Synthesis and antitumor activity of cis-dichloridoplatinum(II) complexes of 1,1'-biisoquinolines.
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.
Kuo
Chen-Yuan
CY
Department of Biological Science and Technology, Yung-Ta Institute of Technology and Commerce, 316 JhongShan Road, Pingtung 909, Taiwan, ROC. cchlin@mail.nchu.edu.tw
Wu
Ming-Jung
MJ
Lin
Chu-Chieh
CC
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D007097:Imines / Q000737:chemistry; D020128:Inhibitory Concentration 50; D007546:Isoquinolines / Q000737:chemistry*; D009944:Organoplatinum Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000970:Antineoplastic Agents; D007097:Imines; D007546:Isoquinolines; D009944:Organoplatinum Compounds; C039109:isoquinoline