Synthesis of novel boronated acridines- and spermidines as possible agents for BNCT

An approach to synthesise three different boronated DNA-interacting compounds (11, 15 gr 19) is described. Compound 11 is containing both an acridine system and a spermidine residue. The acridine moiety would serve as DNA-intercalating fragment whereas the spermidine residue functions both as water-solubilising and DNA-interacting part 1,12-p-Carboranyl bis[(N-3-aminopropyl, N-4-aminobutyl)-3-propane amide] hydrogen chloride (15) was obtained by treating 13 first with ethyl chloroformate and then the secondary amine 2 Finally, 1, 12-Bis(N-(9-acridinyl)3-aminopropyl)-p-carborane hydrogen chloride (19) was accomplished by hydrochloronation of the corresponding free amine which was obtained by the treatment of 18 with 9 in toluene/DMF. (C) 1998 Elsevier Science Ltd. All rights reserved.