Evaluation of some azines of aminomethylacetophenones and related quaternary ammonium compounds versus the EMT6 tumour.

Azines derived from 3-dimethylamino-1-phenyl-1-propanone hydrochloride and two ring dimethylaminomethyl-acetophenones as well as the related quaternary ammonium iodides were synthesized. In phosphate buffer ph 7.4/37 degrees C 3-dimethylamino-1-phenyl-1-propanone azine dimethoiodide (2) formed 1-phenyl-3-(3-phenyl-2-pyrazolin-1-yl)-1-propanone. In the presence of a biomimetic thiol, 2-mercaptoethanol, compound 2 gave a bis S-alkylated product namely 3-(2-hydroxyethylthio)-1-phenyl-1-propanone azine. New products were not observed when two quaternary ammonium compounds derived from ring aminomethylacetophenone azines were examined under similar conditions. Six derivatives had moderate activity against the EMT6 tumour in vitro at concentrations of 250-500 mumol.1(-1) and greatest potency was noted with the ring dimethylaminomethylacetophenone azines and related quaternary ammonium compounds at these concentrations.