Cm. Qi et al., SYNTHESIS OF THE MANNICH-BASES OF 2-(1-CYCLOPENTENYL)CYCLOPENTANONE AND RELATED-COMPOUNDS AND EVALUATION OF THEIR ANTICANCER ACTIVITY, Medicinal chemistry research, 7(3), 1997, pp. 199-206
Nineteen novel Mannich bases of -cyclopentenyl)-5-(beta-aminomethyl)cy
clopentanone and related compounds were synthesized as potential alkyl
ating antitumor agents. The procedures involved condensation between c
yclopentanones in basic solution, the alkylation of 2-cyclopentylidene
cyclopentanone giving 6 novel 2-(1-cyclopentenyl)-2-alkylcyclopentano
nes, Mannich reaction of 2-(1-cyclopentenyl)-2-alkylcyclopentanone and
exchange reaction of arylamines for the amine of Mannich bases of 2-(
1-cyclopentenyl)cyclopentanones. Biological assays indicated that the
compounds containing cyclopentenyl, beta-aminomethyl and alpha,beta-un
saturated cycloketone side chains demonstrated significant in vitro cy
totoxicity against the tissue culture cells originating from human car
cinoma, such as KB, HCT, B16, ESCL17, A2780, BGC829, and Bel7402. Comp
ounds 5d, 5h showed therapeutic effect on mice Ehrlich ascites carcino
ma (EAC) tumors.