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A series of carbonyl derivatives of tilorone was synthetized by reaction with appropriate amino compounds, mainly hydrazines and hydrazides. The condensation products obtained were tested for cancerostatic activity against the murine leucaemia L 1210 and the Walker carcinosarcoma of the rat. Only three of the substances under investigation (1a, 5, 13) proved active against the Walker carcinosarcoma, one of which (5) being comparable to tilorone. No activity against L 1210 was observed, even tilorone exerted no effect. The reduction in activity against the Walker carcinosarcoma which resulted from the carbonyl substitution might be caused by a decrease in the ability to intercalate into DNA.

Tilorone (free base) reacts with alkyl halides forming quaternary ammonium salts. Bis- as well as mono quaternary compounds (2 resp. 3) were synthesized. The tilorone-bis-methoiodide (2a) was converted to several carbonyl derivatives (4 and 5). All produced compounds did not show any cytostatic activity against the murine leukemias L 1210 and P 388 in vivo. Especially the bis-quaternary derivatives 2 were highly toxic in the mouse.