Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4-Oxadiazin-5(6H)-one Derivatives from Dehydroabietic Acid

A series of new 1,3,4-oxadiazin-5(6H)-one derivatives (6a-n) of dehydroabietic acid were designed and synthesized as potential antimicrobial and antitumor agents. Their structures were characterized by IR, H-1 NMR, C-13 NMR, MS, and elemental analyses. All the title compounds were evaluated for their antimicrobial activity against four bacterial and three fungal strains using the serial dilution method. Among them, compound 6e showed the highest antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) value of 1.9 g/mL. In addition, the in vitro cytotoxic activities of the title compounds were also assayed against three human carcinoma cell lines (MCF-7, SMMC-7721, and HeLa) through the MTT colorimetric method. As a result, compounds 6b, 6g, 6k, and 6m exhibited significant inhibition against at least one cell line with IC50 values below 10 M. Compound 6m was especially found to be the most potent derivative with IC50 values of 2.26 +/- 0.23, 0.97 +/- 0.11, and 1.89 +/- 0.31M against MCF-7, SMMC-7721, and HeLa cells, respectively, comparable to positive control etoposide.