{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,18]],"date-time":"2026-03-18T08:04:01Z","timestamp":1773821041481,"version":"3.50.1"},"reference-count":58,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2024,4,2]],"date-time":"2024-04-02T00:00:00Z","timestamp":1712016000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"JSPS","award":["23K06046"],"award-info":[{"award-number":["23K06046"]}]},{"name":"JSPS","award":["JP23ama121043"],"award-info":[{"award-number":["JP23ama121043"]}]},{"name":"Takeda Science Foundation","award":["23K06046"],"award-info":[{"award-number":["23K06046"]}]},{"name":"Takeda Science Foundation","award":["JP23ama121043"],"award-info":[{"award-number":["JP23ama121043"]}]},{"name":"Hoansha Fundation","award":["23K06046"],"award-info":[{"award-number":["23K06046"]}]},{"name":"Hoansha Fundation","award":["JP23ama121043"],"award-info":[{"award-number":["JP23ama121043"]}]},{"name":"Research Center for Biomedical Engineering","award":["23K06046"],"award-info":[{"award-number":["23K06046"]}]},{"name":"Research Center for Biomedical Engineering","award":["JP23ama121043"],"award-info":[{"award-number":["JP23ama121043"]}]},{"DOI":"10.13039\/100009619","name":"AMED","doi-asserted-by":"publisher","award":["23K06046"],"award-info":[{"award-number":["23K06046"]}],"id":[{"id":"10.13039\/100009619","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009619","name":"AMED","doi-asserted-by":"publisher","award":["JP23ama121043"],"award-info":[{"award-number":["JP23ama121043"]}],"id":[{"id":"10.13039\/100009619","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>We previously revealed that phosphine\u2013boranes can function as molecular frameworks for biofunctional molecules. In the present study, we exploited the diversity of available phosphines to design and synthesize a series of B-(trifluoromethyl)phenyl phosphine\u2013borane derivatives as novel progesterone receptor (PR) antagonists. We revealed that the synthesized phosphine\u2013borane derivatives exhibited LogP values in a predictable manner and that the P\u2013H group in the phosphine\u2013borane was almost nonpolar. Among the synthesized phosphine\u2013boranes, which exhibited PR antagonistic activity, B-(4-trifluoromethyl)phenyl tricyclopropylphosphine\u2013borane was the most potent with an IC50 value of 0.54 \u03bcM. A docking simulation indicated that the tricyclopropylphosphine moiety plays an important role in ligand\u2013receptor interactions. These results support the idea that phosphine\u2013boranes are versatile structural options in drug discovery, and the developed compounds are promising lead compounds for further structural development of next-generation PR antagonists.<\/jats:p>","DOI":"10.3390\/molecules29071587","type":"journal-article","created":{"date-parts":[[2024,4,2]],"date-time":"2024-04-02T09:36:54Z","timestamp":1712050614000},"page":"1587","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Design, Synthesis, and Evaluation of B-(Trifluoromethyl)phenyl Phosphine\u2013Borane Derivatives as Novel Progesterone Receptor Antagonists"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-6802-4655","authenticated-orcid":false,"given":"Yu","family":"Miyajima","sequence":"first","affiliation":[{"name":"Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kotaro","family":"Ochiai","sequence":"additional","affiliation":[{"name":"Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shinya","family":"Fujii","sequence":"additional","affiliation":[{"name":"Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,4,2]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4023","DOI":"10.1021\/cr100105a","article-title":"Amine\u2212 and phosphine\u2212 borane adducts: New interest in old molecules","volume":"110","author":"Staubitz","year":"2010","journal-title":"Chem. 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