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Paper | Special issue | Vol 99, No. 1, 2019, pp.425-445
Published online, 15th October, 2018
DOI: 10.3987/COM-18-S(F)38
Design and Synthesis of Cyclohexenyl-p-carborane Derivatives as a New Class of Progesterone Receptor Antagonists

Shinya Fujii, Naoki Yanagida, Shuichi Mori, Emiko Kawachi, and Hiroyuki Kagechika*

* Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan


We report here the synthesis and structure-activity relationships of a series of C-cyclohexenyl-p-carborane derivatives, which we designed as candidates for a novel class of progesterone receptor (PR) antagonists. Biological evaluation using T47D alkaline phosphatase assay revealed that several compounds exhibited potent PR-antagonistic activity. We also examined the selectivity of these compounds for PR over androgen receptor (AR). Among them, 11b functioned as a PR-selective antagonist, while other compounds, such as 13b, acted as PR/AR dual antagonists. Notably, docking simulations indicated that 11b and 13b bind in similar orientations to the ligand-binding site of PR, but in opposite orientations to that of AR. These findings could helpful for developing more selective ligands for PR.