Six novel phane-structured diazacrowns containing g-piperidone and pyridine rings were synthesized from podand 2,6-bis(2-formylphenoxymethyl)pyridine, with the g-piperidone moiety having been constructed in the course of its domino condensation with simple ketones and ammonium acetate. The compounds were tested in vitro for antimicrobial and cytotoxic activity against four human cancer cell lines (Hep-G2, RD, MCF-7, Lu-1) and the Vero cell line. X-Ray structure study of one representative compound revealed its rac-1RS,23SR,24RS,26SR configuration.