title: [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].
abstract: 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).
mesh_terms: D000563:Amebicides / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000627:therapeutic use / Q000633:toxicity; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000627:therapeutic use / Q000633:toxicity; D004353:Drug Evaluation, Preclinical; D004640:Emetine / Q000031:analogs & derivatives* / Q000627:therapeutic use / Q000633:toxicity; D004748:Entamoeba histolytica / Q000187:drug effects; D007942:Leukemia, Experimental / Q000188:drug therapy; D007945:Leukemia, Lymphoid / Q000188:drug therapy*; D051379:Mice
chemical_list: D000563:Amebicides; D000970:Antineoplastic Agents; D001372:Aza Compounds; D004640:Emetine
vernacular_title: 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.