Synthesis and cytotoxicity of betulin and betulinic acid derived 30-oxo-amides

Betulin and betulinic acid derived 30-oxo-amides were prepared by hydroboration, subsequent oxidation and amidation; these novel compounds were screened for their cytotoxic activity by SRB assays. All of the compounds showed significant cytotoxic activity for different human tumor cell lines. Small changes in the structure, however, resulted in significant changes in the cytotoxicity of the compounds. Of special interest were compounds 11 and 12, each holding an extra ethylenediamine moiety. These C-30 amides which showed low EC50 values, and both of them acted mainly by apoptosis.

Automated summary

Betulin and betulinic acid derived 30-oxo-amides were synthesized and screened for cytotoxic activity. All compounds showed significant cytotoxicity against various human tumor cell lines. Structural modifications resulted in different cytotoxicity, with compounds 11 and 12, which contained an additional ethylenediamine moiety, exhibiting low EC50 values and predominantly inducing apoptosis.