Synthesis and transformations of polyhedral compounds. XIII. Search for antitumor agents among the indolyl-1,3-diazaadamantanes

In earlier published work, we described the role of the carboxyl group on the sulfonamide-substituted indole molecule in the manifestation of anti-blastemic activity [7]. With the aim of producing effective antitumor materials, we carried out the replacement of the carboxyl group in these compounds with the 1,3-diazaadamantane residue, other derivatives of which also show experimental antitumor activity [I]. The compounds were obtained by condensation of 3-formyl-5-dimethylaminosulfonylindoles (I) with 1,5-dimethyl-9-oxo-3,7-diazabicyclo[3,3,1]-nonane (II) analogously with our earlier synthesis of 2-(indolyl-3)-5,7dimethyl-6-oxo-l,3-diazaadamantane (IIIa) [5]. We also synthesized a series of compounds with substituents in positions i, 2, and 5 of the indole ring (IIIb-l) to show the role of the indole ring substituents on the manifestation of antitumor activity (Table i).