[Synthesis of 2-formyl (acetyl) substituted quinoline thiosemicarbazones].
A series of 2-formyl (acetyl) substituted quinoline thiosemicarbazones (III, XII, XIII) were prepared in order to evaluate their antimalarial activity. Oxidation of substituted quinolines (IV) with selenium dioxide gave 2-formyl substituted quinolines (V). 2-Acetyl substituted quinoline (IX) was obtained from IV by oxidation, esterification, Claisen condensation and decarboxylation. III1-9 were synthesized by two methods; one was by condensation of 2-formyl (acetyl) substituted quinolines with methyl hydrazinecarbodithioat to form methyl-3-[1-(2-quinolinyl)-alkylidene] hydrazinecarbodithioate (XI), then the S-methyl group of XI was displaced by substituted amines to form the desired substituted thiosemicarbazones. The other was by condensation of 2-formyl (acetyl) substituted quinolines with 4-substituted-3-thiosemicarbazide (X) to afford directly III1-9, III10-12 were obtained by selective reduction of corresponding nitro compounds with stannous chloride and XII as a by-product was obtained by the nonselective reduction of III7 with stannous chloride. 3-Hexyl-4-oxothiazolin-2-yl(2-formyl or acetyl substituted quinoline) hydrazones (XIII1,2) were prepared from III1,4 via cyclization under sodium acetate condition. Eighteen compounds were found to be inactive in mice infected with ANKA strain of Plasmodium berghei.
Wang
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NH
Nanjing Institute of Materia Medica.
Wang
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R
Leng
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ZK
Peng
S X
SX
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology; D010962:Plasmodium berghei / Q000187:drug effects; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000494:pharmacology
D000962:Antimalarials; D011804:Quinolines; D013882:Thiosemicarbazones