Synthesis and Biological Activity of 3-Substituted 1H-Spiro[Benzo[ h ]-Quinazoline-5,1 ' -Cycloheptane]-2,4(3 H ,6 H )-Diones

A method for the synthesis of ethyl 4'-(phenoxycarbonylamino)-1'H-spiro[cycloheptane-1,2'-naphthalene]-3'-carboxylate from ethyl 4'-amino-1'H-spiro[cycloheptane-1,2'-naphthalene]-3'-carboxylate (aminoester) was developed. Reaction of the former with primary amines produced 3-substituted 1H-spiro[benzo-[h ]quinazoline-5,1'-cycloheptane]-2,4(3H,6H)-diones. Condensation of the aminoester with m-chlorophenylisocyanate synthesized ethyl 4'-{[(3-chlorophenyl)carbamoyl]imino}-3',4'-dihydro-1'H-spiro(cycloheptane-1,2'-naphthalene)-3'-carboxylate, which cyclized into 3-(3-chlorophenyl)-1H-spiro[benzo[h ]quinazoline-5,1'-cycloheptane]-2,4(3H,6H)-dione. The synthesized compounds were shown to possess antitumor and anti-monoamine oxidase activities.