7-Aminoaziridinomitosenes: Synthesis, Structure, and Chemistry

Article abstract of DOI:10.1021/jo00015a016

7-Aminoleucoaziridinomitosene (2a) has been proposed as a key intermediate in the reductive activation process for the antineoplastic agent, mitomycin C (1a).Little is known about 2a and its oxidised equivalent, 7-aminoaziridinomitosene (3a).An expedient electrochemical procedure for 3a and the corresponding N-methyl analogue 3b has been developed.NMR spectral studies of 3a in DMF-d7 and DMSO-d6 provided important information concerning the solution-state structure for this adduct.Factors controlling the aziridine ring-opening process under reductive and nonreductive conditions have been determined, as well as evidence for the intermediacy of 2a in the reductive activation cascade of 1a.