Synthesis and cytotoxic evaluation of some styryl ketones and related compounds

Abstract

Summary A number of 1-aryl-4-methyl-1-penten-3-ones 1 were converted to the corresponding Mannich bases 2 and analogues 3 . Attempts to form the azines 4 from several members in series 1 led to the isolation of the corresponding pyrazolines 5 or aryl aldehyde azines 6 . Replacement of the isopropyl group of a compound in series 1 by methyl and ethyl functions led to ketones that reacted with hydrazine producing the corresponding azines. The Mannich bases displayed greater activity than the precursor ketones towards murine P388 and L1210 leukemia cells as well as to a panel of human tumour cell lines. Certain of the Mannich bases had selective toxicity towards some human tumour cell lines and others to L1210 cells (in contrast to human T lymphocytes). Several drug-resistant cell lines were shown to be free from cross resistance to a number of the Mannich bases.