Synthesis and evaluation of bile acid amides of [Formula: see text]-cyanostilbenes as anticancer agents

Abstract

A series of amino-substituted α-cyanostilbene derivatives and their bile acid (cholic and deoxycholic acid) amides were designed and synthesized. A comparative study on the anticancer and antibacterial activity evaluation on the synthesized analogs was carried against the human osteosarcoma (HOS) cancer cell line, and two gram −ve (E. coli and S. typhi) and two gram +ve (B. subtilis and S. aureus) bacterial strains. All the cholic acid α-cyanostilbene amides showed an IC50 in the range 2–13 μM against human osteosarcoma cells (HOS) with the most active analog (6g) possessing an IC50 of 2μM. One of the amino-substituted α-cyanostilbene, 4e, was found to possess an IC50 of 3μM. An increase in the number of cells at the sub-G1 phase of the cell was observed in the in vitro cell cycle analysis of two most active compounds in the series (4e, 6g) suggesting a clear indication toward induction of apoptotic cascade. With respect to antibacterial screening, amino-substituted α-cyanostilbenes were found to be more active than their corresponding bile acid amides. The synthesized compounds were also subjected to in silico study to predict their physiochemical properties and drug-likeness score.