Substituted N-aminothioglycolurils containing thiosemicarbazone moiety and their cytotoxic activity in vitro.
A library of hybrid molecules bearing thioglycoluril and (hetero)aromatic aldehyde thiosemicarbazone moieties was synthesized via a tandem hydrazone formation-ring contraction reaction of 5,7-dialkyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-ones with (hetero)aromatic aldehydes. All synthesized compounds were tested for their cytotoxic activity against rhabdomyosarcoma, A549, and MS human cancer cell lines by MTT-assay. Among the derivatives, (E)-4-benzylideneamino-1,3-dimethyl-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-one 1f was found to have the most marked antiproliferative activity toward the tested cell lines (1f: IC[Formula: see text] 23.7, and 6.4 [Formula: see text]M, respectively). The IC[Formula: see text] value of thioglycoluril 1f against normal human embryonic kidney cells HEK293 was 72.5 [Formula: see text]M, which appeared to be 3-11-fold higher than IC[Formula: see text] values of 1f against human cancer cells.
['Gazieva|Galina A|GA|', 'Anikina|Lada V|LV|', 'Pukhov|Sergei A|SA|', 'Karpova|Tatyana B|TB|', 'Nelyubina|Yulia V|YV|', 'Kravchenko|Angelina N|AN|']
D000970:Antineoplastic Agents D017209:Apoptosis D045744:Cell Line, Tumor D002470:Cell Survival D006801:Humans D020128:Inhibitory Concentration 50 D015394:Molecular Structure D013329:Structure-Activity Relationship D013882:Thiosemicarbazones
Cytotoxic activity Thioglycolurils 5-Thioxohexahydroimidazo[45-d]imidazol-2(1H)-one Cyclic thiosemicarbazones