2-Hydroxymethyl-1-naphthol diacetate (TAC) and sixteen Mannich base derivatives of naphthol were prepared and examined for cytotoxicity and antimicrobial activity. Cytotoxicity was examined against four human carcinoma cell lines. Several derivatives were effective at concentrations < 4 micrograms/ml. TAC showed the highest cytotoxicity. Inhibition of DNA-, RNA-, and protein synthesis by TAC was also studied and discussed. TAC also exhibits potent antimicrobial activity against Enterobacter clocae 23355, Klebsiella pneumonia 13883, Proteus vulgaris 13315, Pseudomonas aeruginosa 27853, Candida parapsilosis, Candida tropicalis, Trichosposon beigelli, and Rhodotorul spp. with minimum inhibitory concentrations of 0.1-0.4 microM. These results indicate that esterification by Bruson reaction of 1-naphthol Mannich base to TAC enhances the cytotoxicity and antimicrobial activity.