SYNTHESIS, CHEMICAL-PROPERTIES AND MUTAGENICITY OF 1,6-DINITROBENZO[A]PYRENES AND 3,6-DINITROBENZO[A]PYRENES

Nitration of benzo[a]pyrene (BaP) with HN03(d= 1.38) produced a mixture of dinitroBaPs (1,6- and 3,6-isomers) and mononitroBaPs (1-, 3- and 6-isomers). Pure 1,6-dinitroBaP and 3,6-dinitroBaP were obtained by the reduction of the dinitroBaPs mixture with NaSH to yield the separable products l-amino-6-nitroBaP and 3-amino-6-nitroBaP, followed by conversion to dinitroBaPs via the the diazonium salts. The half-wave potentials (Elj2) corresponding to the one-electron reduction of dinitroBaPs were measured and the relationship of these values to the mutagenicity is discussed. © 1990, The Pharmaceutical Society of Japan. All rights reserved.