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Polycystic Ovary Syndrome (PCOS) is a widespread and complex hormonal disorder occurs in women of reproductive age, characterized by hormonal imbalances and ovarian dysfunction. Current approaches to treating PCOS often address specific symptoms, highlighting the demand for innovative therapeutic agents that can tackle its multifaceted nature. The present study endeavors to investigate the potential of new chromen‐2‐one derivatives in the management of PCOS. A total of 30 derivatives have been synthesized and evaluated for their in vitro inhibitory effects on 5‐α reductase and antioxidant activities. Based on the promising in vitro activity and acute toxicity profile of 4‐methoxy‐N‐(3‐(4‐methoxyphenyl)‐2‐oxo‐2H‐chromen‐6‐yl) benzamide (29), it was selected for subsequent in vivo investigation in experimental animal models of PCOS. The study also includes molecular interaction analysis through docking and dynamic studies of compound (29). [ABSTRACT FROM AUTHOR]