Structure-property and structure-activity relationships of phenylferrocene derivatives as androgen receptor antagonists.
Androgen receptor
Antagonist
Ferrocene
Hydrophobic pharmacophore
Journal
Bioorganic & medicinal chemistry letters
ISSN: 1464-3405
Titre abrégé: Bioorg Med Chem Lett
Pays: England
ID NLM: 9107377
Informations de publication
Date de publication:
15 08 2021
15 08 2021
Historique:
received:
20
04
2021
revised:
19
05
2021
accepted:
20
05
2021
pubmed:
29
5
2021
medline:
5
1
2022
entrez:
28
5
2021
Statut:
ppublish
Résumé
Ferrocene is a representative organometallic compound having a sandwich structure with high stability and hydrophobicity. In this study, we determined the physicochemical properties of a series of nitro- and cyanophenylferrocenes, and evaluated their biological activity as androgen receptor (AR) antagonists. Ferrocene derivatives exhibited hydrophobicity parameter π values in the range between 2.54 and 3.23, depending on the substituents, indicating that the hydrophobicity of ferrocene is suitable for its application as a hydrophobic core structure of nuclear receptor ligands. The synthesized ferrocene derivatives showed AR-antagonistic activity, and among them, 3-nitrophenylferrocene 14 exhibited the most potent activity with an IC
Identifiants
pubmed: 34048883
pii: S0960-894X(21)00368-1
doi: 10.1016/j.bmcl.2021.128141
pii:
doi:
Substances chimiques
Androgen Receptor Antagonists
0
Ferrous Compounds
0
Metallocenes
0
Receptors, Androgen
0
ferrocene
U96PKG90JQ
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
128141Informations de copyright
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