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Design and synthesis of novel androgen receptor antagonists with sterically bulky icosahedral carboranes.

Abstract：

:Carboranes (dicarba-closo-dodecaboranes) are a class of carbon-containing polyhedral boron-cluster compounds having remarkable chemical and thermal stability, and hydrophobic character. These features may allow application of carboranes as a new hydrophobic core structure in biologically active molecules that interact hydrophobically with receptors. Here, we report the design and synthesis of novel androgen antagonists bearing a carborane moiety. These compounds, particularly 8a, 8c, and 9d, exhibited anti-androgenic activity similar to that of the well-known anti-androgen flutamide in reporter gene assay using NIH3T3 cells transfected with a human AR expression plasmid. The carborane cage seems to be a privileged hydrophobic pharmacophore for the expression of AR-antagonistic activity.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Goto T,Ohta K,Suzuki T,Ohta S,Endo Y

doi

10.1016/j.bmc.2005.06.061

subject

Has Abstract

pub_date

2005-12-01 00:00:00

pages

6414-24

issue

23

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(05)00601-2

journal_volume

13

pub_type

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