Synthesis of novel naphtho[2,1-b]-1,4,5-oxa- or thiadiazepines as potential antimicrobial and anticancer agents

Two novel series of quinone derivatives have been synthesized. Thus, condensation of 2-ethoxycarbonylmethylthio-; 3-ethoxycarbonylmethylthio-2-methyl- and 3-ethoxycarbonylmethoxy-2-methyl derivatives of 1,4-naphthoquinone with substituted phenylhydrazines afforded the corresponding hydrazones, while cyclization of the same quinones with the same substituted hydrazines in glacial acetic acid gave the corresponding naphtho[2,1-b]-1,4,5-oxa- or thiadiazepine derivatives. The antimicrobial and anticancer activities of the synthesized compounds were studied.