New Experimental Conditions for Diels–Alder and Friedel-Crafts Alquilation Reactions with Thiophene: A New Selenocyanate with Potent Activity against Cancer
The reactivity of thiophene in Diels-Alder reactions is investigated with different maleimide derivatives. In this paper, we have synthesized for the first time the Diels–Alder adducts of thiophene at room temperature and atmospheric pressure. Maleimido–thiophene adducts were promoted by AlCl<sub...
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| Format: | Article |
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MDPI AG
2022-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/3/982 |
| _version_ | 1797486001535320064 |
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| author | Gorka Calvo-Martín Daniel Plano Carmen Sanmartín |
| author_facet | Gorka Calvo-Martín Daniel Plano Carmen Sanmartín |
| author_sort | Gorka Calvo-Martín |
| collection | DOAJ |
| description | The reactivity of thiophene in Diels-Alder reactions is investigated with different maleimide derivatives. In this paper, we have synthesized for the first time the Diels–Alder adducts of thiophene at room temperature and atmospheric pressure. Maleimido–thiophene adducts were promoted by AlCl<sub>3</sub>. The effects of solvent, time, temperature and the use of different Lewis acids were studied, showing dramatic effects for solvent and Lewis acid. Furthermore, the catalysis with AlCl<sub>3</sub> is highly stereoselective, preferably providing the exo form of the adduct. Additionally, we also discovered the ability of AlCl<sub>3</sub> to catalyze the arylation of maleimides to yield 3-aryl succinimides in a straightforward manner following a Friedel–Crafts-type addition. The inclusion of a selenocyanate group contributes to the cytotoxic activity of the adduct. This derivatization (from compound <b>7</b> to compound <b>15</b>) results in an average GI<sub>50</sub> value of 1.98 µM in the DTP (NCI-60) cell panel, resulting in being especially active in renal cancer cells. |
| first_indexed | 2024-03-09T23:26:56Z |
| format | Article |
| id | doaj.art-044c6522d32b4c669268536b1bbf0905 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T23:26:56Z |
| publishDate | 2022-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-044c6522d32b4c669268536b1bbf09052023-11-23T17:15:40ZengMDPI AGMolecules1420-30492022-02-0127398210.3390/molecules27030982New Experimental Conditions for Diels–Alder and Friedel-Crafts Alquilation Reactions with Thiophene: A New Selenocyanate with Potent Activity against CancerGorka Calvo-Martín0Daniel Plano1Carmen Sanmartín2Departamento de Tecnología y Química Farmacéuticas, Facultad de Farmacia y Nutrición, Universidad de Navarra, Irunlarrea 1, E-31008 Pamplona, SpainDepartamento de Tecnología y Química Farmacéuticas, Facultad de Farmacia y Nutrición, Universidad de Navarra, Irunlarrea 1, E-31008 Pamplona, SpainDepartamento de Tecnología y Química Farmacéuticas, Facultad de Farmacia y Nutrición, Universidad de Navarra, Irunlarrea 1, E-31008 Pamplona, SpainThe reactivity of thiophene in Diels-Alder reactions is investigated with different maleimide derivatives. In this paper, we have synthesized for the first time the Diels–Alder adducts of thiophene at room temperature and atmospheric pressure. Maleimido–thiophene adducts were promoted by AlCl<sub>3</sub>. The effects of solvent, time, temperature and the use of different Lewis acids were studied, showing dramatic effects for solvent and Lewis acid. Furthermore, the catalysis with AlCl<sub>3</sub> is highly stereoselective, preferably providing the exo form of the adduct. Additionally, we also discovered the ability of AlCl<sub>3</sub> to catalyze the arylation of maleimides to yield 3-aryl succinimides in a straightforward manner following a Friedel–Crafts-type addition. The inclusion of a selenocyanate group contributes to the cytotoxic activity of the adduct. This derivatization (from compound <b>7</b> to compound <b>15</b>) results in an average GI<sub>50</sub> value of 1.98 µM in the DTP (NCI-60) cell panel, resulting in being especially active in renal cancer cells.https://www.mdpi.com/1420-3049/27/3/982thiopheneselenopheneDiels–AldercycloaditionFriedel–Crafts alquilationselenium |
| spellingShingle | Gorka Calvo-Martín Daniel Plano Carmen Sanmartín New Experimental Conditions for Diels–Alder and Friedel-Crafts Alquilation Reactions with Thiophene: A New Selenocyanate with Potent Activity against Cancer Molecules thiophene selenophene Diels–Alder cycloadition Friedel–Crafts alquilation selenium |
| title | New Experimental Conditions for Diels–Alder and Friedel-Crafts Alquilation Reactions with Thiophene: A New Selenocyanate with Potent Activity against Cancer |
| title_full | New Experimental Conditions for Diels–Alder and Friedel-Crafts Alquilation Reactions with Thiophene: A New Selenocyanate with Potent Activity against Cancer |
| title_fullStr | New Experimental Conditions for Diels–Alder and Friedel-Crafts Alquilation Reactions with Thiophene: A New Selenocyanate with Potent Activity against Cancer |
| title_full_unstemmed | New Experimental Conditions for Diels–Alder and Friedel-Crafts Alquilation Reactions with Thiophene: A New Selenocyanate with Potent Activity against Cancer |
| title_short | New Experimental Conditions for Diels–Alder and Friedel-Crafts Alquilation Reactions with Thiophene: A New Selenocyanate with Potent Activity against Cancer |
| title_sort | new experimental conditions for diels alder and friedel crafts alquilation reactions with thiophene a new selenocyanate with potent activity against cancer |
| topic | thiophene selenophene Diels–Alder cycloadition Friedel–Crafts alquilation selenium |
| url | https://www.mdpi.com/1420-3049/27/3/982 |
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