The series of synthesized title compounds were characterized by spectral data and evaluated for their anticancer and anti- mycobacterial activity. By results, it is interesting to note that in general the compounds having the chlorine at 6th and 7th position on coumarin and bromine 6th position on coumarin have the exhibited potent activity compared to other substitutions. The careful observation on SAR, the compounds 10h and 10i having the chlorine at 6th and 7th position on coumarin and iodine at 4th position on phenoxy moiety exhibited potent anticancer and anti- mycobacterial activity. These two compounds are even more anti- mycobacterial than standard drugs under investigation. The higher activities of these compounds may lead to new anticancer and anti-mycobacterial drugs in future.