Literature DB >> 30034593

Novel Nonsteroidal Progesterone Receptor (PR) Antagonists with a Phenanthridinone Skeleton.

Yuko Nishiyama1, Shuichi Mori2, Makoto Makishima3, Shinya Fujii1, Hiroyuki Kagechika2, Yuichi Hashimoto1, Minoru Ishikawa1.   

Abstract

The progesterone receptor (PR) plays an important role in various physiological systems, including female reproduction and the central nervous system, and PR antagonists are thought to be effective not only as contraceptive agents and abortifacients but also in the treatment of various diseases, including hormone-dependent cancers and endometriosis. Here, we identified phenanthridin-6(5H)-one derivatives as a new class of PR antagonists and investigated their structure-activity relationships. Among the synthesized compounds, 37, 40, and 46 exhibited very potent PR antagonistic activity with high selectivity for PR over other nuclear receptors. These compounds are structurally distinct from other nonsteroidal PR antagonists, including cyanoaryl derivatives, and should be useful for further studies of the clinical utility of PR antagonists.

Entities:  

Year:  2018        PMID： 30034593      PMCID： PMC6047039          DOI： 10.1021/acsmedchemlett.8b00058

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  19 in total

1.  Progestin regulation of alkaline phosphatase in the human breast cancer cell line T47D.

Authors:  D Di Lorenzo; A Albertini; D Zava
Journal:  Cancer Res       Date:  1991-08-15       Impact factor: 12.701

2.  6-arylcoumarins as novel nonsteroidal type progesterone antagonists: an example with receptor-binding-dependent fluorescence.

Authors:  Haruka Sakai; Tomoya Hirano; Shuichi Mori; Shinya Fujii; Hiroyuki Masuno; Marie Kinoshita; Hiroyuki Kagechika; Aya Tanatani
Journal:  J Med Chem       Date:  2011-10-05       Impact factor: 7.446

3.  Novel 3-aryl indoles as progesterone receptor antagonists for uterine fibroids.

Authors:  Timothy I Richardson; Christian A Clarke; Kuo-Long Yu; Ying K Yee; Thomas J Bleisch; Jose E Lopez; Scott A Jones; Norman E Hughes; Brian S Muehl; Charles W Lugar; Terry L Moore; Pamela K Shetler; Richard W Zink; John J Osborne; Chahrzad Montrose-Rafizadeh; Nita Patel; Andrew G Geiser; Rachelle J Sells Galvin; Jeffrey A Dodge
Journal:  ACS Med Chem Lett       Date:  2010-12-09       Impact factor: 4.345

4.  Development of N-(4-Phenoxyphenyl)benzenesulfonamide Derivatives as Novel Nonsteroidal Progesterone Receptor Antagonists.

Authors:  Ayumi Yamada; Yuko Kazui; Hiromasa Yoshioka; Aya Tanatani; Shuichi Mori; Hiroyuki Kagechika; Shinya Fujii
Journal:  ACS Med Chem Lett       Date:  2016-09-15       Impact factor: 4.345

5.  Progesterone receptor isoforms A and B: temporal and spatial differences in expression during murine mammary gland development.

Authors:  Mark D Aupperlee; Kyle T Smith; Anastasia Kariagina; Sandra Z Haslam
Journal:  Endocrinology       Date:  2005-05-05       Impact factor: 4.736

Review 6.  Progesterone, brain-derived neurotrophic factor and neuroprotection.

Authors:  M Singh; C Su
Journal:  Neuroscience       Date:  2012-10-02       Impact factor: 3.590

7.  6-Aryl-1,4-dihydro-benzo[d][1,3]oxazin- 2-ones: a novel class of potent, selective, and orally active nonsteroidal progesterone receptor antagonists.

Authors:  Puwen Zhang; Eugene A Terefenko; Andrew Fensome; Jay Wrobel; Richard Winneker; Scott Lundeen; Keith B Marschke; Zhiming Zhang
Journal:  J Med Chem       Date:  2002-09-26       Impact factor: 7.446

8.  Development of Tetrachlorophthalimides as Liver X Receptor β (LXRβ)-Selective Agonists.

Authors:  Sayaka Nomura; Kaori Endo-Umeda; Makoto Makishima; Yuichi Hashimoto; Minoru Ishikawa
Journal:  ChemMedChem       Date:  2016-09-30       Impact factor: 3.466

9.  Synthesis and structure-activity relationship of novel 6-aryl-1,4-dihydrobenzo[d][1,3]oxazine-2-thiones as progesterone receptor modulators leading to the potent and selective nonsteroidal progesterone receptor agonist tanaproget.

Authors:  Andrew Fensome; Reinhold Bender; Rajiv Chopra; Jeff Cohen; Mark A Collins; Valerie Hudak; Karl Malakian; Susan Lockhead; Andrea Olland; Kristine Svenson; Eugene A Terefenko; Ray J Unwalla; James M Wilhelm; Scott Wolfrom; Yuan Zhu; Zhiming Zhang; Puwen Zhang; Richard C Winneker; Jay Wrobel
Journal:  J Med Chem       Date:  2005-08-11       Impact factor: 7.446

10.  Preliminary report on the treatment of endometriosis with low-dose mifepristone (RU 486).

Authors:  L M Kettel; A A Murphy; A J Morales; S S Yen
Journal:  Am J Obstet Gynecol       Date:  1998-06       Impact factor: 8.661
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  3 in total

1.  Catalytic Enantioselective Birch-Heck Sequence for the Synthesis of Phenanthridinone Derivatives with an All-Carbon Quaternary Stereocenter.

Authors:  Mary Sexton; William P Malachowski; Glenn P A Yap; Diana Rachii; Greg Feldman; Andrew T Krasley; Zhilin Chen; My Anh Tran; Kalyn Wiley; Alexandra Matei; Samantha Petersen; Sabrina Tran Tien
Journal:  J Org Chem       Date:  2022-01-05       Impact factor: 4.198

2.  Efficient Lead Finding, Activity Enhancement and Preliminary Selectivity Control of Nuclear Receptor Ligands Bearing a Phenanthridinone Skeleton.

Authors:  Yuko Nishiyama; Shinya Fujii; Makoto Makishima; Yuichi Hashimoto; Minoru Ishikawa
Journal:  Int J Mol Sci       Date:  2018-07-18       Impact factor: 5.923

3.  StackPR is a new computational approach for large-scale identification of progesterone receptor antagonists using the stacking strategy.

Authors:  Nalini Schaduangrat; Nuttapat Anuwongcharoen; Mohammad Ali Moni; Pietro Lio'; Phasit Charoenkwan; Watshara Shoombuatong
Journal:  Sci Rep       Date:  2022-09-30       Impact factor: 4.996
  3 in total

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