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Steroid based cancer chemotherapeutic agents of the type 2′-amino-3′-cyanocholest-6-eno[5,7-de]4H-pyrans (1c–3c) have been synthesized and characterized by the various spectroscopic and analytical techniques. The DNA binding studies of compounds (1c–3c) with CT DNA were carried out by UV–vis and fluorescence spectroscopy and gel electrophoresis. The compounds (1c–3c) bind to DNA preferentially through electrostatic and hydrophobic interactions with K_b values found to be 5.4 × 10³, 2.3 × 10³ M⁻¹ and 1.97 × 10³ M⁻¹, respectively indicating the higher binding affinity of compound (1c) towards DNA. The molecular docking study suggested that the electrostatic interaction of compounds (1c–3c) in between the nucleotide base pairs is due to the presence of pyran moiety in steroid molecule. All the compounds (1c–3c) cleave supercoiled pBR322 DNA via hydrolytic pathway, as validated by T4 …