
| series | Indonesian Journal of Chemistry |
| spelling | doaj.art-a82821d210904f4ab0ff176c42b4d55b2023-10-18T00:12:06ZengDepartment of Chemistry, Universitas Gadjah MadaIndonesian Journal of Chemistry1411-94202460-15782023-10-012351463147110.22146/ijc.8305234528Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone DerivativesLina Saadi0Shaimaa Adnan1Department of Pharmaceutical Chemistry, College of Pharmacy, University of Al-Qadisiyah, Diwaniyah 58001, IraqDepartment of Chemistry, College of Education, University of Al-Qadisiyah, Diwaniyah 58001, IraqIn this research, the synthesis of new substituted oxazolone derivatives is described via Erlenmeyer synthesis of N-acyl amino acid. Firstly, the azo derivative 1 was prepared by coupling the diazonium salt of 3-amino-4-methoxybenzoic acid with 4,5-dichloroimidazole in sodium hydroxide solution. Benzoyl chloride derivative 2, the key intermediate of the synthesis, was synthesized by the acylation of azo-carboxylic acid derivative 1 with thionyl chloride. The resulting acyl chloride derivative reacted with glycine in a basic catalyst to form a hippuric acid derivative 3. After that, oxazolone derivatives 4a–4f were prepared via the reaction of the hippuric acid derivative with various aromatic aldehydes. All new compound structures were confirmed by spectral techniques, i.e., FTIR, 1H-NMR, 13C-NMR spectroscopy, and elemental analysis. The antimicrobial activity (Staphylococcus aureus and Escherichia coli) of all new compounds was screened in vitro. The results against S. aureus and E. coli showed that most of the tested compounds have an activity ranging from moderate to low. The antioxidant activity of derivative 4a was also evaluated and showed good antioxidant activity.https://jurnal.ugm.ac.id/ijc/article/view/83052antibacterialantioxidantserlenmeyer reactionglycineoxazolone |
| spellingShingle | Lina Saadi Shaimaa Adnan Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone Derivatives Indonesian Journal of Chemistry antibacterial antioxidants erlenmeyer reaction glycine oxazolone |
| title | Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone Derivatives |
| title_full | Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone Derivatives |
| title_fullStr | Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone Derivatives |
| title_full_unstemmed | Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone Derivatives |
| title_short | Synthesis, Antibacterial and Antioxidant Evaluation of 2-Substituted-4-arylidene-5(4<i>H</i>)-oxazolone Derivatives |
| title_sort | synthesis antibacterial and antioxidant evaluation of 2 substituted 4 arylidene 5 4 i h i oxazolone derivatives |
| topic | antibacterial antioxidants erlenmeyer reaction glycine oxazolone |
| url | https://jurnal.ugm.ac.id/ijc/article/view/83052 |
| work_keys_str_mv | AT linasaadi synthesisantibacterialandantioxidantevaluationof2substituted4arylidene54ihioxazolonederivatives AT shaimaaadnan synthesisantibacterialandantioxidantevaluationof2substituted4arylidene54ihioxazolonederivatives |