A series of benzoxazole and derivatives of heterocyclic bearing nitrogen, oxygen and oxazole moieties constitutes the core structure of a several biological active compounds. Based on these findings, a series of benzoic acid substituted benzoxazole were synthesized by refluxing CS2 and o-aminophenol. Compounds were characterized by IR, 1H NMR, and 13C NMR. All the compounds were tested for their anticancer activity against MCF-7 breast cancer cell line with MTT assay. Most of the compounds showed moderate to good anti-breast cancer activity. Docking studies of the synthesized compounds was done with the help of iGEMDOCKv2.1 software using GRIP batch docking method to study their observed activity