Lutz R E, Sanders J M
J Med Chem. 1976 Mar;19(3):407-10. doi: 10.1021/jm00225a014.
3-(P-Chlorobenzylidene)-5, 7-dimethyl-2, 3-dihydro-1H-cyclopenta[b]quinoline-9-(di-n-butylaminomethyl)methanol and 2-[beta-(p-chlorostyryl)]-6, 8-dimethylquinoline-4-(di-n-butylaminomethyl)methanol were synthesized from 6, -8-dimethyl-4-hydroxycarbostyril by 3, 3-dichlorination, dimethoxylation th the 3-ketal, basic hydrolysis to the glyoxal acetal, Pfitzinger condensation with cylopentanone or acetone to the 2, 3-trimethylene or 2-methylquinoline, condensation with p-ClPhCHO at the 2-methylene or 2-methyl group, hydrolysis to the 4-quinaldehyde, methylenation to the epoxide, and condensation with Bu2NH. Both were curative against P. berghei in mice. The first was the more effective: active at 10 mg/kg, completely curative at 40 mg/kg, and only mildly phototoxic in animals.
