Quinolizidine derivatives with antitubercular activity

By reacting lupinylmagnesium chloride with suitable aromatic ketones, several lupinyldiarylcarbinols were obtained, whose dehydration gave the corresponding lupinylidenediarylmethanes. By reduction of three of these unsaturated compounds, the corresponding lupinyldiarylmethanes were also obtained. Direct condensation of lupinine with fluorene gave the 9-epi- lupinylfluorene. The quinolizidine derivatives obtained were tested against Mycobacterium tuberculosis H37RV. Nine compounds resulted endowed with good antitubercular activity with MIC<8 μg/ml, while the remaining were only moderately active. Most interesting was the lupinylidene derivative 13 with MIC > 0.1 < 0.5 μg/ml.