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The 4-quinolone-2-carbohydrazide 6a was converted into 1-aryl-3-(4-quinolon-2-yl)ureas 5a, 5b, 5c, 5d, 5e, 1-aryl-3-(4-quinolon-2-yl)imidazolidine-2,4-diones 9a, 9b, and N-(4-quinolon-2-yl)carbamates 10a, 10b via 4-quinolone-2-carbonylazide 7a. The 4-methoxyquinoline-2-carbohydrazide 6b was also transformed into 1-aryl-3-(4-methoxyquinolin-2-yl)ureas 11a, 11b, 11c, 11d, 1-aryl-3-(4-methoxyquinolin-2-yl)imidazolidine-2,4-diones 12a, 12b, and N-(4-methoxyquinolin-2-yl)carbamates 13a, 13b via 4-methoxyquinoline-2-carbonylazide 7b. Some of the 1-aryl-3-(4-quinolon-2-yl)ureas 5a, 5b, 5c, 5d, 5e showed the in vitro antimalarial activity to chloroquine-resistant Plasmodium falciparum, wherein IC50 was 0.93 to 4.00 μM. [ABSTRACT FROM AUTHOR]

The 1-hydrazinocarbonylmethyl-4-quinolone-3-carboxylate ( 10) was converted into the 1-(4-amino-1,2,4-triazol-3-ylmethyl)-4-quinolone-3-carboxylic acid ( 13), whose reaction with arylcarbaldehydes gave the 1-(4-arylmethyleneamino-1,2,4-triazol-3-ylmethyl)-4-quinolone-3-carboxylic acids ( 5a, 5b, 5c, 5d, 5e, 5f, 5g). Compound 10 was also transformed into the 1-(4-amino-1,2,4-triazol-3-ylmethyl)-4-quinolone-3-carbohydrazide ( 15), whose reaction with phenyl isocyanate or phenyl isothiocyanate afforded the 4-phenyl-1-(1-triazolylmethyl-4-quinolon-3-ylcarbonyl)semicarbazide ( 6a) or 4-phenyl-1-(1-triazolylmethyl-4-quinolon-3-ylcarbonyl)thiosemicarbazide ( 6b), respectively. Compounds 6a, 6b showed the in vitro antimalarial activity to chloroquine-resistant Plasmodium falciparum, wherein their IC50 was 3.89 and 3.91 μM, respectively. [ABSTRACT FROM AUTHOR]