A series of amino-substituted α\documentclass[12pt]{minimal}
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\begin{document}$$\alpha $$\end{document}-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 +\documentclass[12pt]{minimal}
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\begin{document}$$+$$\end{document}ve (B. subtilis and S. aureus) bacterial strains. All the cholic acid α\documentclass[12pt]{minimal}
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\begin{document}$$\alpha $$\end{document}-cyanostilbene amides showed an IC50\documentclass[12pt]{minimal}
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\begin{document}$$\hbox {IC}_{50}$$\end{document} in the range 2–13 μM\documentclass[12pt]{minimal}
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\begin{document}$$\upmu \hbox {M}$$\end{document} against human osteosarcoma cells (HOS) with the most active analog (6g) possessing an IC50\documentclass[12pt]{minimal}
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\begin{document}$$\hbox {IC}_{50}$$\end{document} of 2μM\documentclass[12pt]{minimal}
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\begin{document}$$2\,\upmu \hbox {M}$$\end{document}. One of the amino-substituted α\documentclass[12pt]{minimal}
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\begin{document}$$\alpha $$\end{document}-cyanostilbene, 4e, was found to possess an IC50\documentclass[12pt]{minimal}
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\begin{document}$$\hbox {IC}_{50}$$\end{document} of 3μM\documentclass[12pt]{minimal}
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\begin{document}$$3\,\upmu \hbox {M}$$\end{document}. An increase in the number of cells at the sub-G1\documentclass[12pt]{minimal}
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\begin{document}$$\hbox {G}_{1}$$\end{document} 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\documentclass[12pt]{minimal}
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\begin{document}$$\alpha $$\end{document}-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.