Some Transformations of 2-Thioxo-2,3-Dihydro-1H-Spiro-[Benzo[h]Quinazoline-5,1′-Cycloheptan]-4(6H)-One and the Antibacterial and Antitumor Properties of the Compounds Synthesized

Condensation reactions of 2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one with 2-aminoethanol and 3-aminopropanol were used to synthesize 2-[(2-hydroxyethyl)amino]-3Hspiro[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one and 2-[(3-hydroxypropyl)amino]-3H-spiro[benzo-[h]quinazoline-5,1′-cycloheptan]-4(6H)-one respectively. Interaction of this thioxoquinazoline with 2-chloromethylbenzoquinazolines with different structures yielded dibenzoquinazoline systems connected at position 2 by an -SCH₂- linker. Reactions using methylene iodide produced 2,2’-[methylenebis(sulfanediyl)]-bis(3H-spiro[benzo[h]quinazoline-5,1′-cycloheptan]-4(6H)-one, while use of 1,2-dibromoethane, 2,3-dibromoacetic acid ethyl ester, and 1,3-dibromopropane led to the production of 9,10-dihydrospiro[benzo-[h]thiazolo[2, 3-b]quinazoline-6,1′-cycloheptan]-7(5H)-one, ethyl-7-oxo-5,7,9,10-tetrahydrospiro[benzo[h]-thiazolo[2,3-b]quinazoline-6,1′-cycloheptan]-9-carboxylate, and 10,11-dihydro-5H-spiro[benzo[h][1,3]-thiazino[2,3-b]quinazoline-6,1′-cycloheptan]-7(9H)-one respectively. The study compounds were found to have activity which was significantly inferior to that of reference antimicrobial drug furazolidone. Study compounds at doses of 150–185 mg/kg exhibited antitumor activity, inhibiting tumor growth in mice by 20–40%.