2-Hydroxymethyl-1-naphthol diacetate (TAC) and sixteen Mannich base de
rivatives of naphthol were prepared and examined for cytotoxicity and
antimicrobial activity. Cytotoxicity was examined against four human c
arcinoma cell lines. Several derivatives were effective at concentrati
ons < 4 mu g/ml. TAC showed the highest cytotoxicity. Inhibition of DN
A-, 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, Pseu
domonas aeruginosa 27853, Candida parapsilosis, Candida tropicalis, Tr
ichosopson beigelli, and Rhodotorul spp. with minimum inhibitory conce
ntrations of 0.1 similar to 0.4 mu M. These results indicate that este
rification by Bruson reaction of 1-naphthol Mannich base to TAC enhanc
es cytotoxicity and antimicrobial activity.