Jr. Dimmock et al., SYNTHESIS AND CYTOTOXIC EVALUATION OF SOME STYRYL KETONES AND RELATED-COMPOUNDS, European journal of medicinal chemistry, 30(3), 1995, pp. 209-217
A number of 1-aryl-4-methyl-1-penten-3-ones 1 were converted to the co
rresponding Mannich bases 2 and analogues 3. Attempts to form the azin
es 4 from several members in series 1 led to the isolation of the corr
esponding pyrazolines 5 or aryl aldehyde azines 6. Replacement of the
isopropyl group of a compound in series 1 by methyl and ethyl function
s led to ketones that reacted with hydrazine producing the correspondi
ng azines. The Mannich bases displayed greater activity than the precu
rsor ketones towards murine P388 and L1210 leukemia cells as well as t
o 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-resist
ant cell lines were shown to be free from cross resistance to a number
of the Mannich bases.