Acta Pharm. 54 (2004) 133-142[ Full paper in PDF ]
Reaction of 1-oxo-1,2,3,4-tetrahydrocarbazoles (1a-e) with hydrazine hydrate in absolute ethanol afforded N,N'-biscarbazolylazine derivatives (2a-e). Treatment of 1-oxo-1,2,3,4-tetrahydrocarbazoles (1a-e) with hydroxylamine hydrochloride in ethanol with a catalytic amount of pyridine resulted in the formation of 1-hydroxyimino-1,2,3,4-tetrahydrocarbazoles (3a-e). Reduction of 3 with hydrazine hydrate in the presence of palladized carbon afforded N,N'-carbazolyl hydrazine derivatives (4a-e). The newly formed compounds were characterized by IR, 1H NMR, mass spectra and by elemental analysis. All compounds proved to have great potentialities as antibacterial and antifungal agents due to the presence of the azine or the hydrazine group. Particularly, the chloro substituted derivatives 2e and 4e showed excellent antibacterial and antifungal activity.
Keywords: 1-oxo-1,2,3,4-tetrahydrocarbazoles, 1-hydroxyimino-1,2,3,4-tetrahydrocarbazoles, N,N'-biscarbazolylazines, N,N'-carbazolylhydrazines, antibacterial, antifungal activity