Abstract
We designed and synthesized novel pyrrole-2-carboxamide derivatives as androgen antagonists. Compounds 10 and 13 bearing benzylamine or aniline at the 4-position of the pyrrole ring showed moderate androgen antagonistic activity, and inhibited the androgen-dependent growth of Shionogi carcinoma cells (SC-3). Study of the structure-activity relationships of compound 13 led to a potent androgen antagonist 36, which has higher affinity than flutamide (4) for androgen nuclear receptor (AR). Thus, pyrrole-2-carboxamide is a new scaffold for developing AR antagonists.
| Original language | English |
|---|---|
| Pages (from-to) | 2837-2846 |
| Number of pages | 10 |
| Journal | Bioorganic and Medicinal Chemistry |
| Volume | 13 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - Apr 15 2005 |
Keywords
- Androgen
- Antagonist
- Pyrrole-2-carboxamides
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry
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Cite this
Wakabayashi, K. I., Miyachi, H., Hashimoto, Y., & Tanatani, A. (2005). Novel non-steroidal/non-anilide type androgen antagonists: Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands. Bioorganic and Medicinal Chemistry, 13(8), 2837-2846. https://doi.org/10.1016/j.bmc.2005.02.019