2,9-Dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-one
The new 2,9-dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-one was successfully prepared through the three-component iodine-catalyzed reaction of <i>n</i>-butyl vinyl ether with the new 8-amino-2-methyl-4<i>H</i>-chromeno[3,4-<i...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2023/1/M1591 |
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| author | Evangelia-Eirini N. Vlachou Thomas D. Balalas Dimitra J. Hadjipavlou-Litina Konstantinos E. Litinas Matina Douka |
| author_facet | Evangelia-Eirini N. Vlachou Thomas D. Balalas Dimitra J. Hadjipavlou-Litina Konstantinos E. Litinas Matina Douka |
| author_sort | Evangelia-Eirini N. Vlachou |
| collection | DOAJ |
| description | The new 2,9-dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-one was successfully prepared through the three-component iodine-catalyzed reaction of <i>n</i>-butyl vinyl ether with the new 8-amino-2-methyl-4<i>H</i>-chromeno[3,4-<i>d</i>]oxazol-4-one. The latter was prepared by the reduction of 2-methyl-8-nitro-4<i>H</i>-chromeno[3,4-<i>d</i>]oxazol-4-one with Pd/C in a hydrogen atmosphere. The above nitro compound was synthesized by the condensation of <i>N</i>-(4-hydroxy-6-nitro-2-oxo-2<i>H</i>-chromen-3-yl)acetamide with P<sub>2</sub>O<sub>5</sub> under microwave irradiation. The above acetamide derivative was prepared during the nitration of 2-methyl-4<i>H</i>-chromeno[3,4-<i>d</i>]oxazol-4-one with H<sub>2</sub>SO<sub>4</sub> and KNO<sub>3</sub>. The structure of the newly synthesized compounds was confirmed by FT-IR, LC-MS, <sup>1</sup>H-NMR, and <sup>13</sup>C-NMR analyses. Preliminary biological tests show significant anti-lipid peroxidation activity for the title compound and the other synthesized new intermediates, as well as interesting soybean lipoxygenase inhibition for acetamide <b>2</b> (IC<sub>50</sub> 55 μM) and nitro-compound <b>3</b> (IC<sub>50</sub> 27 μM). |
| first_indexed | 2024-03-11T06:08:05Z |
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| id | doaj.art-306e5a2cad48427ba621293e3a757aec |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-11T06:08:05Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-306e5a2cad48427ba621293e3a757aec2023-11-17T12:49:51ZengMDPI AGMolbank1422-85992023-02-0120231M159110.3390/M15912,9-Dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-oneEvangelia-Eirini N. Vlachou0Thomas D. Balalas1Dimitra J. Hadjipavlou-Litina2Konstantinos E. Litinas3Matina Douka4Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, GreeceLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, GreeceDepartment of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, 54124 Thessaloniki, GreeceLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, GreeceLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, GreeceThe new 2,9-dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-one was successfully prepared through the three-component iodine-catalyzed reaction of <i>n</i>-butyl vinyl ether with the new 8-amino-2-methyl-4<i>H</i>-chromeno[3,4-<i>d</i>]oxazol-4-one. The latter was prepared by the reduction of 2-methyl-8-nitro-4<i>H</i>-chromeno[3,4-<i>d</i>]oxazol-4-one with Pd/C in a hydrogen atmosphere. The above nitro compound was synthesized by the condensation of <i>N</i>-(4-hydroxy-6-nitro-2-oxo-2<i>H</i>-chromen-3-yl)acetamide with P<sub>2</sub>O<sub>5</sub> under microwave irradiation. The above acetamide derivative was prepared during the nitration of 2-methyl-4<i>H</i>-chromeno[3,4-<i>d</i>]oxazol-4-one with H<sub>2</sub>SO<sub>4</sub> and KNO<sub>3</sub>. The structure of the newly synthesized compounds was confirmed by FT-IR, LC-MS, <sup>1</sup>H-NMR, and <sup>13</sup>C-NMR analyses. Preliminary biological tests show significant anti-lipid peroxidation activity for the title compound and the other synthesized new intermediates, as well as interesting soybean lipoxygenase inhibition for acetamide <b>2</b> (IC<sub>50</sub> 55 μM) and nitro-compound <b>3</b> (IC<sub>50</sub> 27 μM).https://www.mdpi.com/1422-8599/2023/1/M1591I<sub>2</sub>-catalysisfused pyridocoumarinfused oxazolocoumarinamino-substituted fused oxazolocoumarinmicrowave irradiation |
| spellingShingle | Evangelia-Eirini N. Vlachou Thomas D. Balalas Dimitra J. Hadjipavlou-Litina Konstantinos E. Litinas Matina Douka 2,9-Dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-one Molbank I<sub>2</sub>-catalysis fused pyridocoumarin fused oxazolocoumarin amino-substituted fused oxazolocoumarin microwave irradiation |
| title | 2,9-Dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-one |
| title_full | 2,9-Dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-one |
| title_fullStr | 2,9-Dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-one |
| title_full_unstemmed | 2,9-Dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-one |
| title_short | 2,9-Dimethyl-4<i>H</i>-oxazolo[5’,4’:4,5]pyrano[3,2-<i>f</i>]quinolin-4-one |
| title_sort | 2 9 dimethyl 4 i h i oxazolo 5 4 4 5 pyrano 3 2 i f i quinolin 4 one |
| topic | I<sub>2</sub>-catalysis fused pyridocoumarin fused oxazolocoumarin amino-substituted fused oxazolocoumarin microwave irradiation |
| url | https://www.mdpi.com/1422-8599/2023/1/M1591 |
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