We report the synthesis and a study of the structure activity relationships of a new series of diarylhydrazides as potential selective non-Ligand Binding Pocket Androgen Receptor antagonists. Their biological activity as antiandrogens in the context of the development of treatments for castration resistant prostate cancer was evaluated using in vitro using Time Resolved Fluorescence Resonance Energy Transfer and Fluorescence Polarisation on target assays. Additionally, a theoretical study combining docking and molecular dynamics methods was performed to provide insight to their mechanism of action as a basis for further lead optimisation studies.