4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate
4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate (<b>1</b>) was obtained in a good yield by the reaction of 2-methylcinnamic acid, 4-methoxyphenethyl alcohol, 2-methyl-6-nitrobenzoic anhydride, 4-dimethylaminopyridine, and triethylamine at room temperature...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-12-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2022/4/M1519 |
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| author | Mardi Santoso Egar Pamela Ersya Yanu Ramadhani Yan Alamanda Ilfahmi Nur Pasca Aijijiyah Adi Setyo Purnomo Surya Rosa Putra |
| author_facet | Mardi Santoso Egar Pamela Ersya Yanu Ramadhani Yan Alamanda Ilfahmi Nur Pasca Aijijiyah Adi Setyo Purnomo Surya Rosa Putra |
| author_sort | Mardi Santoso |
| collection | DOAJ |
| description | 4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate (<b>1</b>) was obtained in a good yield by the reaction of 2-methylcinnamic acid, 4-methoxyphenethyl alcohol, 2-methyl-6-nitrobenzoic anhydride, 4-dimethylaminopyridine, and triethylamine at room temperature for 40 min. The structure of 4-methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate (<b>1</b>) was established by FTIR, NMR, and the high resolution of mass spectroscopies. 4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate (<b>1</b>) showed higher α-glucosidase inhibition activity than standard drug acarbose. The molecular docking study exhibited that the title compound <b>1</b> had a good affinity for α-glucosidase (PDB ID: 3W37) and formed some interactions with the α-glucosidase active site residue. |
| first_indexed | 2024-03-09T16:02:56Z |
| format | Article |
| id | doaj.art-17fbfdfb4c874d96a3c1cf54dfbabfc8 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T16:02:56Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-17fbfdfb4c874d96a3c1cf54dfbabfc82023-11-24T16:54:40ZengMDPI AGMolbank1422-85992022-12-0120224M151910.3390/M15194-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylateMardi Santoso0Egar Pamela1Ersya Yanu Ramadhani2Yan Alamanda Ilfahmi3Nur Pasca Aijijiyah4Adi Setyo Purnomo5Surya Rosa Putra6Department of Chemistry, Faculty of Science and Analytical Data, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, IndonesiaDepartment of Chemistry, Faculty of Science and Analytical Data, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, IndonesiaDepartment of Chemistry, Faculty of Science and Analytical Data, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, IndonesiaDepartment of Chemistry, Faculty of Science and Analytical Data, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, IndonesiaDepartment of Chemistry, Faculty of Science and Analytical Data, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, IndonesiaDepartment of Chemistry, Faculty of Science and Analytical Data, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, IndonesiaDepartment of Chemistry, Faculty of Science and Analytical Data, Institut Teknologi Sepuluh Nopember, Kampus ITS Sukolilo, Surabaya 60111, Indonesia4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate (<b>1</b>) was obtained in a good yield by the reaction of 2-methylcinnamic acid, 4-methoxyphenethyl alcohol, 2-methyl-6-nitrobenzoic anhydride, 4-dimethylaminopyridine, and triethylamine at room temperature for 40 min. The structure of 4-methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate (<b>1</b>) was established by FTIR, NMR, and the high resolution of mass spectroscopies. 4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate (<b>1</b>) showed higher α-glucosidase inhibition activity than standard drug acarbose. The molecular docking study exhibited that the title compound <b>1</b> had a good affinity for α-glucosidase (PDB ID: 3W37) and formed some interactions with the α-glucosidase active site residue.https://www.mdpi.com/1422-8599/2022/4/M1519cinnamic acid estersynthesisα-glucosidase inhibitionmolecular dockingdisease |
| spellingShingle | Mardi Santoso Egar Pamela Ersya Yanu Ramadhani Yan Alamanda Ilfahmi Nur Pasca Aijijiyah Adi Setyo Purnomo Surya Rosa Putra 4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate Molbank cinnamic acid ester synthesis α-glucosidase inhibition molecular docking disease |
| title | 4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate |
| title_full | 4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate |
| title_fullStr | 4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate |
| title_full_unstemmed | 4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate |
| title_short | 4-Methoxyphenethyl (<i>E</i>)-3-(<i>o</i>-tolyl)acrylate |
| title_sort | 4 methoxyphenethyl i e i 3 i o i tolyl acrylate |
| topic | cinnamic acid ester synthesis α-glucosidase inhibition molecular docking disease |
| url | https://www.mdpi.com/1422-8599/2022/4/M1519 |
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