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Development of 1,3-diphenyladamantane derivatives as nonsteroidal progesterone receptor antagonists.
Mori, Shuichi; Takeuchi, Yuki; Tanatani, Aya; Kagechika, Hiroyuki; Fujii, Shinya.
Affiliation
  • Mori S; Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
  • Takeuchi Y; Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
  • Tanatani A; Department of Chemistry, Faculty of Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan. Electronic address: tanatani.aya@ocha.ac.jp.
  • Kagechika H; Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan.
  • Fujii S; Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan; Institute of Molecular and Cellular Biosciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan.
Bioorg Med Chem ; 23(4): 803-9, 2015 Feb 15.
Article in En | MEDLINE | ID: mdl-25593098
ABSTRACT
Nonsteroidal progesterone receptor (PR) full antagonists are needed as tools for elucidating the physiological functions of PR and as candidates for treatment of various diseases. We designed and synthesized 1,3-diphenyladamantane derivatives, and investigated their PR-antagonistic activity in comparison with our recently developed boron cluster-based PR antagonists. Among the synthesized adamantane derivatives, compound 9a exhibited the most potent PR-antagonistic activity (IC50 25nM) and showed high binding affinity for the PR ligand-binding domain, comparable with that of the boron cluster-based PR antagonists. These results suggest that disubstituted adamantane, like the boron cluster m-carborane, is a promising hydrophobic pharmacophore for further structural development of nonsteroidal PR antagonists.
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Full text: 1 Database: MEDLINE Main subject: Adamantane / Receptors, Progesterone Limits: Humans Language: En Year: 2015 Type: Article
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Full text: 1 Database: MEDLINE Main subject: Adamantane / Receptors, Progesterone Limits: Humans Language: En Year: 2015 Type: Article