A series of novel 3-(substituted phenyl)-2-[5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl]acrylonitriles were designed computationally based on the therapeutic benefits of 1,3,4-oxadiazole, nicotinoyl and arylacrylonitrile derivatives. The drug-likeness of title compounds were predicted by calculating molecular properties using Molinspiration Cheminformatics and OSIRIS Property Explorer. In addition, the bioactivity score and toxicity of all the compounds were estimated. The results of in silico screening indicated that all the compounds obeyed the Lipinski’s rule of five indicating good oral bioavailability. All the evaluated title compounds were identified as kinase inhibitors. The drug-likeness and drug score of the title compounds were good. Among all, compound with trimethoxy substitution on phenyl ring showed highest drug score.