{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T03:29:46Z","timestamp":1788492586069,"version":"build-2803163510"},"reference-count":43,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2022,11,4]],"date-time":"2022-11-04T00:00:00Z","timestamp":1667520000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Belarusian Foundation for Fundamental Research","award":["X22Mldg-001"],"award-info":[{"award-number":["X22Mldg-001"]}]},{"name":"Belarusian Foundation for Fundamental Research","award":["IGA_PrF_2022_007"],"award-info":[{"award-number":["IGA_PrF_2022_007"]}]},{"name":"Belarusian Foundation for Fundamental Research","award":["LX22NPO5102"],"award-info":[{"award-number":["LX22NPO5102"]}]},{"name":"Belarusian Foundation for Fundamental Research","award":["075-15-2022-305"],"award-info":[{"award-number":["075-15-2022-305"]}]},{"DOI":"10.13039\/501100007059","name":"Palacky University Olomouc","doi-asserted-by":"publisher","award":["X22Mldg-001"],"award-info":[{"award-number":["X22Mldg-001"]}],"id":[{"id":"10.13039\/501100007059","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007059","name":"Palacky University Olomouc","doi-asserted-by":"publisher","award":["IGA_PrF_2022_007"],"award-info":[{"award-number":["IGA_PrF_2022_007"]}],"id":[{"id":"10.13039\/501100007059","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007059","name":"Palacky University Olomouc","doi-asserted-by":"publisher","award":["LX22NPO5102"],"award-info":[{"award-number":["LX22NPO5102"]}],"id":[{"id":"10.13039\/501100007059","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007059","name":"Palacky University Olomouc","doi-asserted-by":"publisher","award":["075-15-2022-305"],"award-info":[{"award-number":["075-15-2022-305"]}],"id":[{"id":"10.13039\/501100007059","id-type":"DOI","asserted-by":"publisher"}]},{"name":"European Union","award":["X22Mldg-001"],"award-info":[{"award-number":["X22Mldg-001"]}]},{"name":"European Union","award":["IGA_PrF_2022_007"],"award-info":[{"award-number":["IGA_PrF_2022_007"]}]},{"name":"European Union","award":["LX22NPO5102"],"award-info":[{"award-number":["LX22NPO5102"]}]},{"name":"European Union","award":["075-15-2022-305"],"award-info":[{"award-number":["075-15-2022-305"]}]},{"name":"Ministry of Science and Higher Education of the Russian Federation","award":["X22Mldg-001"],"award-info":[{"award-number":["X22Mldg-001"]}]},{"name":"Ministry of Science and Higher Education of the Russian Federation","award":["IGA_PrF_2022_007"],"award-info":[{"award-number":["IGA_PrF_2022_007"]}]},{"name":"Ministry of Science and Higher Education of the Russian Federation","award":["LX22NPO5102"],"award-info":[{"award-number":["LX22NPO5102"]}]},{"name":"Ministry of Science and Higher Education of the Russian Federation","award":["075-15-2022-305"],"award-info":[{"award-number":["075-15-2022-305"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Steroids with a nitrogen-containing heterocycle in the side chain are known as effective inhibitors of androgen signaling and\/or testosterone biosynthesis, thus showing beneficial effects for the treatment of prostate cancer. In this work, a series of 3\u03b2-hydroxy-5-ene steroids, containing an isoxazole fragment in their side chain, was synthesized. The key steps included the preparation of Weinreb amide, its conversion to acetylenic ketones, and the 1,2- or 1,4-addition of hydroxylamine, depending on the solvent used. The biological activity of the obtained compounds was studied in a number of tests, including their effects on 17\u03b1-hydroxylase and 17,20-lyase activity of human CYP17A1 and the ability of selected compounds to affect the downstream androgen receptor signaling. Three derivatives diminished the transcriptional activity of androgen receptor and displayed reasonable antiproliferative activity. The candidate compound, 24j (17R)-17-((3-(2-hydroxypropan-2-yl)isoxazol-5-yl)methyl)-androst-5-en-3\u03b2-ol, suppressed the androgen receptor signaling and decreased its protein level in two prostate cancer cell lines, LNCaP and LAPC-4. Interaction of compounds with CYP17A1 and the androgen receptor was confirmed and described by molecular docking.<\/jats:p>","DOI":"10.3390\/ijms232113534","type":"journal-article","created":{"date-parts":[[2022,11,8]],"date-time":"2022-11-08T11:56:36Z","timestamp":1667908596000},"page":"13534","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis and Biological Evaluation of New Isoxazolyl Steroids as Anti-Prostate Cancer Agents"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3521-727X","authenticated-orcid":false,"given":"Anton S.","family":"Rudovich","sequence":"first","affiliation":[{"name":"Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Str., 5\/2, 220141 Minsk, Belarus"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miroslav","family":"Pe\u0159ina","sequence":"additional","affiliation":[{"name":"Department of Experimental Biology, Faculty of Science, Palack\u00fd University Olomouc, \u0160lechtitel\u016f 27, 78371 Olomouc, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anastasiya V.","family":"Krech","sequence":"additional","affiliation":[{"name":"Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Str., 5\/2, 220141 Minsk, Belarus"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria Y.","family":"Novozhilova","sequence":"additional","affiliation":[{"name":"Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Str., 5\/2, 220141 Minsk, Belarus"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anastasia M.","family":"Tumilovich","sequence":"additional","affiliation":[{"name":"Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Str., 5\/2, 220141 Minsk, Belarus"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tatyana V.","family":"Shkel","sequence":"additional","affiliation":[{"name":"Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Str., 5\/2, 220141 Minsk, Belarus"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irina P.","family":"Grabovec","sequence":"additional","affiliation":[{"name":"Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich Str., 5\/2, 220141 Minsk, Belarus"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0597-3261","authenticated-orcid":false,"given":"Miroslav","family":"Kvasnica","sequence":"additional","affiliation":[{"name":"Department of Experimental Biology, Faculty of Science, Palack\u00fd University Olomouc, \u0160lechtitel\u016f 27, 78371 Olomouc, Czech 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