title: Antimalarials. 11. 2-Vinylogs of substituted 2-aryl-4-quinoline amino alcohols.
abstract: 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.
mesh_terms: D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000627:therapeutic use; D009682:Magnetic Resonance Spectroscopy; D008288:Malaria / Q000188:drug therapy; D013058:Mass Spectrometry; D051379:Mice; D010962:Plasmodium berghei; D011804:Quinolines / Q000138:chemical synthesis* / Q000627:therapeutic use; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000627:therapeutic use
chemical_list: D000962:Antimalarials; D011804:Quinolines; D014753:Vinyl Compounds