Structure based approach to the design of bicyclic-1H-isoindole-1,3(2H)-dione based androgen receptor antagonists.

Article Details

Citation

Salvati ME, Balog A, Shan W, Wei DD, Pickering D, Attar RM, Geng J, Rizzo CA, Gottardis MM, Weinmann R, Krystek SR, Sack J, An Y, Kish K

Structure based approach to the design of bicyclic-1H-isoindole-1,3(2H)-dione based androgen receptor antagonists.

Bioorg Med Chem Lett. 2005 Jan 17;15(2):271-6.

PubMed ID
15603938 [ View in PubMed
]
Abstract

A novel series of isoindoledione based compounds were identified as potent antagonists of the androgen receptor (AR). Co-crystallization of members of this family of inhibitors was successfully accomplished with the T877A AR LBD. A working model of how this class of compounds functions to antagonize the AR was created. Based on this model, it was proposed that expanding the bicyclic portion of the molecule should result in analogs which function as effective antagonists against a variety of AR isoforms. In contrast to what was predicted by the model, SAR around this new series was dictated by the aniline portion rather than the bicyclic portion of the molecule.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
BicalutamideAndrogen receptorIC 50 (nM)400N/AN/ADetails
BicalutamideAndrogen receptorKi (nM)35N/AN/ADetails
BicalutamideAndrogen receptorIC 50 (nM)725N/AN/ADetails
BicalutamideAndrogen receptorIC 50 (nM)173N/AN/ADetails
BicalutamideAndrogen receptorKi (nM)64N/AN/ADetails