{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,15]],"date-time":"2026-06-15T17:15:07Z","timestamp":1781543707835,"version":"3.54.5"},"reference-count":23,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2022,3,11]],"date-time":"2022-03-11T00:00:00Z","timestamp":1646956800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"University of Bia\u0142ystok","award":["BST-124"],"award-info":[{"award-number":["BST-124"]}]},{"DOI":"10.13039\/501100010607","name":"University of Perugia","doi-asserted-by":"publisher","award":["Fondo per la Ricerca di Base 2019"],"award-info":[{"award-number":["Fondo per la Ricerca di Base 2019"]}],"id":[{"id":"10.13039\/501100010607","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Here we report the reaction in the biphasic system of the in situ prepared selenols and thiols with 1,4-androstadiene-3,17-dione (1) or prednisone acetate (2) having \u03b1,\u03b2-unsaturated ketone as an electrophilic functionalization. The Michael-type addition reaction resulted to be chemo- and stereoselective, affording a series of novel steroidal selenides and sulfides. This is an example of a one-step, eco-friendly process that bypasses some of the main concerns connected with the bad smell and the toxicity of these seleno- and thio-reagents. Furthermore, we demonstrated that the proposed methodology offers the possibility to prepare libraries of steroids variously and selectively decorated with different organochalcogen moieties at the C1 position starting from 1,4-androstadienic skeletons and leaving unaltered the C4\u2013C5 unsaturation. Based on the data reported in the literature the introduction of an organoselenium or an organosulfur moiety in a steroid could provide new interesting pharmaceutically active entities exerting anticancer and antimicrobial activities. In this optic, new synthetic strategies to efficiently prepare this class of compounds could be strongly desirable.<\/jats:p>","DOI":"10.3390\/ijms23063022","type":"journal-article","created":{"date-parts":[[2022,3,11]],"date-time":"2022-03-11T12:58:36Z","timestamp":1647003516000},"page":"3022","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Simple Zn-Mediated Seleno- and Thio-Functionalization of Steroids at C-1 Position"],"prefix":"10.3390","volume":"23","author":[{"given":"Pawe\u0142 A.","family":"Grze\u015b","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, University of Bia\u0142ystok, ul. Cio\u0142kowskiego 1K, 15-245 Bia\u0142ystok, Poland"},{"name":"Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06132 Perugia, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8490-7720","authenticated-orcid":false,"given":"Bonifacio","family":"Monti","sequence":"additional","affiliation":[{"name":"Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06132 Perugia, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1087-8154","authenticated-orcid":false,"given":"Natalia","family":"Wawrusiewicz-Kurylonek","sequence":"additional","affiliation":[{"name":"Department of Clinical Genetics, Diabetology and Internal Medicine, Medical University of Bia\u0142ystok, Sk\u0142odowska\u2013Curie 24A, 15-276 Bia\u0142ystok, Poland"},{"name":"Department of Endocrinology, Diabetology and Internal Medicine, Medical University of Bia\u0142ystok, Sk\u0142odowska\u2013Curie 24A, 15-276 Bia\u0142ystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0622-4561","authenticated-orcid":false,"given":"Luana","family":"Bagnoli","sequence":"additional","affiliation":[{"name":"Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06132 Perugia, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6199-7399","authenticated-orcid":false,"given":"Luca","family":"Sancineto","sequence":"additional","affiliation":[{"name":"Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06132 Perugia, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3268-3515","authenticated-orcid":false,"given":"Izabella","family":"Jastrzebska","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Bia\u0142ystok, ul. Cio\u0142kowskiego 1K, 15-245 Bia\u0142ystok, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7698-8970","authenticated-orcid":false,"given":"Claudio","family":"Santi","sequence":"additional","affiliation":[{"name":"Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06132 Perugia, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,3,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"97","DOI":"10.2174\/2212796810666160120220725","article-title":"An Update on \u201cSelenium Containing Compounds from Poison to Drug Candidates: A Review on the GPx-like Activity\u201d","volume":"9","author":"Mangiavacchi","year":"2016","journal-title":"Curr. Chem. 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