Synthesis and structure-activity relationship studies of cytotoxic epoxide derivatives of 7-oxabicyclo[2.2.1]heptane.

Abstract

Dimethyl exo-5,6-oxido-7-oxabicyclo[2.2.1]hept-2-ene-2,3-dicarboxylate (1) and the 1-methyl homologue 2 were shown to exhibit significant cytotoxicity in the 9KB tissue culture assay. Several analogues of 1 were prepared and it was found that removal of the epoxide, or the oxygen bridge, or the 2,3 double bond from 1 resulted in loss of significant cytotoxic activity. One compound which lacked the epoxide moiety, dimethyl 1-methyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate (5), also exhibited marginal cytotoxic activity.

Cite this paper

@article{Anderson1977SynthesisAS, title={Synthesis and structure-activity relationship studies of cytotoxic epoxide derivatives of 7-oxabicyclo[2.2.1]heptane.}, author={W. Kyle Anderson and Raymond Dewey}, journal={Journal of medicinal chemistry}, year={1977}, volume={20 2}, pages={306-8} }