The bispidine (3,7-diazabicyclo[3.3.1]nonane, C7H14N2) analogs of cisplatin, carboplatin, and oxaliplatin have been prepared. (C7H14N2)PtCl2�DMF (1b ), obtained from (1,5-hexadiene)PtCl2 and bispidine in DMF, is dimeric in the solid state. Dissolving 1b  in hot N-methyl formamide allows crystallization of the solvent-free polymeric (C7H14N2)PtCl2 (1a ). Attempts to recrystallize 1a ,b  from hot water yields the trishydrate (C7H14N2)PtCl2�3H2O (1c ). Reaction of 1  with Ag2(cbdca) (cbdca = 1,1-cyclobutane dicarboxylate) in water affords the pentahydrate (C7H14N2)Pt{C4H6(CO2)2}�5H2O (2b ), which loses water in a vacuum to give (C7H14N2)Pt{C4H6(CO2)2} (2a ). Reaction of 1  with AgNO3 in water, followed by addition of Na2C2O4, affords the water-free polymeric (C7H14N2)Pt(C2O4) (3 ). All complexes have been structurally characterized, revealing various patterns of N�H���Cl and N�H���O hydrogen bonds. In the hydrates 1c   and 2b  the complexes are embedded in intricate three-dimensional water networks. Complexes 1a , 2a , and 3  have been tested for their cytotoxicity against human cancer cell lines K562 (chronic myeloid leukemia) and A2780 (ovarian cancer). They show reduced but significant cytotoxic activity as compared to their parent analogs.

Bispidine analogs of cisplatin, carboplatin, and oxaliplatin: Synthesis, structures, and cytotoxicity

243rd National Meeting (2012)

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