Enantiomers of gamma methylene 10-deaza aminopterin and process for preparing the same

摘要

The biologically active enantiomer of gamma -methylene-10-deazaaminopterin (L-MDAM) possessing the L configuration at the gamma -methyleneglutamate moiety, which is identical to the absolute configuration at the alpha -position of the gamma -methyleneglutamic acid isolated from peanut seedlings is provided as well as procedures for its preparation. The compound does not undergo polyglutamylation, is twice as effective as an inhibitor of recombinant human dihydrofolate reductase, and exhibits outstanding growth inhibitory activity in a large variety of human tumor cells in culture. The biochemical and pharmacological results established the utility of L-MDAM as a therapeutic agent for the treatment of human neoplastic diseases.