A series of N- and O- alkylated nicotinonitriles was reported. Base mediate alkylation of nicotinonitriles 1a-c with chloroacetonitrile, allyl bromide and propargyl bromide produced N- and O- alkylated nicotinonitrile derivatives 3-6. Reaction of compounds 6a,b with ethyl 2- azidoacetate in the presence of CuSO4 and sodium ascorbate afforded 1,4-disubstituted triazoles 7a,b. The anticancer activity against RPE-1 and MCF-7 human cell lines showed that all compounds did not showed big variation in their cytotoxicity activities at concentrations of 25, 50 and 100 μM against both cell types. The antimicrobial activity of the new compounds showed that all the tested compounds do not showed significant antibacterial and antifungal activities against the mention microorganisms, except compounds 4b, 5c, 5d and 6b showed moderate antimicrobial activity towards Bacillus subtilis.