A novel series of benzothiazole urea and thiourea derivatives was synthesized and evaluated for its in vitro cytotoxicity against MCF-7 breast cancer cells. The N 1 -(benzothiazol-2-yl)-N 3 -morpholinourea 3 displayed the highest cytotoxic activity in this series. A docked pose of 3 was obtained bound to G-quadruplex of human telomere DNA active site using the Molecular Operating Environment (MOE) module. Moreover, the synthesized compounds were screened for their antimicrobial activity against Mycobacterium tuberculosis H 37 R v , E. coli, S. aureus and C. albicans. Again, 3 showed the best activity against M. tuberculosis H 37 R v while other compounds were equipotent with ampicillin against S. aureus and E. coli.