Synthesis and antitumor activity of cis-dichloridoplatinum(II) complexes of 1,1′-biisoquinolines

Article abstract of DOI:10.1016/j.ejmech.2009.09.023

A simple approach to 1,1′,2,2′,3,3′,4,4′-octahydro-1,1′-biisoquinolines is described. Reaction of phenethylamines with oxalyl chloride led to N,N′-bis(phenethyl) oxamides (1). Cyclization of oxamides by using Bischler - Napieralski conditions gave 3,3′,4,4′-tetrahydro-1,1′-biisoquinoline(3) and unusual products 2, 4, 5. Reduction of 3,3′,4,4′-tetrahydro-1,1′-biisoquinolines with sodium boron hydride gave both rac-1,1′,2,2′,3,3′,4,4′-octahydro-1,1′-biisoquinolines(6) and meso-1,1′,2,2′,3,3′,4,4′ -octahydro-1,1′-biisoquinolines(7). Compound 6 was resolved to (1S, 1S′) (8) and (1R, 1R′) (9) furtherly. By treating all the biisoquinolines with K₂PtCl₄ afforded their cis-dichloridoplatinum (II) complexes (12-18). The antitumor activity of these complexes was evaluated.