Abstract
•The Knoevenagel reactions of pregnenolone with -aminoprop-1-ene-1,1,3-tricarbonitrile and 3-oxo-3-phenylpropanenitrile.•Separation and structure elucidation of the E and Z stereo-isomeric products were carried out.•The cytotoxicity of the newly synthesized products was evaluated against six human cancer cell lines and one human cell line.•Some compounds showed high cytotoxicity against cancer cell lines.
The reaction of pregnenolone with either 2-aminoprop-1-ene-1,1,3-tricarbonitrile or 3-oxo-3-phenylpropanenitrile gave the Knoevenagel condensation products 3 and 6, respectively. Separation of the E and Z isomeric compounds of 3 and 6 together with their structure elucidation were carried out. Some chemical transformations of the latter products were carried out and the cytotoxicity of the newly obtained products was evaluated against some cancer cell lines and a human normal cell line. The results indicated that compounds 15, 17a, 18 and 20e among the tested compounds showed the highest cytotoxicity against the cancer cell lines.