Synthesis and antibacterial activity of some nitrobenzimidazoles and 2(3H)-benzimidazolones.
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Biomedical subjects
Publications and source records attributed to I Nabih.
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The synthesis of a new class of compounds structurally related to cyclohexenothiaxanthones and benzothiaxanthones including a pyridine ring is described in an attempt to find compounds that may have schistosomicidal and carcinostatic activity. Synthesis was achieved through the condensation of amino-cyclohexenothiaxanthones and amino-benzothiaxanthones with ethyl acetoacetate by the Knorr and Conrad-Limpach methods.
3-Ethylaminomethyl-2-methyl-4(1H)-quinolone (1a) and its 6-CH3, 6-OCH3, and 7-Cl derivatives were prepared by means of the Mannich reaction. Conversion to the 4-chloro derivatives and condensation with 3-chloroaniline gave the corresponding 4-(3-chloroanilino) derivatives. Cyclization of 4-(3-chloroanilino)-2,6-dimethyl-3-ethyl-aminomethylquinoline (3a) and its 6-OCH3 derivative with paraformaldehyde gave 1-(3-chlorophenyl)-3,9-dimethyl-3-ethyltetrahydropyrimido[5,4-c]quinoline (4a) and the 9-OCH3 derivative 4b. Treatment of 4b with benzaldehyde gave 1-(3-chlorophenyl)-3-ethyl-9-methoxy-5-styryltetrahydropyrimido[5,4-c]quinoline (5). 3-Benzylaminomethyl-6-methoxy-2-methyl-4(1H)-quinolone (1e) and 3,3'-(1,3-benzyliminodimethylene)di[2-methyl-4(1H)-quinolone] (6b) were also synthesized. The compounds were inactive as antimalarials.
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(4-Quinolinoamino)aminoalkyltetrahydronaphthalene derivatives were synthesized in an attempt to introduce new agents with antimalarial activity.
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