Matrilysin　is　an　ideal　biological　target　to　develop　novel　inhibitors　because　it　is　overexpressed　in　malignant　tumour　cells.　A　series　of　3,9-diazatetraasteranes　was　designed　as　inhibitors　of　matrilysin,　which　was　an　ideal　biological　target　because　it　is　responsible　for　aggressive　malignant　phenotypes　and　poor　prognoses　implicated　in　many　cancers.　Docking　simulation　supported　the　initial　pharmacophore　hypothesis　and　suggested　a　common　interaction　mechanism　of　3,9-diazatetraasteranes　with　the　catalytic　site　of　matrilysin.　The　3,9-diazatetraasteranes　were　synthesized　by　the　photocyclization　of　4-aryl-1,4-dihydropyridines,　and　their　structures　were　determined　using　H-1　NMR,　C-13　NMR　and　MS.　The　inhibitory　activities　of　these　compounds　on　matrilysin　were　investigated　in　vitro　using　an　MTT　assay　in　A549　(small　cell　lung　cancer)　cells.　The　results　show　that　the　3,9-diazatetraasteranes　can　inhibit　the　growth　of　A549　tumour　cells.　The　best　IC50　value　is　approximately　50m.　This　result　indicates　that　3,9-diazatetraasteranes　will　be　useful　pharmacological　tools　for　the　investigation　of　matrilysin　inhibitors.