[Synthesis and antiparasitic activity of arylproprenones in the nitro-5-imidazole series]. / Synthese et activite antiparasitaire d'aryl-propenones en serie nitro-5 imidazolique.

The synthesis of new arylpropenones derived from 1-methyl-5-nitro imidazole is described. The investigation of some antiprotozoal properties has shown that compounds with the groups 4-hydroxyphenyl, 4-chlorophenyl or thiophenyl have trichomonacidal activity similar to that of metronidazole.

[Synthesis and antiparasitic activity of new nitro-5-imidazole derivatives]. / Synthèse et activité antiparasitaire de nouveaux derivés du nitro-5 imidazole.

Syntheses are given for derivatives of the type: 2-amino-1-[(1-methyl-5-nitro-2-imidazolyl) methyleneimino] imidazole, of new hydrazones of 1-methyl-5-nitroimidazole-2-carboxaldehyde and also for semicarbazones and a hydrazone of 1-methyl-5-nitro-2-(4-formyl-styryl)imidazole.

[Synthesis of new diheterocyclic derivatives of imidazole with antiparasitic activity]. / Synthèse de nouveaus dérivés dihétérocycliques de l'imidazole à activité antiparasitaire.

A description is given of potential cyclic imidazoles such as 3,3-dichloro-2-methylenimino-acrylonitrile derived from nitro or non-nitro heterocycles, as well as the hydrazone, semicarbazone and arylpropenone derivatives of the 4-chloro-2-(5-nitro-2-thienyl) (V), 5-imidazole carboxaldehyde (IV) and the 5-bromothienyl analogue. The antiparasitic activity was tested in vitro against Trichomonas vaginalis and Entameba histolytica. Some of the nitro containing compounds showed trichomonacidal activity whereas one of the non-nitro compounds with potential imidazole structure showed clear amebacidal activity. This compound, 3,3-dichloro-2-methyleneimino acrylonitrile has anti-ameba activity comparable with that of metronidazole.

[Azotized emetine analogues: synthesis and evaluation of the anti-amebic and anti-tumoral action of aza-3 emetine and attempted synthesis of aza-2 emetine]. / Analogues azotés de l'émétine: synthèse et évaluation de l'activite antiamibienne et antitumorale de l'aza-3 émétine, et essais d'obtention de l'aza-2 émétine.

The synthesis of the N,N-bis-(acetylhomoveratrylamido)-1-hydroxymethyl and 1-carboxypropylamines (III a) and (III b) is described. Until now, these molecules could not been cyclized to the corresponding isoquinoline compounds. An attempted synthesis of 3-azaemetine by condensing homoveratrylamine with acetonedicarboxylic acid or its esters did not yield the expected diamide (XIV). However, by subjecting 1,3-bis-(1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolyl)acetone (XV) to a reducing aminoalkylation, one obtained the corresponding ethylamino derivative (XVI) which could be cyclized through Mannich reaction to give 3-azaemetine. The pharmacological screening showed 3-azaemetine to be less toxic than emetine in the mouse and without antiamebic and antitumor activity against P 388 Leukaemia in the mouse (25).