The most challenge task in the building up of surface-active molecules is maximizing their surface activity with good biological activity. A nonionic surfactant (N-isatin-EO m -C n where m is 5, 7 and 9 ethylene glycol units and n is 8, 10 and 12) is achieved by first reacting isatin with chloroacetic acid and then with different types of ethoxylated (C 8 -C 12 ) fatty alcohols that possess 5, 7 and 9 ethylene oxide units. The prepared surfactants were characterized by FTIR and 1 H NMR to confirm the structure. The surface activity, biodegradability, antimicrobial, and antifungal activity of the surfactants were evaluated. In addition, quantum chemical calculations and computations of oral bioavailability were performed. The obtained data show that all the synthesized compounds had good surface activity, biodegradability and biological activity.