In the present investigation, azo compounds were synthesized in good yields via the diazotization of different aromatic amines followed by coupling with indole. The synthesized compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR and mass spectral techniques and have been tested in vitro against a number of microorganisms in order to assess their antimicrobial properties using disk diffusion method and the minimum inhibitory concentrations (MIC) by the broth micro dilution technique. Their anticancer activity against human breast cancer cell line (MCF7) was determined by MTT assay. All exhibit comparable biological activity.