{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T15:33:19Z","timestamp":1791387199012,"version":"4.3.3"},"reference-count":29,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2022,2,1]],"date-time":"2022-02-01T00:00:00Z","timestamp":1643673600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100010434","name":"Fundaci\u00f3n Bancaria Caixa d\u2019Estalvis i Pensions de Barcelona","doi-asserted-by":"publisher","award":["-"],"award-info":[{"award-number":["-"]}],"id":[{"id":"10.13039\/100010434","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005367","name":"National University of Distance Education","doi-asserted-by":"publisher","award":["--"],"award-info":[{"award-number":["--"]}],"id":[{"id":"10.13039\/501100005367","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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\u2013Alder adducts of thiophene at room temperature and atmospheric pressure. Maleimido\u2013thiophene adducts were promoted by AlCl3. 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 AlCl3 is highly stereoselective, preferably providing the exo form of the adduct. Additionally, we also discovered the ability of AlCl3 to catalyze the arylation of maleimides to yield 3-aryl succinimides in a straightforward manner following a Friedel\u2013Crafts-type addition. The inclusion of a selenocyanate group contributes to the cytotoxic activity of the adduct. This derivatization (from compound 7 to compound 15) results in an average GI50 value of 1.98 \u00b5M in the DTP (NCI-60) cell panel, resulting in being especially active in renal cancer cells.<\/jats:p>","DOI":"10.3390\/molecules27030982","type":"journal-article","created":{"date-parts":[[2022,2,1]],"date-time":"2022-02-01T22:16:18Z","timestamp":1643753778000},"page":"982","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["New Experimental Conditions for Diels\u2013Alder and Friedel-Crafts Alquilation Reactions with Thiophene: A New Selenocyanate with Potent Activity against Cancer"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2806-5183","authenticated-orcid":false,"given":"Gorka","family":"Calvo-Mart\u00edn","sequence":"first","affiliation":[{"name":"Departamento de Tecnolog\u00eda y Qu\u00edmica Farmac\u00e9uticas, Facultad de Farmacia y Nutrici\u00f3n, Universidad de Navarra, Irunlarrea 1, E-31008 Pamplona, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8266-0445","authenticated-orcid":false,"given":"Daniel","family":"Plano","sequence":"additional","affiliation":[{"name":"Departamento de Tecnolog\u00eda y Qu\u00edmica Farmac\u00e9uticas, Facultad de Farmacia y Nutrici\u00f3n, Universidad de Navarra, Irunlarrea 1, E-31008 Pamplona, Spain"},{"name":"Unidad de Onco-Hematolog\u00eda, Instituto de Investigaci\u00f3n Sanitaria de Navarra (IdiSNA), Irunlarrea 3, E-31008 Pamplona, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3431-7826","authenticated-orcid":false,"given":"Carmen","family":"Sanmart\u00edn","sequence":"additional","affiliation":[{"name":"Departamento de Tecnolog\u00eda y Qu\u00edmica Farmac\u00e9uticas, Facultad de Farmacia y Nutrici\u00f3n, Universidad de Navarra, Irunlarrea 1, E-31008 Pamplona, Spain"},{"name":"Unidad de Onco-Hematolog\u00eda, Instituto de Investigaci\u00f3n Sanitaria de Navarra (IdiSNA), Irunlarrea 3, E-31008 Pamplona, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,2,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1668","DOI":"10.1002\/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-Z","article-title":"The Diels\u2013Alder reaction in total synthesis","volume":"41","author":"Nicolaou","year":"2002","journal-title":"Angew. 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