Synthesis and Antibacterial and Antitumor Activity of 2-Sulfanyl-Substituted 3H-Spiro[Benzo[H]Quinazoline-5,1'-Cycloheptane]-4(6H)-Ones

The reaction of ethyl 4'-amino-1'H-spiro[cycloheptane-1,2'-naphthalene]-3'-carboxylate with benzoyl isothiocyanate produced ethyl 4'-(3-benzoylthioureido)-1'H-spiro[cycloheptane-1,2'-naphthalene]-3'-carboxylate, cyclization of which led to the formation of 2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1'-cycloheptane]-4(6H)-one. Condensation of the last with halides of various structures in the presence of KOH led to the formation of 2-sulfanyl-substituted 3H-spiro[benzo[h]quinazoline-5,1'-cycloheptane]-4(6H)-ones. The antibacterial properties and antitumor activity against sarcoma 180 of the obtained compounds were studied. Gram-positive (Staphylococcus aureus 209p, Bacillus subtilis ATCC 6633) and Gram-negative microorganisms (Sh. flexneri 6858, E. coli 0-55) were used as test objects. The activities of the studied compounds were markedly inferior to that of the reference drug furazolidone. All studied compounds exhibited weak antitumor activity. They inhibited growth of sarcoma 180 by 24 - 33% (p < 0.05) in mice at doses of 155 - 170 mg/kg.